3β-chloro-5,7α-dibromo-5α-cholestan-6-one | 501115-50-0

• 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: 3β-chloro-5,7α-dibromo-5α-cholestan-6-one
• 英文别名: 3b-Chloro-5,7a-dibromo-5a-cholestan-6-one；(3S,5R,7S,8S,9S,10R,13R,14S,17R)-5,7-dibromo-3-chloro-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-one
• CAS: 501115-50-0
• 化学式: C₂₇H₄₃Br₂ClO
• 分子量: 578.899
• InChiKey: KHJWFPKSBDORBG-DEXMOYKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3β-chloro-5,7α-dibromo-5α-cholestan-6-one 在 lithium carbonate 、 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以36%的产率得到7α-bromo-cholesta-2,4-dien-6-one
  参考文献：
  名称：

  摘要：

  3beta-Chloro-5alpha, 7alpha-dibromo-6-ketosteroids 5a and 5b are synthesized from beta-sitosterol (1a) and cholesterol (1b). Dehydrohalogenation of these forms 7alpha-bromo-2,4-dien-6-ones (6a-b), 2,4-dien-6-ones (7a-b), and 14alpha-hydroperoxy-2,4,7-trien-6-ones (8a-b). Woodward hydroxylation of dienone 6a produces 2beta-iodo-7alpha-bromo-3alpha-acetoxy-Delta(4)-6-ketone 9 and 7alpha-bromo-2alpha,3alpha-diacetoxy-Delta(4)-6-ketone 10. 2beta-Iodo-3alpha-acetoxy-Delta(4,7,14)-trien-6-one 11 is Prepared analogouslyfrom trienone 8a.

  DOI：

  10.1023/a:1020432027888
• 作为产物：
  描述：

  3β-chloro-5-bromo-5α-cholestan-6-one 在 氢溴酸 、 溴 作用下， 以 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 反应 7.0h， 以79%的产率得到3β-chloro-5,7α-dibromo-5α-cholestan-6-one
  参考文献：
  名称：

  摘要：

  3beta-Chloro-5alpha, 7alpha-dibromo-6-ketosteroids 5a and 5b are synthesized from beta-sitosterol (1a) and cholesterol (1b). Dehydrohalogenation of these forms 7alpha-bromo-2,4-dien-6-ones (6a-b), 2,4-dien-6-ones (7a-b), and 14alpha-hydroperoxy-2,4,7-trien-6-ones (8a-b). Woodward hydroxylation of dienone 6a produces 2beta-iodo-7alpha-bromo-3alpha-acetoxy-Delta(4)-6-ketone 9 and 7alpha-bromo-2alpha,3alpha-diacetoxy-Delta(4)-6-ketone 10. 2beta-Iodo-3alpha-acetoxy-Delta(4,7,14)-trien-6-one 11 is Prepared analogouslyfrom trienone 8a.

  DOI：

  10.1023/a:1020432027888

文献信息

• ——
  作者：N. V. Kovganko、V. L. Survilo

  DOI：10.1023/a:1020432027888

  日期：——

  3beta-Chloro-5alpha, 7alpha-dibromo-6-ketosteroids 5a and 5b are synthesized from beta-sitosterol (1a) and cholesterol (1b). Dehydrohalogenation of these forms 7alpha-bromo-2,4-dien-6-ones (6a-b), 2,4-dien-6-ones (7a-b), and 14alpha-hydroperoxy-2,4,7-trien-6-ones (8a-b). Woodward hydroxylation of dienone 6a produces 2beta-iodo-7alpha-bromo-3alpha-acetoxy-Delta(4)-6-ketone 9 and 7alpha-bromo-2alpha,3alpha-diacetoxy-Delta(4)-6-ketone 10. 2beta-Iodo-3alpha-acetoxy-Delta(4,7,14)-trien-6-one 11 is Prepared analogouslyfrom trienone 8a.