(22E)-6α-fluorostigmasta-2,22-diene | 850407-39-5

• 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)-6α-fluorostigmasta-2,22-diene
• 英文别名: (5S,6S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-6-fluoro-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene
• CAS: 850407-39-5
• 化学式: C₂₉H₄₇F
• 分子量: 414.691
• InChiKey: BPYQHNUJILABEC-GQVSAKLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (22E)-6α-fluorostigmasta-2,22-diene 在 甲基磺酰胺 、 potassium carbonate potassium osmate(VI) 、 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 216.0h， 以35%的产率得到(22R,23R)-6α-fluorostigmasta-2α,3α,22,23-tetraol
  参考文献：
  名称：

  Synthesis and bioactivity of C-29 brassinosteroid analogues with different functional groups at C-6

  摘要：

  In this paper, we report the synthesis and bioactivity of four synthetic analogues of 28-homobrassinosteroids, in order to evaluate the influence in bioactivity when the C-6 keto group is replaced by different functional groups. The synthetic analogues are 6-deoxo-28-homocastasterone [(22R,23R)-stigmasta-2 alpha,3 alpha,22,23-tetraol], 6 alpha-hydroxy-28-homocastasterone [(22R,23R)-stigmasta-2 alpha,3ot,6 alpha, 22,23-pentaol], 6 beta-hydroxy-28-homocastasterone [(22R,23R)-stigmasta-2 alpha,3 alpha,6 beta,22,23-pentaol], and [(22R,23R)-6 alpha-fluorostigmasta-2 alpha,3 alpha,22,23-tetraol].Results indicate that replacement of the 6-keto moiety by an beta or alpha hydroxyl group led to a decrease in activity, whereas the 6deoxo analogue showed a very low activity, confirming the importance of an electronegative moiety at C-6 to observe hormonal potency. The 6 alpha-fluorinated analogue elicited a low activity, similar to that of the 6-deoxo analogue. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2004.12.029
• 作为产物：
  描述：

  (22E)-stigmasta-2,22-dien-6-one 在 乙醇 、 二乙胺基三氟化硫 、 sodium 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (22E)-6α-fluorostigmasta-2,22-diene
  参考文献：
  名称：

  Synthesis and bioactivity of C-29 brassinosteroid analogues with different functional groups at C-6

  摘要：

  In this paper, we report the synthesis and bioactivity of four synthetic analogues of 28-homobrassinosteroids, in order to evaluate the influence in bioactivity when the C-6 keto group is replaced by different functional groups. The synthetic analogues are 6-deoxo-28-homocastasterone [(22R,23R)-stigmasta-2 alpha,3 alpha,22,23-tetraol], 6 alpha-hydroxy-28-homocastasterone [(22R,23R)-stigmasta-2 alpha,3ot,6 alpha, 22,23-pentaol], 6 beta-hydroxy-28-homocastasterone [(22R,23R)-stigmasta-2 alpha,3 alpha,6 beta,22,23-pentaol], and [(22R,23R)-6 alpha-fluorostigmasta-2 alpha,3 alpha,22,23-tetraol].Results indicate that replacement of the 6-keto moiety by an beta or alpha hydroxyl group led to a decrease in activity, whereas the 6deoxo analogue showed a very low activity, confirming the importance of an electronegative moiety at C-6 to observe hormonal potency. The 6 alpha-fluorinated analogue elicited a low activity, similar to that of the 6-deoxo analogue. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2004.12.029