methyl 5,5-ethylenedioxy-3-((1'R)-1'-methylbenzylamino)-hex-2-enoate | 721916-83-2

• 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: methyl 5,5-ethylenedioxy-3-((1'R)-1'-methylbenzylamino)-hex-2-enoate
• CAS: 721916-83-2
• 化学式: C₁₇H₂₃NO₄
• 分子量: 305.374
• InChiKey: JGOJQGVOCQTXPW-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  56.79
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 5,5-ethylenedioxy-3-((1'R)-1'-methylbenzylamino)-hex-2-enoate 在 palladium on activated charcoal sodium tetrahydroborate 、 ammonium formate 、 溶剂黄146 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 9.0h， 生成 (+)-(3S)-methyl 3-amino-5,5-ethylenedioxyhexanoate
  参考文献：
  名称：

  A β,β′-ketoaminoester as a valuable tool for the asymmetric construction of substituted homopipecolic esters: application to a formal synthesis of (+)-Calvine

  摘要：

  A highly diastereoselective 1,4-addition involving Davies' lithium amide is employed as the key reaction to prepare, in five steps from ethyl acetoacetate, an enantiomerically pure keto protected beta,beta'-ketoaminoester. This latter was reacted with aldehydes in an intramolecular Mannich process and furnished a direct and stereoselective access to substituted homopipecolates. The validity of this approach was achieved through a new formal asymmetric synthesis of alkaloid (+)-Calvine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.008
• 作为产物：
  描述：

  3-oxobutanoyl chloride ethylene ketal 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 26.0h， 生成 methyl 5,5-ethylenedioxy-3-((1'R)-1'-methylbenzylamino)-hex-2-enoate
  参考文献：
  名称：

  A β,β′-ketoaminoester as a valuable tool for the asymmetric construction of substituted homopipecolic esters: application to a formal synthesis of (+)-Calvine

  摘要：

  A highly diastereoselective 1,4-addition involving Davies' lithium amide is employed as the key reaction to prepare, in five steps from ethyl acetoacetate, an enantiomerically pure keto protected beta,beta'-ketoaminoester. This latter was reacted with aldehydes in an intramolecular Mannich process and furnished a direct and stereoselective access to substituted homopipecolates. The validity of this approach was achieved through a new formal asymmetric synthesis of alkaloid (+)-Calvine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.008