(1R,5S,8S)-8-(2,2-dimethoxyethyl)-8-methyl-2-methylen-6-oxabicyclo[3.2.1]octan-7-one | 1039740-22-1

• 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: (1R,5S,8S)-8-(2,2-dimethoxyethyl)-8-methyl-2-methylen-6-oxabicyclo[3.2.1]octan-7-one
• 英文别名: (1R,5S,8S)-8-(2,2-dimethoxyethyl)-8-methyl-2-methylidene-6-oxabicyclo[3.2.1]octan-7-one
• CAS: 1039740-22-1
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: WOFMEHGSNLNSGM-XHVZSJERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,5S,8S)-8-(2,2-dimethoxyethyl)-8-methyl-2-methylen-6-oxabicyclo[3.2.1]octan-7-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以95%的产率得到(1S,2S,3R)-2-(2,2-二甲氧基乙基)-3-(羟甲基)-2-甲基-4-亚甲基环己醇
  参考文献：
  名称：

  Highly Efficient Stereocontrolled Synthesis of Danishefsky’s Taxol CD Ring Key Intermediate

  摘要：

  Danishefsky's taxol CD ring key intermediate is synthesized in 15 steps and 11.4% overall yield from a readily available starting material. Absolute stereochemistry of the starting material and stereocontrolled steps determine the absolute configuration of the five requisite contiguous stereocenters.

  DOI：

  10.1021/jo800913x
• 作为产物：
  描述：

  甲醇 、 (1R,5S,8S)-8-(2-methoxyvinyl)-8-methyl-2-methylen-6-oxabicyclo[3.2.1]octan-7-one 在 camphor-10-sulfonic acid 作用下， 反应 2.0h， 以93%的产率得到(1R,5S,8S)-8-(2,2-dimethoxyethyl)-8-methyl-2-methylen-6-oxabicyclo[3.2.1]octan-7-one
  参考文献：
  名称：

  Highly Efficient Stereocontrolled Synthesis of Danishefsky’s Taxol CD Ring Key Intermediate

  摘要：

  Danishefsky's taxol CD ring key intermediate is synthesized in 15 steps and 11.4% overall yield from a readily available starting material. Absolute stereochemistry of the starting material and stereocontrolled steps determine the absolute configuration of the five requisite contiguous stereocenters.

  DOI：

  10.1021/jo800913x

文献信息

• Highly Efficient Stereocontrolled Synthesis of Danishefsky’s Taxol CD Ring Key Intermediate
  作者：Paul Brémond、Gérard Audran、Honoré Monti

  DOI：10.1021/jo800913x

  日期：2008.8.1

  Danishefsky's taxol CD ring key intermediate is synthesized in 15 steps and 11.4% overall yield from a readily available starting material. Absolute stereochemistry of the starting material and stereocontrolled steps determine the absolute configuration of the five requisite contiguous stereocenters.