(Z)-2-benzyloxycarbonylamino-5-phenylpent-2-enoic acid (-)-8-phenylmenthyl ester | 917603-63-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (Z)-2-benzyloxycarbonylamino-5-phenylpent-2-enoic acid (-)-8-phenylmenthyl ester
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (Z)-5-phenyl-2-(phenylmethoxycarbonylamino)pent-2-enoate
• CAS: 917603-63-5
• 化学式: C₃₅H₄₁NO₄
• 分子量: 539.715
• InChiKey: KZKNJHAEDULCAX-QXBIUKFSSA-N

物化性质

• 沸点：
  657.0±55.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-2-benzyloxycarbonylamino-5-phenylpent-2-enoic acid (-)-8-phenylmenthyl ester 、 碘甲烷 在 正丁基锂 、 二异丙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 7.33h， 生成 (2S,3E)-2-benzyloxycarbonylamino-2-methyl-5-phenylpent-3-enoic acid (-)-8-phenylmenthyl ester 、 (2R,3E)-2-benzyloxycarbonylamino-2-methyl-5-phenylpent-3-enoic acid (-)-8-phenylmenthyl ester
  参考文献：
  名称：

  Efficient Asymmetric Synthesis of Quaternary (E)-Vinylglycines by Deconjugative Alkylation of Dehydroamino Acids

  摘要：

  A two-step protocol for the asymmetric synthesis of protected quaternary (E)-vinylglycines from simple aldehydes is reported. The key step is a regiocontrolled deconjugative asymmetric alkylation of dehydroamino acids, giving the targets as single geometric isomers with high diastereoselectivity (92-96% de). The products can be converted to valuable quaternary beta-amino alcohols by chemoselective reduction.

  DOI：

  10.1021/ol062162r
• 作为产物：
  描述：

  2-Benzyloxycarbonylamino-2-(diethoxyphosphinyl)-acetic acid 在 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 120.5h， 生成 (Z)-2-benzyloxycarbonylamino-5-phenylpent-2-enoic acid (-)-8-phenylmenthyl ester
  参考文献：
  名称：

  Efficient Asymmetric Synthesis of Quaternary (E)-Vinylglycines by Deconjugative Alkylation of Dehydroamino Acids

  摘要：

  A two-step protocol for the asymmetric synthesis of protected quaternary (E)-vinylglycines from simple aldehydes is reported. The key step is a regiocontrolled deconjugative asymmetric alkylation of dehydroamino acids, giving the targets as single geometric isomers with high diastereoselectivity (92-96% de). The products can be converted to valuable quaternary beta-amino alcohols by chemoselective reduction.

  DOI：

  10.1021/ol062162r

文献信息

• Efficient Asymmetric Synthesis of Quaternary (<i>E</i>)-Vinylglycines by Deconjugative Alkylation of Dehydroamino Acids
  作者：Matthew C. Jones、Stephen P. Marsden、Dulce M. Muñoz Subtil

  DOI：10.1021/ol062162r

  日期：2006.11.1

  A two-step protocol for the asymmetric synthesis of protected quaternary (E)-vinylglycines from simple aldehydes is reported. The key step is a regiocontrolled deconjugative asymmetric alkylation of dehydroamino acids, giving the targets as single geometric isomers with high diastereoselectivity (92-96% de). The products can be converted to valuable quaternary beta-amino alcohols by chemoselective reduction.