3-phenyl-aziridine-2-carboxylic acid amide | 79559-52-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-phenyl-aziridine-2-carboxylic acid amide
• 英文别名: 3-Phenyl-aziridin-2-carbonsaeure-amid；(2S,3S)-3-Phenylaziridine-2-carboxamide；3-phenylaziridine-2-carboxamide
• CAS: 79559-52-7
• 化学式: C₉H₁₀N₂O
• 分子量: 162.191
• InChiKey: GPBCRRMRLBDOKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  65
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenyl-aziridine-2-carboxylic acid amide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 60.0 ℃ 、5.52 MPa 条件下， 反应 14.0h， 生成 alpha-氨基-苯丙酰胺
  参考文献：
  名称：

  Synthesis of .alpha.-halocinnamate esters via solvolytic rearrangement of trichloroallyl alcohols

  摘要：

  Aryl trichlorovinyl ketones undergo regioselective reduction to the corresponding carbinols with sodium borohydride in alcoholic solvents and are transformed to the (Z)-alpha-chlorocinnamate ester derivatives via an acid-catalyzed allylic rearrangement. Michael addition of ammonia to these ester derivatives affords cis- and/or trans-aziridine amides. The facile rearrangement allows the synthesis of d,l-phenylalanine derived from perchloroethylene and toluene.

  DOI：

  10.1021/jo00010a027
• 作为产物：
  描述：

  肉桂腈 在 硫酸 、 potassium tert-butylate 、 氨 、 溴 作用下， 以 二甲基亚砜 为溶剂， 反应 240.0h， 生成 3-phenyl-aziridine-2-carboxylic acid amide
  参考文献：
  名称：

  3-氟苯丙氨酸及其衍生物的新型合成

  摘要：

  发现2-氰基-3-苯基氮丙啶和2-酰胺基-3-苯基氮丙啶通过HF /吡啶的开环分别得到2-氨基-3-氟苯基丙腈（IV）和2-氨基-3-氟苯基丙酰胺（VII）。3-氟苯丙氨酸（V）可通过（IV）或（VII）的酸性水解获得，而异丙基-3氟苯丙氨酸盐（VI）可通过（V）的酯化或与异丙醇-12 NHCl加热（IV）来分离在回流下。

  DOI：

  10.1016/s0022-1139(00)82305-2

文献信息

• PROCESS FOR PREPARING BETA-HYDROXY AMINO ACID
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0079390A1

  公开（公告）日：1983-05-25

  A process for preparing a β-hydroxy amino acid, which comprises adsorbing aziridine-2-carboxylic acid or derivatives thereof represented by the following general formula (II) wherein R, represents hydrogen atom, a methyl group, a substituted or unsubstituted phenyl or pyridyl group, R2 represents a hydrogen atom or a methyl group, X represents -C02H, -CO2M (wherein M represents an alkali metal or alkaline earth metal), -CO2R3 (wherein R3 represents a lower alkyl group containing 1 to 5 carbon atoms or an aralkyl group), -CONH2 or -CN, except for the case where R, and R2 both represent a hydrogen atom and X represents CO2H or C02M, onto a strongly acidic cation-exchange resin, and heating in the presence of water. Examples of the β-hydroxy amino acid include DL-serine, threonine, β-hydroxyvaline, and β-hydroxyphenylalanine.

  一种制备β-羟基氨基酸的工艺，它包括吸附氮丙啶-2-羧酸或由下通式(II)代表的其衍生物 其中 R 代表氢原子、甲基、取代或未取代的苯基或吡啶基，R2 代表氢原子或甲基，X 代表 -C02H、-CO2M（其中 M 代表碱金属或碱土金属）、-CO2R3（其中 R3 代表含有 1 至 5 个碳原子的低级烷基或芳烷基）、-CONH2 或 -CN，但 R 和 R2 均代表氢原子且 X 代表 CO2H 或 C02M 的情况除外。β-羟基氨基酸的例子包括 DL-丝氨酸、苏氨酸、β-羟基缬氨酸和 β-羟基苯丙氨酸。
• Yukawa; Kimura, Memoirs of the Institute of Scientific and Industrial Research, Osaka University, 1957, vol. 14, p. 191,193
  作者：Yukawa、Kimura

  DOI：——

  日期：——
• METHOD OF SYNTHESIZING ALPHA-AMINO ACID DERIVATIVES
  申请人：Nanjing Tech University

  公开号：US20200361863A1

  公开（公告）日：2020-11-19

  Disclosed is a method of synthesizing an α-amino acid derivative, where an azirine compound, used as raw material, is reacted with a sulfhydryl compound in a mixed system of an organic solvent and a buffer solution under the protection of nitrogen to produce the α-amino acid derivative. In the reaction, the carbon-nitrogen double bond of the azirine compound is attacked by the sulfhydryl compound, so that the azirine compound is directly opened to form the α-amino acid derivative of which the same carbon atom is added with two molecules of the sulfhydryl compound. This method can be performed directly in an aqueous phase without using a metal catalyst.
• Synthesis of .alpha.-halocinnamate esters via solvolytic rearrangement of trichloroallyl alcohols
  作者：William J. Kruper、Albert H. Emmons

  DOI：10.1021/jo00010a027

  日期：1991.5

  Aryl trichlorovinyl ketones undergo regioselective reduction to the corresponding carbinols with sodium borohydride in alcoholic solvents and are transformed to the (Z)-alpha-chlorocinnamate ester derivatives via an acid-catalyzed allylic rearrangement. Michael addition of ammonia to these ester derivatives affords cis- and/or trans-aziridine amides. The facile rearrangement allows the synthesis of d,l-phenylalanine derived from perchloroethylene and toluene.
• A novel synthesis of 3-fluorophenylalanine and some of its derivatives
  作者：A.I. Ayi、M. Remli、R. Guedj

  DOI：10.1016/s0022-1139(00)82305-2

  日期：1981.7

  Ring opening of 2-cyano-3-phenylaziridine and 2-amido-3-phénylaziridine by HF/pyridine was found to give 2-amino-3-fluorophenylpropionitrile (IV) and 2-amino-3-fluorophenylalanamide (VII) respectively. 3-fluorophenylalanine (V) could be obtained by an acidic hydrolysis of (IV) or (VII) whereas isopropyl-3 fluorophenylalanate (VI) was isolated by esterification of (V) or by heating (IV) with iso-propanal-12

  发现2-氰基-3-苯基氮丙啶和2-酰胺基-3-苯基氮丙啶通过HF /吡啶的开环分别得到2-氨基-3-氟苯基丙腈（IV）和2-氨基-3-氟苯基丙酰胺（VII）。3-氟苯丙氨酸（V）可通过（IV）或（VII）的酸性水解获得，而异丙基-3氟苯丙氨酸盐（VI）可通过（V）的酯化或与异丙醇-12 NHCl加热（IV）来分离在回流下。