methyl (1'R,3S)-5,5-ethylenedioxy-3-(1'-methylbenzylamino)-hexanoate | 721916-85-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (1'R,3S)-5,5-ethylenedioxy-3-(1'-methylbenzylamino)-hexanoate
• 英文别名: methyl (3S)-4-(2-methyl-1,3-dioxolan-2-yl)-3-[[(1R)-1-phenylethyl]amino]butanoate
• CAS: 721916-85-4
• 化学式: C₁₇H₂₅NO₄
• 分子量: 307.39
• InChiKey: UJBVIUIXJIAEFT-UKRRQHHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (1'R,3S)-5,5-ethylenedioxy-3-(1'-methylbenzylamino)-hexanoate 在 palladium on activated charcoal ethandithiol 、 三氟化硼乙醚 、 ammonium formate 、 镍 、 magnesium sulfate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 methyl (2S,6S)-2-[(methoxycarbonyl)methyl]-6-pentylpiperidine
  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：

  (2-methyl-[1,3]dioxolan-2-yl)-acetic acid 在 sodium tetrahydroborate 、 草酰氯 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 33.0h， 生成 methyl (1'R,3S)-5,5-ethylenedioxy-3-(1'-methylbenzylamino)-hexanoate
  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