(-)-2-hydroxy-2-phenyl-malonamic acid menthyl ester | 874016-51-0

• 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: (-)-2-hydroxy-2-phenyl-malonamic acid menthyl ester
• 英文别名: [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (2S)-3-amino-2-hydroxy-3-oxo-2-phenylpropanoate
• CAS: 874016-51-0
• 化学式: C₁₉H₂₇NO₄
• 分子量: 333.428
• InChiKey: BCRPPRSJHMQWPY-DEWZPKMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-2-hydroxy-2-phenyl-malonamic acid menthyl ester 在 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 2,3-dihydroxy-N-isopropyl-2-phenyl-propionamide
  参考文献：
  名称：

  Oxidation of chiral α-phenylacetate derivatives: formation of dimers with contiguous quaternary stereocenters versus tertiary alcohols

  摘要：

  The menthol esters of alpha-phenylacetate derivatives undergo diastereoselective oxidative dimerizations (alpha-cyano) in the presence of oxidants, and nitrosylation (alpha-amido) in the presence of CAN to form products containing adjacent functionalized quaternary stereocenters and tertiary alcohols, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.008
• 作为产物：
  描述：

  2-nitrooxy-2-phenyl-malonamic acid menthyl ester 在 镍 氢气 作用下， 以 甲醇 、 水 为溶剂， 以40%的产率得到(-)-2-hydroxy-2-phenyl-malonamic acid menthyl ester
  参考文献：
  名称：

  Oxidation of chiral α-phenylacetate derivatives: formation of dimers with contiguous quaternary stereocenters versus tertiary alcohols

  摘要：

  The menthol esters of alpha-phenylacetate derivatives undergo diastereoselective oxidative dimerizations (alpha-cyano) in the presence of oxidants, and nitrosylation (alpha-amido) in the presence of CAN to form products containing adjacent functionalized quaternary stereocenters and tertiary alcohols, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.008

文献信息

• Oxidation of chiral α-phenylacetate derivatives: formation of dimers with contiguous quaternary stereocenters versus tertiary alcohols
  作者：Marisa C. Kozlowski、Evan S. DiVirgilio、Krishnan Malolanarasimhan、Carol A. Mulrooney

  DOI：10.1016/j.tetasy.2005.10.008

  日期：2005.10

  The menthol esters of alpha-phenylacetate derivatives undergo diastereoselective oxidative dimerizations (alpha-cyano) in the presence of oxidants, and nitrosylation (alpha-amido) in the presence of CAN to form products containing adjacent functionalized quaternary stereocenters and tertiary alcohols, respectively. (c) 2005 Elsevier Ltd. All rights reserved.