ethyl 3-phenyl-3-isocyanatopropanoate | 88636-83-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-phenyl-3-isocyanatopropanoate
• 英文别名: 3-isocyanato-3-phenyl-propionic acid ethyl ester；3-Isocyanato-3-phenyl-propionsaeure-aethylester；(+/-)-3-Isocyanato-3-phenyl-propionsaeureaethylester；Ethyl 3-isocyanato-3-phenylpropanoate
• CAS: 88636-83-3
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: FIILOKZYNQADIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  ethyl 3-phenyl-3-isocyanatopropanoate 在 盐酸 、 lithium hydroxide 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 37.0h， 生成 lithium;N-[(2-carboxy-1-phenylethyl)carbamoyl]-2-[4-[(2-methylphenyl)carbamoylamino]phenyl]-N-(2-methylpropyl)ethanehydrazonate
  参考文献：
  名称：

  Design and Synthesis of Potent and Selective Inhibitors of Integrin VLA-4

  摘要：

  The synthesis and identification of a novel series of inhibitors of integrin VLA-4 are described. Their in vitro activity and selectivity against closely related integrins are also presented. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00586-8
• 作为产物：
  描述：

  DL-3-氨基-3-苯基丙酸 在 三甲基氯硅烷 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 ethyl 3-phenyl-3-isocyanatopropanoate
  参考文献：
  名称：

  Organosilicon synthesis of isocyanates: IV. Synthesis of isocyanates from aliphatic and alkylaromatic amino acid esters

  摘要：

  Treatment of an alcoholic suspension of amino acids with trimethylchlorosilane yielded phenylglycine, valine, beta-phenylalanine, and homovaline ester hydrochlorides. Their saccharin-catalyzed silylation with hexamethyldisilazane proceeds quantitatively and involves only one proton of the amino group. The best conversion of the amino acid esters to the corresponding isocyanates was achieved by phosgene treatment of their monosilyl urethanes, rather than of the silylated amino esters. Monosilyl urethanes are formed quantitatively by treatment of the amino acid ester hydrochlorides with the hexamethyldisilazane-CO2 system. The H-1 NMR spectra show that monosilyl urethanes derived from alpha- and beta-amino acid esters are characterized by intramolecular interaction of the silicon atom and the oxygen atom of the carboxy group.

  DOI：

  10.1134/s1070363207040135

文献信息

• Diacetamides—I
  作者：A. Kornhauser、D. Keglević

  DOI：10.1016/0040-4020(62)80018-0

  日期：1962.1

  The action of boiling acetic anhydride on β-ureidesters, β-N-carbonyl esters and β-amino-esters was studied. It was shown that no cyclization of β-ureidoesters occurred and that N,N-diacetyl and N-acetyl-β-aminoesters were the reaction products in all three cases. A satisfactory separation of these compounds by chromatography was achieved and their physical properties determined. The mechanism of the

  研究了乙酸酐沸腾对β-脲酯，β-N-羰基酯和β-氨基酯的作用。结果表明，没有发生β-脲基酯的环化，并且在所有三种情况下，N，N-二乙酰基和N-乙酰基-β-氨基酯都是反应产物。通过色谱法令人满意地分离了这些化合物，并确定了它们的物理性质。简要讨论了反应机理。
• Organosilicon synthesis of isocyanates: III. Synthesis of aliphatic, carbocyclic, aromatic, and alkylaromatic isocyanatocatboxylic acid esters
  作者：A. V. Lebedev、A. B. Lebedeva、V. D. Sheludyakov、S. N. Ovcharuk、E. A. Kovaleva、O. L. Ustinova

  DOI：10.1134/s1070363206070115

  日期：2006.7

  A series of aminoacid esters was prepared by treating the aminoacid suspensions in ethanol with thionyl chloride. Best conversion of aminoacid esters to corresponding isocyanates was achieved in the case of aromatic and carbocyclic aminoesters by phosgeneation of their N-silyl derivatives, and in the case of aliphatic and alkylaromatic aminoesters by phosgeneation of O-silyl or N,O-bissilylurethanes on their basis. In the last case additional step of esterification of the by-products isocyanatoalkylcarboxylic acid chlorides is reqired after phosgeneation. Unusual generation of cynnamates and intramolecular N -> O-migration of trimethylsilyl group in the solutions of silylated alkylaromatic beta-aminoacid esters were found.
• Über β-Isocyanat-fettsäureester und einige ihrer Reaktionsprodukte
  作者：K. Schlögl

  DOI：10.1007/bf00900623

  日期：1958.1
• Design and Synthesis of Potent and Selective Inhibitors of Integrin VLA-4
  作者：Sompong Wattanasin、Beat Weidmann、Didier Roche、Stewart Myers、Amy Xing、Qin Guo、Michael Sabio、Peter von Matt、Ronald Hugo、Susan Maida、Philip Lake、Marla Weetall

  DOI：10.1016/s0960-894x(01)00586-8

  日期：2001.11

  The synthesis and identification of a novel series of inhibitors of integrin VLA-4 are described. Their in vitro activity and selectivity against closely related integrins are also presented. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Organosilicon synthesis of isocyanates: IV. Synthesis of isocyanates from aliphatic and alkylaromatic amino acid esters
  作者：A. V. Lebedev、A. B. Lebedeva、V. D. Sheludyakov、V. V. Shatunov、S. N. Ovcharuk

  DOI：10.1134/s1070363207040135

  日期：2007.4

  Treatment of an alcoholic suspension of amino acids with trimethylchlorosilane yielded phenylglycine, valine, beta-phenylalanine, and homovaline ester hydrochlorides. Their saccharin-catalyzed silylation with hexamethyldisilazane proceeds quantitatively and involves only one proton of the amino group. The best conversion of the amino acid esters to the corresponding isocyanates was achieved by phosgene treatment of their monosilyl urethanes, rather than of the silylated amino esters. Monosilyl urethanes are formed quantitatively by treatment of the amino acid ester hydrochlorides with the hexamethyldisilazane-CO2 system. The H-1 NMR spectra show that monosilyl urethanes derived from alpha- and beta-amino acid esters are characterized by intramolecular interaction of the silicon atom and the oxygen atom of the carboxy group.