(22E)-3,3-difluoro-5α-stigmast-22-en-6-one | 1322075-43-3

• 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: (22E)-3,3-difluoro-5α-stigmast-22-en-6-one
• CAS: 1322075-43-3
• 化学式: C₂₉H₄₆F₂O
• 分子量: 448.68
• InChiKey: IRVHAWQEKIIHQV-CYGCVKBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.33
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (22E)-3,3-difluoro-5α-stigmast-22-en-6-one 在 potassium osmate(VI) dihydrate 、 甲基磺酰胺 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 168.0h， 以68%的产率得到(22R,23R)-3,3-difluoro-22,23-dihydroxy-5α-stigmastan-6-one
  参考文献：
  名称：

  Synthesis and biological activity of ring-A difluorinated brassinosteroids

  摘要：

  In this paper we report the synthesis of four ring-A difluorinated analogs of brassinosteroids. The bioactivity of these new compounds was evaluated using the rice lamina inclination test. The results show that one of these analogs elicits a bioactivity comparable to that of 28-homocastasterone, a highly active natural brassinosteroid. This finding suggests that both hydroxyls at C-2 and C-3 in active brassinosteroids are involved as hydrogen bond acceptors in their interactions with the cellular receptor. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.04.004
• 作为产物：
  描述：

  22E,24R-stigmast-22-ene-3,6-dione 在 二乙胺基三氟化硫 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以59%的产率得到(22E)-3,3-difluoro-5α-stigmast-22-en-6-one
  参考文献：
  名称：

  Synthesis and biological activity of ring-A difluorinated brassinosteroids

  摘要：

  In this paper we report the synthesis of four ring-A difluorinated analogs of brassinosteroids. The bioactivity of these new compounds was evaluated using the rice lamina inclination test. The results show that one of these analogs elicits a bioactivity comparable to that of 28-homocastasterone, a highly active natural brassinosteroid. This finding suggests that both hydroxyls at C-2 and C-3 in active brassinosteroids are involved as hydrogen bond acceptors in their interactions with the cellular receptor. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.04.004