(1S,3R,4R)-3-Hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-one | 176979-79-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R,4R)-3-Hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-one
• 英文别名: (1S,3R,4R)-3-(hydroxymethyl)bicyclo[2.2.1]hept-5-en-2-one
• CAS: 176979-79-6
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: NFOWLWUQKPUSLW-XVMARJQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R)-3-Hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-one 在 咪唑 、 4-二甲氨基吡啶 、 氯化铵 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 [(1S,2R,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-bicyclo[2.2.1]hept-5-en-2-yl]-acetic acid ethyl ester
  参考文献：
  名称：

  Enantioselective Total Synthesis of cis-Trikentrin B

  摘要：

  Natural cis-trikentrin B was synthesized enantioselectively using, as key steps, an intramolecular Diels-Alder reaction of an allenic dienamide followed by aromatization to construct an indole ring and cleavage of bicyclo[2.2.1]heptene to launch a cis-dimethylcyclopentane ring. Diels-Alder adducts 9 and 10 were elaborated to provide allenic dienamide 25, and its intramolecular Diels-Alder reaction proceeded smoothly. Aromatization to an indole ring and stereoselective cleavage of the bicyclo[2.2.1]heptene ring were performed successfully. Introduction of an (E)-butenyl group via addition of propylmagnesium bromide and subsequent anti elimination of water gave natural cis-trikentrin B.

  DOI：

  10.1021/jo951767q
• 作为产物：
  描述：

  ((1R,2R,4S)-3,3-Dimethoxy-bicyclo[2.2.1]hept-5-en-2-yl)-methanol 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以95%的产率得到(1S,3R,4R)-3-Hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-one
  参考文献：
  名称：

  Enantioselective Total Synthesis of cis-Trikentrin B

  摘要：

  Natural cis-trikentrin B was synthesized enantioselectively using, as key steps, an intramolecular Diels-Alder reaction of an allenic dienamide followed by aromatization to construct an indole ring and cleavage of bicyclo[2.2.1]heptene to launch a cis-dimethylcyclopentane ring. Diels-Alder adducts 9 and 10 were elaborated to provide allenic dienamide 25, and its intramolecular Diels-Alder reaction proceeded smoothly. Aromatization to an indole ring and stereoselective cleavage of the bicyclo[2.2.1]heptene ring were performed successfully. Introduction of an (E)-butenyl group via addition of propylmagnesium bromide and subsequent anti elimination of water gave natural cis-trikentrin B.

  DOI：

  10.1021/jo951767q

文献信息

• Enantioselective Total Synthesis of <i>cis</i>-Trikentrin B
  作者：Mase Lee、Izumi Ikeda、Tsuyoshi Kawabe、Sayaka Mori、Ken Kanematsu

  DOI：10.1021/jo951767q

  日期：1996.1.1

  Natural cis-trikentrin B was synthesized enantioselectively using, as key steps, an intramolecular Diels-Alder reaction of an allenic dienamide followed by aromatization to construct an indole ring and cleavage of bicyclo[2.2.1]heptene to launch a cis-dimethylcyclopentane ring. Diels-Alder adducts 9 and 10 were elaborated to provide allenic dienamide 25, and its intramolecular Diels-Alder reaction proceeded smoothly. Aromatization to an indole ring and stereoselective cleavage of the bicyclo[2.2.1]heptene ring were performed successfully. Introduction of an (E)-butenyl group via addition of propylmagnesium bromide and subsequent anti elimination of water gave natural cis-trikentrin B.