(22β)-3β-acetoxyfurost-5-ene | 695226-19-8

• 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: (22β)-3β-acetoxyfurost-5-ene
• 英文别名: [(1S,2S,4S,6R,7S,8R,9S,12S,13R,16S)-7,9,13-trimethyl-6-(3-methylbutyl)-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-en-16-yl] acetate
• CAS: 695226-19-8
• 化学式: C₂₉H₄₆O₃
• 分子量: 442.682
• InChiKey: NHSDBYPDTXRDFQ-OHEQKHDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (22β)-3β-acetoxyfurost-5-ene 在 potassium dichromate 、 高氯酸 、 乙酸酐 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 11.5h， 生成 3β-acetoxycholesta-5,17(20)-diene-16,22-dione
  参考文献：
  名称：

  A Novel Synthetic Approach from Diosgenin to a 17α‐Hydroxy Orthoester via a Regio‐ and Stereo‐Specific Rearrangement of an Epoxy Ester

  摘要：

  A cholesterol model compound, containing 16beta-acetoxy, 17alpha-hydroxy, and (20S, 22R)-epoxy groups was synthesized from diosgenin in 13 steps and was rearranged regio- and stereo-specifically to an orthoester with BF3.Et2O.

  DOI：

  10.1081/scc-120028627
• 作为产物：
  描述：

  薯蓣皂素 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 55.0h， 生成 (22β)-3β-acetoxyfurost-5-ene
  参考文献：
  名称：

  A Novel Synthetic Approach from Diosgenin to a 17α‐Hydroxy Orthoester via a Regio‐ and Stereo‐Specific Rearrangement of an Epoxy Ester

  摘要：

  A cholesterol model compound, containing 16beta-acetoxy, 17alpha-hydroxy, and (20S, 22R)-epoxy groups was synthesized from diosgenin in 13 steps and was rearranged regio- and stereo-specifically to an orthoester with BF3.Et2O.

  DOI：

  10.1081/scc-120028627

文献信息

• A rapid and simple one-pot procedure for the synthesis of 3β-acetoxy-5α-hydroxy-6-oxo steroids
  作者：Anielka Rosado-Abón、Margarita Romero-Ávila、Martin A. Iglesias-Arteaga

  DOI：10.3998/ark.5550190.0011.a10

  日期：——

  A fast one-pot procedure for the synthesis of 5α-hydroxy-6-oxo steroids is described. Epoxidation of 3β-hydoxy-∆ steroids followed by oxidative cleavage of the resulting epoxide with aqueous CrO3 lead to the desired compounds without affection of labile side chains.

  描述了一种用于合成 5α-羟基-6-氧代类固醇的快速一锅法。3β-羟基-Δ 类固醇的环氧化，然后用 CrO3 水溶液氧化裂解所得环氧化物，生成所需的化合物，而不会影响不稳定的侧链。
• Synthesis and biological activity of furostanic analogues of brassinosteroids bearing the 5α-hydroxy-6-oxo moiety
  作者：Margarita Romero-Avila、Guadalupe de Dios-Bravo、Jóse M. Mendez-Stivalet、Rogelio Rodríguez-Sotres、Martin A. Iglesias-Arteaga

  DOI：10.1016/j.steroids.2007.08.007

  日期：2007.12

  Two furostanic analogues of brassinosteroids bearing the 5 alpha-hydroxy-6-oxo moiety were synthesized and their biological activity studied using the bean second internode elongation test. one of the compounds produced significant stimulation at doses of 2.5 and 5 ng/plant. (c) 2007 Elsevier Inc. All rights reserved.