(1R,5S,8S)-8-methyl-2-methylen-7-oxo-6-oxabicyclo[3.2.1]octane-8-carbaldehyde | 1039740-18-5

• 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-methyl-2-methylen-7-oxo-6-oxabicyclo[3.2.1]octane-8-carbaldehyde
• 英文别名: (1R,5S,8S)-8-methyl-2-methylidene-7-oxo-6-oxabicyclo[3.2.1]octane-8-carbaldehyde
• CAS: 1039740-18-5
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: QRKWCXJSYMZAGA-OYNCUSHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,5S,8S)-8-methyl-2-methylen-7-oxo-6-oxabicyclo[3.2.1]octane-8-carbaldehyde 、 甲氧基甲基三苯基氯化膦 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 (1R,5S,8S)-8-(2-methoxyvinyl)-8-methyl-2-methylen-6-oxabicyclo[3.2.1]octan-7-one 、 (1R,5S,8S)-8-(2-methoxyvinyl)-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
• 作为产物：
  描述：

  (1R,5S,8S)-8-methyl-2-methylene-8-vinyl-6-oxabicyclo[3.2.1]octan-7-one 在 sodium periodate 、 四氧化锇 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以85%的产率得到(1R,5S,8S)-8-methyl-2-methylen-7-oxo-6-oxabicyclo[3.2.1]octane-8-carbaldehyde
  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.