17α-Hexanoyloxy-16-methylen-19-nor-progesteron | 21842-88-6

• 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: 17α-Hexanoyloxy-16-methylen-19-nor-progesteron
• 英文别名: [(8R,9S,10R,13S,14S,17R)-17-acetyl-13-methyl-16-methylidene-3-oxo-2,6,7,8,9,10,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl] hexanoate
• CAS: 21842-88-6
• 化学式: C₂₇H₃₈O₄
• 分子量: 426.596
• InChiKey: NAYYDGDMCVRDSY-WOSSHHRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  醋酸烯诺孕酮 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 17α-Hexanoyloxy-16-methylen-19-nor-progesteron
  参考文献：
  名称：

  Synthesewege zum 17α‐Hydroxy‐16‐methylen‐19‐nor‐progesteron und seinen Derivaten

  摘要：

  AbstractVerschiedene Synthesewege zum 17α‐Hydroxy‐16‐methylen‐19‐nor‐progesteron (4a) und seinen Derivaten werden beschrieben. Die C‐19‐Funktionalisierung wird in jedem Falle über eine Barton‐Reaktion durchgeführt. Zum Teil bisher nicht beschriebene Nebenprodukte dieser Reaktion und der Folgereaktionen werden isoliert und aufgeklärt. Sie gestatten einen genaueren Einblick in die Reaktionsabläufe.

  DOI：

  10.1002/cber.19691020231

文献信息

• Synthesis and progestational activity of 16-methylene-17α-hydroxy-19-norpregn-4-ene-3,20-dione and its derivatives
  作者：Fang Li、Narender Kumar、Yun-Yen Tsong、Carl Monder、C.Wayne Bardin

  DOI：10.1016/s0039-128x(97)00005-6

  日期：1997.5

  16-Methylnee-17 alpha-hydroxy-19-norpregn-4-ene-3,20-dione 1 and its 17 alpha-acylated derivatives were synthesized. The length of the 17 alpha-side-chain ranges from C-2-C-6. As anticipated, compound 1 did not show any progestational activity or receptor binding activity; whereas, the acylated compounds, especially the butyrate, showed remarkable ability to bind to progesterone receptors. These compounds also showed progestational activity in an in vitro T47D cell culture assay in which progestins increase alkaline phosphatase activity and in an in vivo ovulation inhibition assay. All of the compounds synthesized were without estrogenic activities. The results showed that acylation of 16-methylene-17 alpha-hydroxy-19-norprogesterone can increase progestational activity. The progestational activities of these compounds varied with the 17 alpha-side chain. (C) 1997 by Elsevier Science Inc.