[(2R,3S,5R,8S,9S,10R,13R,14S,17R)-3-Acetoxy-17-((R)-1,5-dimethyl-hexyl)-5-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-2-yl]-acetic acid | 157920-52-0

• 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: [(2R,3S,5R,8S,9S,10R,13R,14S,17R)-3-Acetoxy-17-((R)-1,5-dimethyl-hexyl)-5-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-2-yl]-acetic acid
• 英文别名: 2-[(2R,3S,5R,8S,9S,10R,13R,14S,17R)-3-acetyloxy-5-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-2-yl]acetic acid
• CAS: 157920-52-0
• 化学式: C₃₁H₅₂O₅
• 分子量: 504.751
• InChiKey: SARNUMXTJKBSCW-DAFIDGJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R,8S,9S,10R,13R,14S,17R)-3-Acetoxy-17-((R)-1,5-dimethyl-hexyl)-5-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-2-yl]-acetic acid 在 氢氧化钾 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 24.67h， 生成 (2α,3α)H-dihydro-2'(3'H)-oxofuro<4'5':2,3>cholestan-5α-ol
  参考文献：
  名称：

  Fragmentation of Alkoxy Radicals: Tandem .beta.-Fragmentation-Cycloperoxyiodination Reaction

  摘要：

  The steroidal alcohols 2-cholesten-5 alpha-ol (3), 3-phenyl-2-cholesten-5 alpha-ol (4), and 3 alpha H-2'-oxofuro-[2,3]cholestan-5 alpha-ol (5) were prepared in order to test a new tandem beta-fragmentation-cycloperoxyiodination reaction. The alkoxy radicals generated by irradiation of these alcohols with visible light in the presence of (diacetoxyiodo)benzene, I-2, and molecular oxygen undergo a beta-fragmentation reaction with subsequent peroxidation of the C-radical formed. This peroxy radical is added to conveniently positioned double bonds to give 10-membered cyclic ketones possessing a 1,2-dioxolane group.

  DOI：

  10.1021/jo00095a012
• 作为产物：
  描述：

  2β-(2'-propenyl)cholestane-3α,5α-diol 3-acetate 在 ruthenium trichloride 、 过碘酸 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 1.0h， 生成 [(2R,3S,5R,8S,9S,10R,13R,14S,17R)-3-Acetoxy-17-((R)-1,5-dimethyl-hexyl)-5-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-2-yl]-acetic acid
  参考文献：
  名称：

  Fragmentation of Alkoxy Radicals: Tandem .beta.-Fragmentation-Cycloperoxyiodination Reaction

  摘要：

  The steroidal alcohols 2-cholesten-5 alpha-ol (3), 3-phenyl-2-cholesten-5 alpha-ol (4), and 3 alpha H-2'-oxofuro-[2,3]cholestan-5 alpha-ol (5) were prepared in order to test a new tandem beta-fragmentation-cycloperoxyiodination reaction. The alkoxy radicals generated by irradiation of these alcohols with visible light in the presence of (diacetoxyiodo)benzene, I-2, and molecular oxygen undergo a beta-fragmentation reaction with subsequent peroxidation of the C-radical formed. This peroxy radical is added to conveniently positioned double bonds to give 10-membered cyclic ketones possessing a 1,2-dioxolane group.

  DOI：

  10.1021/jo00095a012

文献信息

• Boto Alicia, Betancor Carmen, Prange Thierry, Suarez Ernesto, J. Org. Chem, 59 (1994) N 16, S 4393-4401
  作者：Boto Alicia, Betancor Carmen, Prange Thierry, Suarez Ernesto

  DOI：——

  日期：——
• Fragmentation of Alkoxy Radicals: Tandem .beta.-Fragmentation-Cycloperoxyiodination Reaction
  作者：Alicia Boto、Carmen Betancor、Thierry Prange、Ernesto Suarez

  DOI：10.1021/jo00095a012

  日期：1994.8

  The steroidal alcohols 2-cholesten-5 alpha-ol (3), 3-phenyl-2-cholesten-5 alpha-ol (4), and 3 alpha H-2'-oxofuro-[2,3]cholestan-5 alpha-ol (5) were prepared in order to test a new tandem beta-fragmentation-cycloperoxyiodination reaction. The alkoxy radicals generated by irradiation of these alcohols with visible light in the presence of (diacetoxyiodo)benzene, I-2, and molecular oxygen undergo a beta-fragmentation reaction with subsequent peroxidation of the C-radical formed. This peroxy radical is added to conveniently positioned double bonds to give 10-membered cyclic ketones possessing a 1,2-dioxolane group.