[(1S,2R,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-bicyclo[2.2.1]hept-5-en-2-yl]-acetic acid ethyl ester | 176979-80-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(1S,2R,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-bicyclo[2.2.1]hept-5-en-2-yl]-acetic acid ethyl ester
• 英文别名: ethyl 2-[(1S,2R,3R,4R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-hydroxy-2-bicyclo[2.2.1]hept-5-enyl]acetate
• CAS: 176979-80-9
• 化学式: C₁₈H₃₂O₄Si
• 分子量: 340.535
• InChiKey: BTYAULXVUBKSRH-JTOWHCCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1S,2R,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-bicyclo[2.2.1]hept-5-en-2-yl]-acetic acid ethyl ester 在 吡啶 、 氯化亚砜 作用下， 反应 0.25h， 生成 [(1S,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-bicyclo[2.2.1]hept-5-en-(2Z)-ylidene]-acetic acid ethyl ester 、 [(1S,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-bicyclo[2.2.1]hept-5-en-(2E)-ylidene]-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 咪唑 、 2,6-二甲基吡啶 、 盐酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氯化铵 、 对甲苯磺酸 、 三氟乙酸酐 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 10.33h， 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