異氰基乙酸乙酯

異氰基乙酸乙酯
英文名	Ethyl isocyanoacetate
識別
CAS編號	2999-46-4
PubChem	533707
SMILES	CCOC(=O)C[N+]#[C-];
InChI	1S/C5H7NO2/c1-3-8-5(7)4-6-2/h3-4H2,1H3;
InChIKey	FPULFENIJDPZBX-UHFFFAOYSA-N
性質
化學式	C5H7NO2
摩爾質量	113.11 g·mol−1
外觀	黃色油狀液體
沸點	76—78 °C（349—351 K）（4 mmHg）; 80—82 °C（353—355 K）（12 mmHg）
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

異氰基乙酸乙酯是一種有機化合物，化學式為C₅H₇NO₂。根據一份2020年的統計，它是在學術研究中第五常見的異腈。^[3]它可由N-甲酰基甘氨酸乙酯和光氣（或三氯氧磷^[4]）在三乙胺存在下於二氯甲烷中反應得到。^[2]

反應

異氰基乙酸乙酯在催化下和乙醛反應，可以得到4,5-二氫-5-甲基-4-噁唑甲酸甲酯，反應同時產生4S-反式異構體和4R-順式異構體，比例84:16。^[5]它和己醛在對甲苯磺酸鈉存在下於水中反應，可以得到N-(2-羥基-1-氧代庚基)甘氨酸乙酯。^[6]

它在氫氧化鉀溶液中水解，生成異氰基乙酸鉀。^[7]

CNCH₂COOC₂H₅ + KOH → CNCH₂COOK + C₂H₅OH

它和磺酰氯在三氯甲烷中反應，可以得到N-二氯亞甲基甘氨酸乙酯。^[8]

在氯化銅、鄰菲囉啉和碳酸銫存在下，它和芳胺、二氟氯乙酸鈉反應，可以得到相應的芳基咪唑甲酸乙酯。^[9]

參考文獻

^ ^1.0 ^1.1 Novotortsev, Vladimir K.; Kukushkin, Maxim E.; Tafeenko, Viktor A.; Skvortsov, Dmitry A.; Kalinina, Marina A.; Timoshenko, Roman V.; Chmelyuk, Nelly S.; Vasilyeva, Liliya A.; Tarasevich, Boris N.; Gorelkin, Petr V.; Erofeev, Alexander S.; Majouga, Alexander G.; Zyk, Nikolai V.; Beloglazkina, Elena K. Dispirooxindoles Based on 2-Selenoxo-Imidazolidin-4-Ones: Synthesis, Cytotoxicity and ROS Generation Ability. International Journal of Molecular Sciences. 5 March 2021, 22 (5): 2613 [2022-08-02]. PMC 7961907 . PMID 33807662. doi:10.3390/ijms22052613. eISSN 1422-0067. （原始內容存檔於2022-06-17）.
^ ^2.0 ^2.1 Ugi, I.; Fetzer, U.; Eholzer, U.; Knupfer, H.; Offermann, K. Isonitrile Syntheses. Angewandte Chemie International Edition. June 1965, 4 (6): 472–484 [2022-08-02]. ISSN 0570-0833. doi:10.1002/anie.196504721. eISSN 1521-3773. （原始內容存檔於2022-03-05）.
^ Patil, Pravin; Ahmadian-Moghaddam, Maryam; Dömling, Alexander. Isocyanide 2.0. Green Chemistry. 2020, 22 (20): 6902–6911 [2022-08-02]. ISSN 1463-9262. doi:10.1039/D0GC02722G. eISSN 1463-9270. （原始內容存檔於2022-06-29）.
^ Matsuo, Takashi; Hayashi, Akihiro; Abe, Masato; Matsuda, Takaaki; Hisaeda, Yoshio; Hayashi, Takashi. Meso-Unsubstituted Iron Corrole in Hemoproteins: Remarkable Differences in Effects on Peroxidase Activities between Myoglobin and Horseradish Peroxidase. Journal of the American Chemical Society. 7 October 2009, 131 (42): 15124–15125. ISSN 0002-7863. PMID 19810701. doi:10.1021/ja907428e. eISSN 1520-5126.
^ Matsumoto, Kazuo; Suzuki, Mamoru. Ethyl isocyanoacetate. e-EROS Encyclopedia of Reagents for Organic Synthesis. 2001: 1–3. CODEN 69KUHI.
^ Sela, Tal; Vigalok, Arkadi. Salt‐Controlled Selectivity in “on Water” and “in Water” Passerini‐Type Multicomponent Reactions. Advanced Synthesis & Catalysis. 22 August 2012, 354 (13): 2407–2411 [2022-08-04]. ISSN 1615-4150. doi:10.1002/adsc.201200448. eISSN 1615-4169. （原始內容存檔於2022-08-04）.
^ Wang, Jian; Zhong, Ling; Tang, Shi; Liu, Yuan; Ding, Shumin; Li, Lianjie; Zhao, Haixia; Chen, Chen; Shang, Yongjia. Palladium-Catalyzed Divergent Imidoylative Cyclization of Multifunctionalized Isocyanides: Tunable Access to Oxazol-5(4H)-ones and Cyclic Ketoimines. The Journal of Organic Chemistry. 6 May 2020, 85 (11): 7297–7308 [2022-08-04]. ISSN 0022-3263. PMID 32370499. doi:10.1021/acs.joc.0c00672. eISSN 1520-6904. （原始內容存檔於2022-08-04）.
^ Gober, Claire M.; Le, Hoang V.; Ganem, Bruce. A simple, general synthesis of carbonimidic dichlorides. Tetrahedron Letters. August 2012, 53 (34): 4536–4537. ISSN 0040-4039. PMC 3409665 . PMID 22865938. doi:10.1016/j.tetlet.2012.06.046.
^ Wang, Ya; Zhou, Yao; Song, Qiuling. [3+1+1] type cyclization of ClCF₂COONa for the assembly of imidazoles and tetrazoles via in situ generated isocyanides. Chemical Communications. 2020, 56 (45): 6106–6109 [2022-08-04]. ISSN 1359-7345. PMID 32356534. doi:10.1039/d0cc01919d. eISSN 1364-548X. （原始內容存檔於2022-03-07）.

