6α-chlorocholest-4-en-3-one | 3729-76-8

• 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: 6α-chlorocholest-4-en-3-one
• 英文别名: 6α-chloro-cholest-4-en-3-one；6α-Chlor-cholest-4-en-3-on；(6S,8S,9S,10R,13R,14S,17R)-6-chloro-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 3729-76-8
• 化学式: C₂₇H₄₃ClO
• 分子量: 419.091
• InChiKey: DRXUABCBPYUCJB-FQIKLQBFSA-N

物化性质

• 熔点：
  125-126 °C
• 沸点：
  509.6±19.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  6α-chlorocholest-4-en-3-one 在 lithium tri-t-butoxyaluminum hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 6α-chloro-4β,5-epoxy-5β-cholestan-3β-ol
  参考文献：
  名称：

  Synthesis of some analogues of blattellastanoside A, the steroidal aggregation pheromone of the German cockroach

  摘要：

  Blattellastanoside A, the aggregation pheromone of the German cockroach, is a chlorinated steroid glucoside with the 5 beta-stigmastane skeleton. Its analogues were synthesized in order to clarify the structure-activity relationship. They are 1a with the 5 beta-cholestane skeleton, 1b with the 5 beta-androstane skeleton, Ic with a fluorine substituent instead of the chlorine and Id with a beta-D-galactopyranose instead of the beta-D-glucopyranose of the original pheromone. Their bioassay shows that la and Ic are active, while Ib and Id are totally devoid of pheromone activity. The aglycone of blattellastanosides A and B were active. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00018-1
• 作为产物：
  描述：

  5,6-epoxycholesterol 在 chromium(VI) oxide 、 盐酸 、 magnesium sulfate 作用下， 以 二氯甲烷 、 氯仿 、 丙酮 为溶剂， 反应 3.5h， 生成 6α-chlorocholest-4-en-3-one
  参考文献：
  名称：

  Synthesis of some analogues of blattellastanoside A, the steroidal aggregation pheromone of the German cockroach

  摘要：

  Blattellastanoside A, the aggregation pheromone of the German cockroach, is a chlorinated steroid glucoside with the 5 beta-stigmastane skeleton. Its analogues were synthesized in order to clarify the structure-activity relationship. They are 1a with the 5 beta-cholestane skeleton, 1b with the 5 beta-androstane skeleton, Ic with a fluorine substituent instead of the chlorine and Id with a beta-D-galactopyranose instead of the beta-D-glucopyranose of the original pheromone. Their bioassay shows that la and Ic are active, while Ib and Id are totally devoid of pheromone activity. The aglycone of blattellastanosides A and B were active. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00018-1

文献信息

• Wicha,J.; Zarecki,A., Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1976, vol. 24, p. 357 - 362
  作者：Wicha,J.、Zarecki,A.

  DOI：——

  日期：——
• Stereochemistry of the Cholesterol Dichlorides¹
  作者：D. H. R. Barton、E. Miller

  DOI：10.1021/ja01157a100

  日期：1950.1