(E)-3β,17β-diacetoxy-5,10-secoandrost-1(10)-en-5-one | 51261-50-8

• 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: (E)-3β,17β-diacetoxy-5,10-secoandrost-1(10)-en-5-one
• 英文别名: [(1S,2E,5S,10R,11S,14S,15S)-5-acetyloxy-2,15-dimethyl-7-oxo-14-tricyclo[8.7.0.011,15]heptadec-2-enyl] acetate
• CAS: 51261-50-8
• 化学式: C₂₃H₃₄O₅
• 分子量: 390.52
• InChiKey: MOYXWDGKVIVTHT-GTFAIHKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3β,17β-diacetoxy-5,10-secoandrost-1(10)-en-5-one 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以68%的产率得到5-hydroxy-5-(10<*>1βH)abeo-α-androst-10(19)-ene-3β,17β-diyl-diacetate
  参考文献：
  名称：

  Lorenc, Ljubinka; Rajkovic, Milica; Milovanovic, Aleksandar, Journal of the Chemical Society. Perkin transactions I, 1988, p. 1495 - 1498

  摘要：

  DOI：
• 作为产物：
  描述：

  5-hydroxy-5α-androstane-3β,17β-diyl-3,17-diacetate 生成 (E)-3β,17β-diacetoxy-5,10-secoandrost-1(10)-en-5-one
  参考文献：
  名称：

  MIHAILOVIC, MIHAILO LJ.;LORENC, LJUBINKA;FORSEK, JOZE;PAVLOVIC, VLADIMIR;+, J. SERB. CHEM. SOC., 54,(1989) N2, C. 645-656

  摘要：

  DOI：

文献信息

• Synthesis of 5,10-seco analogs of testosterone
  作者：Vladimir A. Khripach、Vladimir N. Zhabinskii、Anna I. Kuchto、Yuliya Y. Zhiburtovich、Natalya B. Khripach、Alexander S. Lyakhov、Marinus B. Groen、Jaap van der Louw、Aede de Groot

  DOI：10.1016/j.steroids.2008.07.005

  日期：2008.12

  A number of 5,10-seco analogs of testosterone has been synthesized starting from products of the radical oxidation of 3 beta,17 beta-diacetoxy-5 alpha-androstan-5 alpha-ol. The obtained compounds possess a flexible 10-membered ring with substituents (=O, -OH) at C-3 and C-5. Similar derivatives with an (E)- and (Z)-Delta(1(10))-double bond have been prepared also. X-ray analysis and a combination of NMR experiments have been used for their structure elucidation and conformation analysis. (C) 2008 Published by Elsevier Inc.
• Tinant, B.; Declercq, J. P.; Meerssche, M. Van, Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 7, p. 485 - 492
  作者：Tinant, B.、Declercq, J. P.、Meerssche, M. Van、Mihailovic, M. Lj.、Lorenc, Lj.、et al.

  DOI：——

  日期：——
• Intramolecular cycloaddition/cycloreversion of (E)-3β,17β-diacetoxy-5,10-secoandrost-1(10)-en-5-one
  作者：Vladimir A. Khripach、Vladimir N. Zhabinskii、Anna I. Kuchto、Yuliya Y. Zhiburtovich、Vladimir V. Gromak、Marinus B. Groen、Jaap van der Louw、Aede de Groot

  DOI：10.1016/j.tetlet.2006.07.096

  日期：2006.9

  Treatment of 3 beta,17 beta-diacetoxy-5,10-secoandrost-1(10)-en-5-one with (BF3Et2O)-Et-. was shown to proceed with cleavage of the macrocycle and formation of a new compound containing a cyclopentenone ring. Based on DFT calculations, an intramolecular Lewis acid promoted [2+2]cycloaddition, followed by a cycloreversion of the intermediate oxetane, is proposed as a possible reaction mechanism. (c) 2006 Elsevier Ltd. All rights reserved.