[Novotortsev-1] 1.0 ^1.1 Novotortsev, Vladimir K.; Kukushkin, Maxim E.; Tafeenko, Viktor A.; Skvortsov, Dmitry A.; Kalinina, Marina A.; Timoshenko, Roman V.; Chmelyuk, Nelly S.; Vasilyeva, Liliya A.; Tarasevich, Boris N.; Gorelkin, Petr V.; Erofeev, Alexander S.; Majouga, Alexander G.; Zyk, Nikolai V.; Beloglazkina, Elena K. Dispirooxindoles Based on 2-Selenoxo-Imidazolidin-4-Ones: Synthesis, Cytotoxicity and ROS Generation Ability. International Journal of Molecular Sciences. 5 March 2021, 22 (5): 2613 [2022-08-02]. PMC 7961907 . PMID 33807662. doi:10.3390/ijms22052613. eISSN 1422-0067. （原始內容存檔於2022-06-17）.

[Ugi-2] 2.0 ^2.1 Ugi, I.; Fetzer, U.; Eholzer, U.; Knupfer, H.; Offermann, K. Isonitrile Syntheses. Angewandte Chemie International Edition. June 1965, 4 (6): 472–484 [2022-08-02]. ISSN 0570-0833. doi:10.1002/anie.196504721. eISSN 1521-3773. （原始內容存檔於2022-03-05）.

[Patil-3] Patil, Pravin; Ahmadian-Moghaddam, Maryam; Dömling, Alexander. Isocyanide 2.0. Green Chemistry. 2020, 22 (20): 6902–6911 [2022-08-02]. ISSN 1463-9262. doi:10.1039/D0GC02722G. eISSN 1463-9270. （原始內容存檔於2022-06-29）.

[Matsuo-4] Matsuo, Takashi; Hayashi, Akihiro; Abe, Masato; Matsuda, Takaaki; Hisaeda, Yoshio; Hayashi, Takashi. Meso-Unsubstituted Iron Corrole in Hemoproteins: Remarkable Differences in Effects on Peroxidase Activities between Myoglobin and Horseradish Peroxidase. Journal of the American Chemical Society. 7 October 2009, 131 (42): 15124–15125. ISSN 0002-7863. PMID 19810701. doi:10.1021/ja907428e. eISSN 1520-5126.

[5] Matsumoto, Kazuo; Suzuki, Mamoru. Ethyl isocyanoacetate. e-EROS Encyclopedia of Reagents for Organic Synthesis. 2001: 1–3. CODEN 69KUHI.

[6] Sela, Tal; Vigalok, Arkadi. Salt‐Controlled Selectivity in “on Water” and “in Water” Passerini‐Type Multicomponent Reactions. Advanced Synthesis & Catalysis. 22 August 2012, 354 (13): 2407–2411 [2022-08-04]. ISSN 1615-4150. doi:10.1002/adsc.201200448. eISSN 1615-4169. （原始內容存檔於2022-08-04）.

[7] Wang, Jian; Zhong, Ling; Tang, Shi; Liu, Yuan; Ding, Shumin; Li, Lianjie; Zhao, Haixia; Chen, Chen; Shang, Yongjia. Palladium-Catalyzed Divergent Imidoylative Cyclization of Multifunctionalized Isocyanides: Tunable Access to Oxazol-5(4H)-ones and Cyclic Ketoimines. The Journal of Organic Chemistry. 6 May 2020, 85 (11): 7297–7308 [2022-08-04]. ISSN 0022-3263. PMID 32370499. doi:10.1021/acs.joc.0c00672. eISSN 1520-6904. （原始內容存檔於2022-08-04）.

[8] Gober, Claire M.; Le, Hoang V.; Ganem, Bruce. A simple, general synthesis of carbonimidic dichlorides. Tetrahedron Letters. August 2012, 53 (34): 4536–4537. ISSN 0040-4039. PMC 3409665 . PMID 22865938. doi:10.1016/j.tetlet.2012.06.046.

[9] Wang, Ya; Zhou, Yao; Song, Qiuling. [3+1+1] type cyclization of ClCF₂COONa for the assembly of imidazoles and tetrazoles via in situ generated isocyanides. Chemical Communications. 2020, 56 (45): 6106–6109 [2022-08-04]. ISSN 1359-7345. PMID 32356534. doi:10.1039/d0cc01919d. eISSN 1364-548X. （原始內容存檔於2022-03-07）.

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