1α,11α-epoxy-5β-pregnane-3,20-dione | 854988-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1α,11α-epoxy-5β-pregnane-3,20-dione
• 英文别名: (1R,3S,4S,7S,8S,11R,15S,16S,17S)-4-acetyl-3,16-dimethyl-18-oxapentacyclo[13.2.1.03,7.08,17.011,16]octadecan-13-one
• CAS: 854988-19-5
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: FMLDUHIBQBNODC-ZXAJKFLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1α,11α-epoxy-5β-pregnane-3,20-dione 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (5R,8S,9S,10R,11R,13S,14S,17S)-17-Acetyl-11-hydroxy-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
  参考文献：
  名称：

  Synthesis of C(1)–C(11) oxygen-bridged pregnanes

  摘要：

  A general procedure for the synthesis of 1 alpha,11 alpha- and 1 beta,11 alpha-epoxysteroids is described, using an intramolecular remote functionalization reaction involving the photolysis of 11 alpha-hydroxysteroids in the presence of diacetoxyiodobenzene and iodine. Three 1,11-epoxypregnanes were prepared, two of them (compounds 10 and 14) are conformationally constrained analogues of steroidal hormones, compound 13 is a synthetic precursor of neurosteroids. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.052
• 作为产物：
  描述：

  Acetic acid (3R,5R,8S,9S,10S,11R,13S,14S,17S)-17-((R)-1-acetoxy-ethyl)-11-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 在 lithium aluminium tetrahydride 、 碘苯二乙酸 、 4 A molecular sieve 、 碘 、 barium carbonate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 1α,11α-epoxy-5β-pregnane-3,20-dione
  参考文献：
  名称：

  Synthesis of C(1)–C(11) oxygen-bridged pregnanes

  摘要：

  A general procedure for the synthesis of 1 alpha,11 alpha- and 1 beta,11 alpha-epoxysteroids is described, using an intramolecular remote functionalization reaction involving the photolysis of 11 alpha-hydroxysteroids in the presence of diacetoxyiodobenzene and iodine. Three 1,11-epoxypregnanes were prepared, two of them (compounds 10 and 14) are conformationally constrained analogues of steroidal hormones, compound 13 is a synthetic precursor of neurosteroids. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.052