(5S)-5-(acetoxymethyl)tetrahydropyran-2-one | 255370-22-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (5S)-5-(acetoxymethyl)tetrahydropyran-2-one
• 英文别名: [(3S)-6-oxooxan-3-yl]methyl acetate
• CAS: 255370-22-0
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: WOESWKVORGGXHG-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S)-5-(acetoxymethyl)tetrahydropyran-2-one 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 (4S)-N-[2-(N-Boc-indol-3-yl)ethyl]-4-acetoxymethyl-5-mesyloxypentanamide
  参考文献：
  名称：

  Formal enantioselective synthesis of tacamonine starting from asymmetrized 2-substituted propane-1,3-diols

  摘要：

  2-Substituted propanediols monoacetates, derived from enzymatic asymmetrization of the corresponding diols, have been obtained in high yields and enantiomeric excesses by using lipases and vinyl acetate as both solvent and acylating agent. These chiral building blocks have been transformed into the advanced intermediate 3, useful for the enantioselective synthesis of tacamane alkaloids. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00434-6
• 作为产物：
  描述：

  (2R)-2-(acetoxymethyl)hex-5-en-1-ol 在 Celite 、 臭氧 、 silver carbonate 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 8.08h， 生成 (5S)-5-(acetoxymethyl)tetrahydropyran-2-one
  参考文献：
  名称：

  Formal enantioselective synthesis of tacamonine starting from asymmetrized 2-substituted propane-1,3-diols

  摘要：

  2-Substituted propanediols monoacetates, derived from enzymatic asymmetrization of the corresponding diols, have been obtained in high yields and enantiomeric excesses by using lipases and vinyl acetate as both solvent and acylating agent. These chiral building blocks have been transformed into the advanced intermediate 3, useful for the enantioselective synthesis of tacamane alkaloids. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00434-6

文献信息

• Formal enantioselective synthesis of tacamonine starting from asymmetrized 2-substituted propane-1,3-diols
  作者：Bruno Danieli、Giordano Lesma、Silvia Macecchini、Daniele Passarella、Alessandra Silvani

  DOI：10.1016/s0957-4166(99)00434-6

  日期：1999.10

  2-Substituted propanediols monoacetates, derived from enzymatic asymmetrization of the corresponding diols, have been obtained in high yields and enantiomeric excesses by using lipases and vinyl acetate as both solvent and acylating agent. These chiral building blocks have been transformed into the advanced intermediate 3, useful for the enantioselective synthesis of tacamane alkaloids. (C) 1999 Elsevier Science Ltd. All rights reserved.