((1R,2R,4S)-3,3-Dimethoxy-bicyclo[2.2.1]hept-5-en-2-yl)-methanol | 176979-78-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((1R,2R,4S)-3,3-Dimethoxy-bicyclo[2.2.1]hept-5-en-2-yl)-methanol
• 英文别名: [(1R,2R,4S)-3,3-dimethoxy-2-bicyclo[2.2.1]hept-5-enyl]methanol
• CAS: 176979-78-5
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: NSTACLQUVCIOPZ-YIZRAAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ((1R,2R,4S)-3,3-Dimethoxy-bicyclo[2.2.1]hept-5-en-2-yl)-methanol 在 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 氯化铵 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.33h， 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,SS)-menthyl 3-endo-(2-pyridylsulphinyl)bicyclo-<2.2.1>hept-5-ene-2-endo-carboxylate 在 2,6-二甲基吡啶 、 lithium aluminium tetrahydride 、 对甲苯磺酸 、 三氟乙酸酐 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 ((1R,2R,4S)-3,3-Dimethoxy-bicyclo[2.2.1]hept-5-en-2-yl)-methanol
  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.