<3S-(3α,3aα,5aβ,7α,9aα,9bβ)>-3-Acetyl-7-<2-(trimethylacetyloxy)ethyl>dodecahydro-3a-methyl-5H-benzinden-5-one | 165753-77-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <3S-(3α,3aα,5aβ,7α,9aα,9bβ)>-3-Acetyl-7-<2-(trimethylacetyloxy)ethyl>dodecahydro-3a-methyl-5H-benzinden-5-one
• 英文别名: [3S-(3α,3aα,5aβ,7α,9aα,9bβ)]-3-Acetyl-7-[2-(trimethylacetyloxy)ethyl]dodecahydro-3a-methyl-5H-benz[e]inden-5-one；2-[(3S,3aS,5aR,7R,9aS,9bS)-3-acetyl-3a-methyl-5-oxo-2,3,4,5a,6,7,8,9,9a,9b-decahydro-1H-cyclopenta[a]naphthalen-7-yl]ethyl 2,2-dimethylpropanoate
• CAS: 165753-77-5
• 化学式: C₂₃H₃₆O₄
• 分子量: 376.536
• InChiKey: BUMWWLXTUXVYQX-KPEOFTLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  <3S-(3α,3aα,5aβ,7α,9aα,9bβ)>-3-Acetyl-7-<2-(trimethylacetyloxy)ethyl>dodecahydro-3a-methyl-5H-benzinden-5-one 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 60.0h， 以21%的产率得到<3R-(3α,3aβ,5aα,7β,9aβ,9bα)>-3-Acetyldodecahydro-7-(2-hydroxyethyl)-3a-methyl-5H-benzinden-5-one
  参考文献：
  名称：

  Neurosteroid Analogs. 2. Total Synthesis and Electrophysiological Evaluation of Benz[e]indene Analogs of the Anesthetic Steroid Alphaxalone

  摘要：

  Anesthetic steroid Pa and benz[e]indene 2 are known to have potent pharmacological actions at GABA(A) receptors. Anesthetic Il-ketosteroids such as alfaxalone (Ph) are also known to have this activity. Evaluation of corresponding 5H-benz[e]inden-5-one analogs of Il-ketosteroids necessitated the development of an efficient route to these compounds. Accordingly, total synthesis of the 5H-benz[e]inden-5-ones 3 and 4 from the known 5H-inden-5-one precursor 5 is described. The structure of compound 3 has been verified by X-ray diffraction analysis. Electrophysiological evaluations of compounds 3 and 4 indicate that, unlike benz[e]indene 2, these compounds have weak pharmacological actions at GABA(A) receptors.

  DOI：

  10.1021/jo00117a010
• 作为产物：
  描述：

  <3S-<3α(S*),3aα,5β,5aβ,7α,9aα,9bβ>>-Dodecahydro-5-hydroxy-3-(1-hydroxyethyl)-3a-methyl-1H-benzindene-7-ethanol trimethylacetate 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.08h， 以92%的产率得到<3S-(3α,3aα,5aβ,7α,9aα,9bβ)>-3-Acetyl-7-<2-(trimethylacetyloxy)ethyl>dodecahydro-3a-methyl-5H-benzinden-5-one
  参考文献：
  名称：

  Neurosteroid Analogs. 2. Total Synthesis and Electrophysiological Evaluation of Benz[e]indene Analogs of the Anesthetic Steroid Alphaxalone

  摘要：

  Anesthetic steroid Pa and benz[e]indene 2 are known to have potent pharmacological actions at GABA(A) receptors. Anesthetic Il-ketosteroids such as alfaxalone (Ph) are also known to have this activity. Evaluation of corresponding 5H-benz[e]inden-5-one analogs of Il-ketosteroids necessitated the development of an efficient route to these compounds. Accordingly, total synthesis of the 5H-benz[e]inden-5-ones 3 and 4 from the known 5H-inden-5-one precursor 5 is described. The structure of compound 3 has been verified by X-ray diffraction analysis. Electrophysiological evaluations of compounds 3 and 4 indicate that, unlike benz[e]indene 2, these compounds have weak pharmacological actions at GABA(A) receptors.

  DOI：

  10.1021/jo00117a010

文献信息

• US5434274A
  申请人：——

  公开号：US5434274A

  公开（公告）日：1995-07-18