(1'R,3R)-ethyl 3-(N-benzyl-N-1'-methylbenzylamino)-5,5-ethylenedioxyhexanoate | 721916-88-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1'R,3R)-ethyl 3-(N-benzyl-N-1'-methylbenzylamino)-5,5-ethylenedioxyhexanoate
• CAS: 721916-88-7
• 化学式: C₂₅H₃₃NO₄
• 分子量: 411.541
• InChiKey: AODZCBLNOVGLQZ-OFNKIYASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  30.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  48.0
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1'R,3R)-ethyl 3-(N-benzyl-N-1'-methylbenzylamino)-5,5-ethylenedioxyhexanoate 在 palladium dihydroxide ethandithiol 、 三氟化硼乙醚 、 ammonium formate 、 magnesium sulfate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 (+)-(2R,6R)-1-aza-6-(methoxycarbonyl)methyl-2-pent-1''-enyl-1',3'-dithiaspiro[5,4]decane
  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：

  (R)-(+)-N-苄基-1-苯乙胺 、 ethyl (2E)-4-(2-methyl-1,3-dioxolan-2-yl)but-2-enoate 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 生成 (1'R,3S)-ethyl 3-(N-benzyl-N-1'-methylbenzylamino)-5,5-ethylenedioxyhexanoate 、 (1'R,3R)-ethyl 3-(N-benzyl-N-1'-methylbenzylamino)-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