16α,17α-epoxy-17β-ethynylandrosta-4-en-3-one | 127799-30-8

• 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: 16α,17α-epoxy-17β-ethynylandrosta-4-en-3-one
• 英文别名: 16α,17α-epoxy-17β-ethynylandrost-4-en-3-one；16α,17α-Epoxypregn-4-en-3-one-20-yne；(1R,2S,4R,6S,7S,10S,11R)-6-ethynyl-7,11-dimethyl-5-oxapentacyclo[8.8.0.02,7.04,6.011,16]octadec-15-en-14-one
• CAS: 127799-30-8
• 化学式: C₂₁H₂₆O₂
• 分子量: 310.436
• InChiKey: UOWHCOUHKMSBCE-SRWWVFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  29.6
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  16α,17α-epoxy-17β-ethynylandrosta-4-en-3-one 在 吡啶 作用下， 生成 16α-acetoxy-17α-methoxypregn-4-en-3-on-20-yne
  参考文献：
  名称：

  Transformed steroids. 185. Use of the Nicholas reaction for regio- and stereo-selective transformation of 16?,17a-epoxy-17?-ethynyl-androstanes into 16?,17?-cis-disubstituted steroids

  摘要：

  The HBF4.Et2O-catalyzed methanolysis reactions of the 16-alpha,17-alpha-oxides of 17-beta-ethynylandrost-4-en-3-one and its dicobalt hexacarbonyl complex were studied. It was shown that these reactions proceed with the same regiodirectivity of the oxide ring opening at the tertiary center but with a different mode of stabilization of the intermediates formed. The reaction of the free oxide proceeds without the inclusion of the external nucleophile and is concluded by the Wagner-Meerwein rearrangement; the C-17-carbocation formed in the Co-coordinated oxide is stabilized by the addition of the methoxide ion and the elimination of a proton or of water. The opening of the oxide ring of dicobalt tetracarbonyl 16-alpha, 17-alpha-epoxy-17-beta-ethynylandrost-4-en-3-one can be realized with decomplexation accompanied by carbonylation and heterocyclization.

  DOI：

  10.1007/bf00961374
• 作为产物：
  描述：

  炔孕酮 在 2,4-二甲基吡啶 、 间氯过氧苯甲酸 、 三氯氧磷 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 7.0h， 生成 16α,17α-epoxy-17β-ethynylandrosta-4-en-3-one
  参考文献：
  名称：

  Transformed steroids. 176. Paths of transformation of 17a-ethynyl-17?-hydroxyandrostenes into ?16-21-hydroxy-20-ketopregnenes

  摘要：

  DOI：

  10.1007/bf00962448

文献信息

• Transformed steroids. 190. Influence of Co-complexation on the epoxide ring opening of 17?-ethynyl-16?,17?-epoxyandrost-4-en-3-one on reacting with pyridine hydrofluoride, pyridine hydrochloride, and pyridine thiocyanate
  作者：A. M. Turuta、A. V. Kamernitskii、Luu Dik Hi、V. S. Bogdanov

  DOI：10.1007/bf00863381

  日期：1992.11

  The epoxide ring opening of 16alpha, 17alpha-epoxy-17beta-ethynylandrost-4-en-3-one and its dicobalt hexacarbonyl complex on reacting with Py . HF, Py . HCl, and Py . HSCN was studied. The results of these reactions and the structure of the end products depend wt only on the complexation of the acetylene bond, but also on the nucleophilic reagent used. On the basis of the reaction of a Co-coordinated 16alpha, 17alpha-epoxy-17beta-ethynylandrost-4-en-3-one there has been developed a preparative method for the synthesis of pregn-4-ene-3,20-dione-[17alpha, 16alpha-d]-1',3'-oxazolidin-2'-one.
• TURUTA, A. M.;FADEEVA, T. M.;KAMERNITSKIJ, A. V.;XI, LYU DYK, IZV. AN CCCP. CEP. XIM.,(1989) N2, S. 2810-2815
  作者：TURUTA, A. M.、FADEEVA, T. M.、KAMERNITSKIJ, A. V.、XI, LYU DYK

  DOI：——

  日期：——
• TURUTA, A. M.;KAMERNITSKIJ, A. V.;LYU, DYK XI;FADEEVA, T. M., IZV. AN CCCP. CEP. XIM.,(1991) N, S. 1180-1184
  作者：TURUTA, A. M.、KAMERNITSKIJ, A. V.、LYU, DYK XI、FADEEVA, T. M.

  DOI：——

  日期：——