17-acetoxy-2α,3α-isopropylidendioxy-6,6-ethylenedioxy-5α-androsta-14,16-diene | 1346236-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 17-acetoxy-2α,3α-isopropylidendioxy-6,6-ethylenedioxy-5α-androsta-14,16-diene
• CAS: 1346236-22-3
• 化学式: C₂₆H₃₆O₆
• 分子量: 444.568
• InChiKey: DVJLMPDFRTZCQJ-QKLQQXTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  32.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  17-acetoxy-2α,3α-isopropylidendioxy-6,6-ethylenedioxy-5α-androsta-14,16-diene 在 碳酸氢钠 、 三苯基膦 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 20.0h， 生成 14β-cyanomethyl-6,6-ethylenedioxy-2α,3α-isopropylidendioxy-5α-androst-15-en-17-one
  参考文献：
  名称：

  Diels–Alder reaction of androsta-14,16-dien-17-yl acetates with nitroethylene: Product distribution and selected adduct transformations

  摘要：

  The Diels-Alder cycloaddition of nitroethylene to some androsta-14,16-dien-17-yl acetates has been studied. The addition occurs stereoselectively, giving predominantly head-to-head-adduct. 14 beta-Cyanomethyl steroids were obtained via the reductive cleavage reaction of bridged nitro compounds. The structures of the new compounds have been fully characterized by 2D NMR and tandem mass-spectrometry methods. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.11.015
• 作为产物：
  描述：

  2α,3α-isopropylidenedioxy-6,6-ethylenedioxy-5α-androst-15-en-17-one 在 1,10-菲罗啉 、 silica gel 、 二异丙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 、 苯 为溶剂， 反应 12.53h， 生成 17-acetoxy-2α,3α-isopropylidendioxy-6,6-ethylenedioxy-5α-androsta-14,16-diene
  参考文献：
  名称：

  Synthesis of 14,16-dien-17-yl acetates of androstane series. NMR and mass spectrometry data

  摘要：

  On the basis of dehydroepiandrosterone through the Delta(14)- and Delta(15)-androst-17-ones a series of androsta-14,16-dienyl acetates was obtained, the key compounds in the synthesis of 14-substituted steroids. By the methods of two-dimensional NMR spectroscopy the structure of compounds was proved and a full assignment of signals in the H-1 and C-13 NMR spectra was performed. With the use of tandem mass spectrometry the main directions of fragmentation of protonated molecules of the synthesized ketones and dienyl acetates were studied. DOI: 10.1134/S1070363211090234

  DOI：

  10.1134/s1070363211090234

文献信息

• Synthesis of 14α-substituted androstanes—Key compounds in the synthesis of 14-substituted brassinosteroids
  作者：A. V. Baranovskii、D. A. Bolibrukh、B. Schneider

  DOI：10.1134/s1070428015010133

  日期：2015.1

  Ethyl 3-(6,6-ethylenedioxy-2 alpha,3 alpha-isopropylidenedioxy-17-oxo-5 alpha-androstan-14 alpha-yl)propanoate, the key intermediate product in the synthesis of brassinosteroids modified in the D ring, was synthesized from 6,6-ethylenedioxy-2 alpha,3 alpha-isopropylidenedioxy-5 alpha-androsta-14,16-dien-17-yl acetate via reaction sequence including Diels-Alder cycloaddition with phenyl vinyl sulfone, dihydroxylation, Malaprade diol cleavage, and selective Horner-Wadsworth-Emmons olefination.