methyl 2-(2'-dimethoxyphosphoryl-1'-methyl-2'-phenylcyclopropyl-1'-methylimino)-3-phenylpropanoate | 1292323-11-5

• 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: methyl 2-(2'-dimethoxyphosphoryl-1'-methyl-2'-phenylcyclopropyl-1'-methylimino)-3-phenylpropanoate
• 英文别名: methyl (2S)-2-[[2-[dimethoxy(oxido)phosphaniumyl]-1-methyl-2-phenylcyclopropyl]methylideneamino]-3-phenylpropanoate
• CAS: 1292323-11-5
• 化学式: C₂₃H₂₈NO₅P
• 分子量: 429.453
• InChiKey: RERFFYADURQUER-RBKXMNCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  80.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-(2'-dimethoxyphosphoryl-1'-methyl-2'-phenylcyclopropyl-1'-methylimino)-3-phenylpropanoate 在 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 (2S)-methyl 2-(2'-dimethoxyphosphoryl-1'-methyl-2'-phenylcyclopropyl-1'-methylamino)-3-phenylpropanoate 、 (2S)-methyl 2-(2'-dimethoxyphosphoryl-1'-methyl-2'-phenylcyclopropyl-1'-methylamino)-3-phenylpropanoate
  参考文献：
  名称：

  (2-Formyl-1-phenylcyclopropyl)phosphonates as building blocks for (2-aminomethyl-cyclopropyl)phosphonates

  摘要：

  A diastereomeric mixture of dimethyl (2-formyl-2-methyl-1-phenylcyclopropyl)phosphonate ((Z)-6, (E)-6) was obtained by thermally induced cyclopropanation of a-methylacrolein with alpha-diazobenzylphosphonate 5. Application of proline or proline-derived organocatalysts accelerated the reaction, but had a minor effect on the Z/E ratio of 6. By reaction with benzylamine or methyl esters of glycine, (S)-alanine, and (S)-phenylalanine, the Z/E-mixture of 6 was converted into cyclopropylaldimines, which after reduction gave the corresponding N-substituted (2-aminomethyl-cyclopropyl)phosphonates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.068
• 作为产物：
  描述：

  dimethyl (2-formyl-2-methyl-1-phenylcyclopropyl)phosphonate 、 L-苯丙氨酸甲酯 在 sodium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以94%的产率得到methyl 2-(2'-dimethoxyphosphoryl-1'-methyl-2'-phenylcyclopropyl-1'-methylimino)-3-phenylpropanoate
  参考文献：
  名称：

  (2-Formyl-1-phenylcyclopropyl)phosphonates as building blocks for (2-aminomethyl-cyclopropyl)phosphonates

  摘要：

  A diastereomeric mixture of dimethyl (2-formyl-2-methyl-1-phenylcyclopropyl)phosphonate ((Z)-6, (E)-6) was obtained by thermally induced cyclopropanation of a-methylacrolein with alpha-diazobenzylphosphonate 5. Application of proline or proline-derived organocatalysts accelerated the reaction, but had a minor effect on the Z/E ratio of 6. By reaction with benzylamine or methyl esters of glycine, (S)-alanine, and (S)-phenylalanine, the Z/E-mixture of 6 was converted into cyclopropylaldimines, which after reduction gave the corresponding N-substituted (2-aminomethyl-cyclopropyl)phosphonates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.068

文献信息

• (2-Formyl-1-phenylcyclopropyl)phosphonates as building blocks for (2-aminomethyl-cyclopropyl)phosphonates
  作者：Ahmed El-Gokha、Gerhard Maas

  DOI：10.1016/j.tet.2011.02.068

  日期：2011.4

  A diastereomeric mixture of dimethyl (2-formyl-2-methyl-1-phenylcyclopropyl)phosphonate ((Z)-6, (E)-6) was obtained by thermally induced cyclopropanation of a-methylacrolein with alpha-diazobenzylphosphonate 5. Application of proline or proline-derived organocatalysts accelerated the reaction, but had a minor effect on the Z/E ratio of 6. By reaction with benzylamine or methyl esters of glycine, (S)-alanine, and (S)-phenylalanine, the Z/E-mixture of 6 was converted into cyclopropylaldimines, which after reduction gave the corresponding N-substituted (2-aminomethyl-cyclopropyl)phosphonates. (C) 2011 Elsevier Ltd. All rights reserved.