(22E)-5-fluoro-5α-stigmasta-2,22-dien-6-one | 301699-56-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (22E)-5-fluoro-5α-stigmasta-2,22-dien-6-one
• 英文别名: (22E)-5α-fluorostigmasta-2,22-dien-6-one；(5R,8S,9S,10R,13R,14S,17R)-17-[(E,1R,4S)-4-ethyl-1,5-dimethyl-hex-2-enyl]-5-fluoro-10,13-dimethyl-4,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one；(5R,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-5-fluoro-10,13-dimethyl-4,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
• CAS: 301699-56-9
• 化学式: C₂₉H₄₅FO
• 分子量: 428.674
• InChiKey: YCZYVOZQEKONED-TXUFYBMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (22E)-5-fluoro-5α-stigmasta-2,22-dien-6-one 在 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 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 216.0h， 以15%的产率得到(22R,23R)-5-fluoro-2α,3α,22,23-tetrahydroxy-5α-stigmastan-6-one
  参考文献：
  名称：

  Effects on Bioactivity due to C-5 Heteroatom Substituents on Synthetic 28-Homobrassinosteroid Analogs

  摘要：

  Five new 28-humobrassinosteroids have been synthesized, namely, (22R,23R)-5-fluoro-3 alpha,22,23-trihydroxy-5 alpha-stigmastan-6-one, (22R,23R)-5-fluoro-3 beta,22,23-trihydroxy-5 alpha-stigmastan-6-one (22R,23 R)-5-fluoro-2 alpha,3 alpha,22, 23-tetrahydroxy-5 alpha-stigmastan-6-one, (22R,23R)-3 alpha,5,21,23-tetrahydroxy-5 alpha-stigmastan-6-one and (22R,23R)-3 beta,5,22,23-tetrahydroxy-5 alpha-stigmastan-6-one. Their bioactivities were evaluated by the rice lamina inclination test. C-5 alpha Fluorinated analogs showed excellent in vitro bioactivity, also revealed at low doses, while C-5 alpha hydroxylated analogs resulted in an important decrease in bioactivity. Previously given explanations to justify the decreasing effect due to C-5 alpha electronegative groups should be revised. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00582-2
• 作为产物：
  描述：

  (22E)-5-fluoro-3β-hydroxy-5α-stigmast-22-en-6-one 在 吡啶 、 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (22E)-5-fluoro-5α-stigmasta-2,22-dien-6-one
  参考文献：
  名称：

  Effects on Bioactivity due to C-5 Heteroatom Substituents on Synthetic 28-Homobrassinosteroid Analogs

  摘要：

  Five new 28-humobrassinosteroids have been synthesized, namely, (22R,23R)-5-fluoro-3 alpha,22,23-trihydroxy-5 alpha-stigmastan-6-one, (22R,23R)-5-fluoro-3 beta,22,23-trihydroxy-5 alpha-stigmastan-6-one (22R,23 R)-5-fluoro-2 alpha,3 alpha,22, 23-tetrahydroxy-5 alpha-stigmastan-6-one, (22R,23R)-3 alpha,5,21,23-tetrahydroxy-5 alpha-stigmastan-6-one and (22R,23R)-3 beta,5,22,23-tetrahydroxy-5 alpha-stigmastan-6-one. Their bioactivities were evaluated by the rice lamina inclination test. C-5 alpha Fluorinated analogs showed excellent in vitro bioactivity, also revealed at low doses, while C-5 alpha hydroxylated analogs resulted in an important decrease in bioactivity. Previously given explanations to justify the decreasing effect due to C-5 alpha electronegative groups should be revised. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00582-2

文献信息

• Effects on Bioactivity due to C-5 Heteroatom Substituents on Synthetic 28-Homobrassinosteroid Analogs
  作者：J Ramírez

  DOI：10.1016/s0040-4020(00)00582-2

  日期：2000.8.18

  Five new 28-humobrassinosteroids have been synthesized, namely, (22R,23R)-5-fluoro-3 alpha,22,23-trihydroxy-5 alpha-stigmastan-6-one, (22R,23R)-5-fluoro-3 beta,22,23-trihydroxy-5 alpha-stigmastan-6-one (22R,23 R)-5-fluoro-2 alpha,3 alpha,22, 23-tetrahydroxy-5 alpha-stigmastan-6-one, (22R,23R)-3 alpha,5,21,23-tetrahydroxy-5 alpha-stigmastan-6-one and (22R,23R)-3 beta,5,22,23-tetrahydroxy-5 alpha-stigmastan-6-one. Their bioactivities were evaluated by the rice lamina inclination test. C-5 alpha Fluorinated analogs showed excellent in vitro bioactivity, also revealed at low doses, while C-5 alpha hydroxylated analogs resulted in an important decrease in bioactivity. Previously given explanations to justify the decreasing effect due to C-5 alpha electronegative groups should be revised. (C) 2000 Elsevier Science Ltd. All rights reserved.