(3S,5S,6R,7S,8S,9S,10R,13R,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-7-phenyl-hexadecahydro-20-oxa-cyclopropa[5,6]cyclopenta[a]phenanthren-7-ol | 189103-26-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (3S,5S,6R,7S,8S,9S,10R,13R,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-7-phenyl-hexadecahydro-20-oxa-cyclopropa[5,6]cyclopenta[a]phenanthren-7-ol
• 英文别名: (1S,2R,5S,7S,9R,10S,11S,12S,15R,16R)-5-[tert-butyl(dimethyl)silyl]oxy-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-10-phenyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-10-ol
• CAS: 189103-26-2
• 化学式: C₃₉H₆₄O₃Si
• 分子量: 609.021
• InChiKey: DIMQIYWYNYWUKU-JZGFJXACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.13
• 重原子数：
  43
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,5S,6R,7S,8S,9S,10R,13R,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-7-phenyl-hexadecahydro-20-oxa-cyclopropa[5,6]cyclopenta[a]phenanthren-7-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到5β,6β-epoxy-7α-phenylcholestane-3β,7β-diol
  参考文献：
  名称：

  Unusual oxidation reactions of 7α-methyl- and 7α-phenylcholest-5-ene-3β,7β-diol

  摘要：

  Ozonation of 7 alpha-methyl(or 7 alpha-phenyl) cholest-5-ene-3 beta,7 beta-diol 3-TBDMS ether afforded the corresponding 5 beta,6 beta-epoxy derivatives. The same product was formed by MCPBA oxidation. The reaction of 7 alpha-phenylcholest-5-ene- 3 beta,7 beta-diol with CrO3 yielded 3,7-dioxo-6,7-seco-7-phenylcholest-4-ene-5-carboxaldehyde. An analogous B-seco aldehyde was obtained from 7 alpha-methylcholest-5-ene-3 beta,7 beta-diol in addition to 7-methylcholesta-4,6-dien-3-one. Jones oxidation of 7 alpha-phenylcholest-5-ene-3 3 beta,7 beta-diol or B-seco-aldehyde gave 3,7-dioxo-6,7-seco-7-phenylcholest-4-en-6-oic acid isolated as its methyl ester upon treatment with diazomethane.

  DOI：

  10.1007/bf00807796
• 作为产物：
  描述：

  (3S,7R,8S,9S,10R,13R,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-7-phenyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol 在 臭氧 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 以59.4%的产率得到(3S,5S,6R,7S,8S,9S,10R,13R,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-7-phenyl-hexadecahydro-20-oxa-cyclopropa[5,6]cyclopenta[a]phenanthren-7-ol
  参考文献：
  名称：

  Unusual oxidation reactions of 7α-methyl- and 7α-phenylcholest-5-ene-3β,7β-diol

  摘要：

  Ozonation of 7 alpha-methyl(or 7 alpha-phenyl) cholest-5-ene-3 beta,7 beta-diol 3-TBDMS ether afforded the corresponding 5 beta,6 beta-epoxy derivatives. The same product was formed by MCPBA oxidation. The reaction of 7 alpha-phenylcholest-5-ene- 3 beta,7 beta-diol with CrO3 yielded 3,7-dioxo-6,7-seco-7-phenylcholest-4-ene-5-carboxaldehyde. An analogous B-seco aldehyde was obtained from 7 alpha-methylcholest-5-ene-3 beta,7 beta-diol in addition to 7-methylcholesta-4,6-dien-3-one. Jones oxidation of 7 alpha-phenylcholest-5-ene-3 3 beta,7 beta-diol or B-seco-aldehyde gave 3,7-dioxo-6,7-seco-7-phenylcholest-4-en-6-oic acid isolated as its methyl ester upon treatment with diazomethane.

  DOI：

  10.1007/bf00807796