<1R-<1α(R*),3aβ,4α(1R*,5R*),7aα>>-1-<1,5-dimethyl-5-<(trimethylsilyl)oxy>hexyl>octahydro-7a-methyl-4-<(2-methylenebicyclo<3.1.0>hexan-1-yl)ethynyl>-1H-inden-4-ol | 172376-14-6

• 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: <1R-<1α(R*),3aβ,4α(1R*,5R*),7aα>>-1-<1,5-dimethyl-5-<(trimethylsilyl)oxy>hexyl>octahydro-7a-methyl-4-<(2-methylenebicyclo<3.1.0>hexan-1-yl)ethynyl>-1H-inden-4-ol
• 英文别名: (1R,3aR,4S,7aR)-7a-methyl-4-[2-[(1R,5R)-2-methylidene-1-bicyclo[3.1.0]hexanyl]ethynyl]-1-[(2R)-6-methyl-6-trimethylsilyloxyheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ol
• CAS: 172376-14-6
• 化学式: C₃₀H₅₀O₂Si
• 分子量: 470.811
• InChiKey: BJRDRTHWKOJMRM-FUKUPJPLSA-N

物化性质

• 沸点：
  512.8±43.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.73
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  <1R-<1α(R*),3aβ,4α(1R*,5R*),7aα>>-1-<1,5-dimethyl-5-<(trimethylsilyl)oxy>hexyl>octahydro-7a-methyl-4-<(2-methylenebicyclo<3.1.0>hexan-1-yl)ethynyl>-1H-inden-4-ol 在 咪唑 、 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 selenium(IV) oxide 、 甲基叔丁基醚 、 乙酸9-蒽基酯 、 四丁基氟化铵 、 sodium methylate 、 三乙基硼氢化锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 46.0h， 生成 骨化三醇
  参考文献：
  名称：

  Convergent Synthesis of Vitamin D₃ Metabolites. Control of the Stereoselectivity in Samarium-Induced Cyclopropanations of Cyclopentenes

  摘要：

  The 25-hydroxy and 1 alpha,25-dihydroxy vitamin D-3 metabolites are obtained by solvolytic rearrangements of the 1-desoxy and 1 alpha-hydroxy cyclopropyl vinylogous alcohols 31 and 29, respectively, with simultaneous formation of the vitamin D structural triene and the 3-hydroxy function. Two complementary methods have been employed to direct the stereoselectivity ofthe samarium induced olefin cyclopropanations which ultimately lead to key chiral ring A precursors. One protocol uses the two stereogenic centers of the (R,R)-B,S-butanediol ketal moiety of 8, while the other method uses the allylic hydroxyl group of(R)-16.

  DOI：

  10.1021/jo951229d
• 作为产物：
  描述：

  (R)-2-<(trimethylsilyl)ethynyl>-2-cyclopenten-1-ol 在 三氢化钐 、 正丁基锂 、 potassium tert-butylate 、 pyridinium chlorochromate 、 mercury dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.58h， 生成 <1R-<1α(R*),3aβ,4α(1R*,5R*),7aα>>-1-<1,5-dimethyl-5-<(trimethylsilyl)oxy>hexyl>octahydro-7a-methyl-4-<(2-methylenebicyclo<3.1.0>hexan-1-yl)ethynyl>-1H-inden-4-ol
  参考文献：
  名称：

  Convergent Synthesis of Vitamin D₃ Metabolites. Control of the Stereoselectivity in Samarium-Induced Cyclopropanations of Cyclopentenes

  摘要：

  The 25-hydroxy and 1 alpha,25-dihydroxy vitamin D-3 metabolites are obtained by solvolytic rearrangements of the 1-desoxy and 1 alpha-hydroxy cyclopropyl vinylogous alcohols 31 and 29, respectively, with simultaneous formation of the vitamin D structural triene and the 3-hydroxy function. Two complementary methods have been employed to direct the stereoselectivity ofthe samarium induced olefin cyclopropanations which ultimately lead to key chiral ring A precursors. One protocol uses the two stereogenic centers of the (R,R)-B,S-butanediol ketal moiety of 8, while the other method uses the allylic hydroxyl group of(R)-16.

  DOI：

  10.1021/jo951229d