[(7R,9S)-((E)-9-Propenyl)-1,4-dioxa-8-aza-spiro[4.5]dec-7-yl]-acetic acid methyl ester | 721916-90-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(7R,9S)-((E)-9-Propenyl)-1,4-dioxa-8-aza-spiro[4.5]dec-7-yl]-acetic acid methyl ester
• CAS: 721916-90-1
• 化学式: C₁₃H₂₁NO₄
• 分子量: 255.314
• InChiKey: PCDAXPAHVYTFGB-YHROSDCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.99
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  [(7R,9S)-((E)-9-Propenyl)-1,4-dioxa-8-aza-spiro[4.5]dec-7-yl]-acetic acid methyl ester 在 ethandithiol 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以339 mg的产率得到(-)-(2S,6S)-1-aza-6-(methoxycarbonyl)methyl-2-prop-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：

  ethyl (2E)-4-(2-methyl-1,3-dioxolan-2-yl)but-2-enoate 在 palladium dihydroxide 正丁基锂 、 ammonium formate 、 magnesium sulfate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 [(7R,9S)-((E)-9-Propenyl)-1,4-dioxa-8-aza-spiro[4.5]dec-7-yl]-acetic acid methyl ester
  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