16α-prop-2'-enylpregnen-4-en-3,20-dione | 196086-09-6

• 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-prop-2'-enylpregnen-4-en-3,20-dione
• 英文别名: 16α-prop-2'-enylprogesterone；(8S,9S,10R,13S,14S,16R,17S)-17-acetyl-10,13-dimethyl-16-prop-2-enyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 196086-09-6
• 化学式: C₂₄H₃₄O₂
• 分子量: 354.533
• InChiKey: HMGUIPQZMUKSBU-VAVNUEAYSA-N

物化性质

• 沸点：
  476.3±45.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  16α-prop-2'-enylpregnen-4-en-3,20-dione 在 AD-mix-β 、 水 作用下， 以 叔丁醇 为溶剂， 以65%的产率得到16α-prop-2',3'-diol-1'-ylpregn-4-en-3,20-dione
  参考文献：
  名称：

  Synthesis of potential pregnenolone and progesterone spin probes for biomembranes and immunoassays

  摘要：

  The synthesis and characterization of four new steroidal spin labels, viz., 3'-[[(pregn-5-en-3 beta-ol-20S-yl)methyl]oate]- 2',2',5',5'-tetramethylpyrrolidine-1'-oxyl,3'-[[(pregn-4-en-3- one-20S-yl)methyl]oate]-2',2',5'.5'-tetra methyl pyrrolidine-1'-oxyl, 3 "[(3 beta-acetoxypregn-5-en-20-one-16 alpha-yl)prop-2'xi-ol-3'xi-oate]-2 ",2 ",5 ",5 "-tetramethyl pyrrolidine-1 "-oxyl and 3 "-[(pregn-5-en-3,20-dione-16 alpha-yl)prop-2'xi-ol-3'xi-oate]-2',2',5',5'-tetramethylpyrrolidine-1'-oxyl has been described which involves functionalization of the parent hormone at C-20 and C-16. The key step to all the products was the condensation of 3-carboxyproxyl with the derivatized synthons. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01187-9
• 作为产物：
  描述：

  16-脱氢孕烯醇酮乙酸酯 在 氢氧化钾 、 四氯化钛 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 16α-prop-2'-enylpregnen-4-en-3,20-dione
  参考文献：
  名称：

  Synthesis of potential pregnenolone and progesterone spin probes for biomembranes and immunoassays

  摘要：

  The synthesis and characterization of four new steroidal spin labels, viz., 3'-[[(pregn-5-en-3 beta-ol-20S-yl)methyl]oate]- 2',2',5',5'-tetramethylpyrrolidine-1'-oxyl,3'-[[(pregn-4-en-3- one-20S-yl)methyl]oate]-2',2',5'.5'-tetra methyl pyrrolidine-1'-oxyl, 3 "[(3 beta-acetoxypregn-5-en-20-one-16 alpha-yl)prop-2'xi-ol-3'xi-oate]-2 ",2 ",5 ",5 "-tetramethyl pyrrolidine-1 "-oxyl and 3 "-[(pregn-5-en-3,20-dione-16 alpha-yl)prop-2'xi-ol-3'xi-oate]-2',2',5',5'-tetramethylpyrrolidine-1'-oxyl has been described which involves functionalization of the parent hormone at C-20 and C-16. The key step to all the products was the condensation of 3-carboxyproxyl with the derivatized synthons. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01187-9

文献信息

• Oxidation of Steroidal 5-En-3β-ol with Pyridinium Chlorochromate: Isolation of Key Intermediate, Steroidal 6β-Hydroxy-4-en-3-one
  作者：S. S. Korde、R. A. Udasi、G. K. Trivedi

  DOI：10.1080/00397919708005643

  日期：1997.10

  The PCC oxidation of 5-en-3 beta-ol steroids proceeds to 4-en-3,6-dione through the intermediate 5-en-3-one. The isolation of another key intermediate, steroidal 6 beta-hydroxy-4-en-3-one guides an understanding of the mechanism involved.