3β-hydroxy-5α,6α-epoxy-17(13→18)-abeo-pregna-13,15,17-trien-20-one | 1441306-90-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3β-hydroxy-5α,6α-epoxy-17(13→18)-abeo-pregna-13,15,17-trien-20-one
• 英文别名: salpichrolide B；1-[(1S,2R,5S,7R,9S,11R)-5-hydroxy-2-methyl-8-oxapentacyclo[9.8.0.02,7.07,9.012,17]nonadeca-12(17),13,15-trien-15-yl]ethanone
• CAS: 1441306-90-6
• 化学式: C₂₁H₂₆O₃
• 分子量: 326.436
• InChiKey: USRJRHYIPVIWNS-IHLDHJRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3β-hydroxy-17(13→18)-abeo-pregna-5,13,15,17-tetraen-20-one 在 sodium carbonate 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 水 为溶剂， 反应 2.0h， 生成 3β-hydroxy-5α,6α-epoxy-17(13→18)-abeo-pregna-13,15,17-trien-20-one 、 3β-hydroxy-5β,6β-epoxy-17(1318)-abeo-pregna-13,15,17-trien-20-one
  参考文献：
  名称：

  Synthesis and antifungal activity of C-21 steroids with an aromatic D ring

  摘要：

  Six analogues of salpichrolides with a simplified side chain (6-11) were synthesized using a new methodology to obtain steroids with an aromatic D-ring. The key step was the elimination of HBr in a vicinal dibromo D-homosteroid by treatment with 1,4-diazabicyclo[2.2.2]octane (DABCO). All new compounds were completely characterized by 2D NMR techniques and tested on two fungal pathogenic species, Fusarium virguliforme and Fusarium solani. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2013.02.003

文献信息

• Synthesis and antifungal activity of C-21 steroids with an aromatic D ring
  作者：Juan M. Sonego、Adriana M. Cirigliano、Gabriela M. Cabrera、Gerardo Burton、Adriana S. Veleiro

  DOI：10.1016/j.steroids.2013.02.003

  日期：2013.7

  Six analogues of salpichrolides with a simplified side chain (6-11) were synthesized using a new methodology to obtain steroids with an aromatic D-ring. The key step was the elimination of HBr in a vicinal dibromo D-homosteroid by treatment with 1,4-diazabicyclo[2.2.2]octane (DABCO). All new compounds were completely characterized by 2D NMR techniques and tested on two fungal pathogenic species, Fusarium virguliforme and Fusarium solani. (C) 2013 Elsevier Inc. All rights reserved.