des-A-17β-t-butoxy-9-estren-5-one | 38255-63-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: des-A-17β-t-butoxy-9-estren-5-one
• 英文别名: <3S-(3α,3aα,9aα,9bβ)>-3-(1,1-Dimethylethoxy)-1,2,3,3a,4,5,8,9a,9b-decahydro-3a-methyl-7H-benzinden-7-one；<3S-(3α,3aα,9aα,9bβ)>-3-(1,1-dimethylethoxy)-1,2,3,3a,4,5,8,9,9a,9b-decahydro-3a-methyl-7H-benzinden-7-one；[3S-(3α,3aα,9aα,9bβ)]-3-(1,1-Dimethylethoxy)-1,2,3,3a,4,5,8,9,9a,9b-decahydro-3a-methyl-7H-benz[e]inden-7-one；(3S,3aS,9aS,9bS)-3a-methyl-3-[(2-methylpropan-2-yl)oxy]-2,3,4,5,8,9,9a,9b-octahydro-1H-cyclopenta[a]naphthalen-7-one
• CAS: 38255-63-9
• 化学式: C₁₈H₂₈O₂
• 分子量: 276.419
• InChiKey: RYXQQNUSOVMLNL-CVYDXHPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  des-A-17β-t-butoxy-9-estren-5-one 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以90%的产率得到<3S-(3α,3aα,9aα,9bβ)>-1,2,3,3a,4,5,8,9,9a,9b-Decahydro-3-hydroxy-3a-methyl-7H-benzinden-7-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：

  (1S,7aS)-1-tert-butoxy-7a-methyl-1,2,3,6,7,7a-hexahydro-5H-inden-5-one 在 palladium on activated charcoal 盐酸 、 丙二酸 、 氢气 、 sodium methylate 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 乙酸乙酯 、 丙酮 、 苯 为溶剂， 反应 38.5h， 生成 des-A-17β-t-butoxy-9-estren-5-one
  参考文献：
  名称：

  [1,2,3,4-13C]睾丸激素和[1,2,3,4-13C]雌二醇。

  摘要：

  描述了通过全合成制备[1,2,3,4-13C]睾丸激素和[1,2,3,4-13C]雌二醇。通过用[1,2,3,4-13C] 1-碘-3,3-亚乙基二氧丁烷（2）烷基化中间体1来引入13C标记，以获得中间体10。缩酮功能的水解，环化，芳构化和去除保护基产生[1,2,3,4-13C]雌二醇。通过使中间体10甲基化并随后用酸处理来制备标记的睾丸激素。标记的类固醇可以用作体内代谢研究的示踪剂，也可以用作确定性gc-ms定量方法开发的内部标准。

  DOI：

  10.1016/s0039-128x(84)80021-5

文献信息

• Neurosteroid Analogs. 3. The Synthesis and Electrophysiological Evaluation of Benz[e]indene Congeners of Neuroactive Steroids Having the 5.beta.-Configuration
  作者：Mingcheng Han、Yuefei Hu、Charles F. Zorumski、Douglas F. Covey

  DOI：10.1021/jm00022a021

  日期：1995.10

  series of 7-(2-hydroxyethyl)benz[e]indene analogues of 3 alpha-hydroxy-5 beta-pregnan-20-one (7), a neuroactive steroid known to be a positive allosteric modulator of GABAA receptor function, was prepared. Electrophysiological measurements carried out on cultured rat hippocampal neurons were used to evaluate the modulatory effects of the analogues on GABAA receptor function. Analogues were tested for

  3α-羟基-5β-pregnan-20-one（7）的一系列7-（2-羟乙基）苯并[e]茚类似物是一种神经活性类固醇，已知是GABAA受体功能的正变构调节剂。准备好了。在培养的大鼠海马神经元上进行的电生理测量用于评估类似物对GABAA受体功能的调节作用。测试了类似物增强1 microM GABA介导的氯离子电流的能力，以及在该配体门控离子通道上直接控制氯离子电流的能力。活性类似物通常以低于直接控制氯离子电流所需浓度的浓度增强GABA介导的电流。研究了[3S-（3 alpha，3a alpha，5a beta，7 beta，9a alpha，9b beta）]-1- [十二烷基-7-（2-羟乙基）-3a-甲基-1H-苯并[e]茚满-3-基]乙酮（3），甾族化合物7，3α-羟基-5α- pregnan-20-one（5）和类固醇5的7α-（2-羟乙基）苯并[e]茚烯类似物（化合物1）。化合物3
• Benz(epsilon)indene compounds
  申请人：Washington University

  公开号：US05434274A1

  公开（公告）日：1995-07-18

  Neuroactive benz[e]indene compounds ##STR1## are prepared by a total synthesis from the following three starting materials ##STR2##

  神经活性苯并[e]茚化合物##STR1##是通过从以下三种起始物质进行总合成而制备的##STR2##
• US5434274A
  申请人：——

  公开号：US5434274A

  公开（公告）日：1995-07-18
• [1,2,3,4-13C] Testosterone and [1,2,3,4-13C] estradiol
  作者：Gijsbert Zomer、Hans Wynberg、Nick M. Drayer

  DOI：10.1016/s0039-128x(84)80021-5

  日期：1984.10

  preparation of [1,2,3,4-13C] testosterone and of [1,2,3,4-13C] estradiol by total synthesis is described. The 13C labels are introduced by alkylating intermediate 1 with [1,2,3,4-13C]l-iodo-3,3-ethylenedioxybutane (2) to obtain intermediate 10. Hydrolysis of the ketal function, cyclization, aromatization and removal of protective groups gave [1,2,3,4-13C] estradiol. Labeled testosterone was prepared by methylating

  描述了通过全合成制备[1,2,3,4-13C]睾丸激素和[1,2,3,4-13C]雌二醇。通过用[1,2,3,4-13C] 1-碘-3,3-亚乙基二氧丁烷（2）烷基化中间体1来引入13C标记，以获得中间体10。缩酮功能的水解，环化，芳构化和去除保护基产生[1,2,3,4-13C]雌二醇。通过使中间体10甲基化并随后用酸处理来制备标记的睾丸激素。标记的类固醇可以用作体内代谢研究的示踪剂，也可以用作确定性gc-ms定量方法开发的内部标准。
• Neurosteroid Analogs. 2. Total Synthesis and Electrophysiological Evaluation of Benz[e]indene Analogs of the Anesthetic Steroid Alphaxalone
  作者：Yuefei Hu、Charles F. Zorumski、Douglas F. Covey

  DOI：10.1021/jo00117a010

  日期：1995.6

  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.