(25R)-5-hydroxy-5β-spirost-2-en-6-one | 200353-19-1

• 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: (25R)-5-hydroxy-5β-spirost-2-en-6-one
• 英文别名: (25R)-5beta-hydroxy-spirost-2-en-6-one；(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,18S)-18-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-15-ene-6,2'-oxane]-19-one
• CAS: 200353-19-1
• 化学式: C₂₇H₄₀O₄
• 分子量: 428.612
• InChiKey: LDLYRDIDWAPGIF-BSFGPSEKSA-N

物化性质

• 熔点：
  189-192 °C(Solv: acetone (67-64-1))
• 沸点：
  546.0±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  31
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (25R)-5-hydroxy-5β-spirost-2-en-6-one 在 四氧化锇 、 N-甲基吲哚酮 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 24.0h， 以68%的产率得到(25R)-2β,3β,5-trihydroxy-5β-spirostan-6-one
  参考文献：
  名称：

  Novel 5β-hydroxyspirostan-6-ones ecdysteroid antagonists: Synthesis and biological testing

  摘要：

  Eight new 5 beta-hydroxy-spirostan-6-ones bearing hydroxy and amino functions in the A ring, i.e., 3 beta-OH, 3 alpha-OH, 2 beta,3 beta-OH, 2 alpha,3 beta-OH, 3 beta-NH2, 2 alpha-NH2-3 beta-OH, 2 beta-NH2-3 beta-OH, and 2 beta-OH-3 beta-NH2, were efficiently synthesized, and their antiecdysteroid activities were evaluated on the metamorphosis bioassay of mosquito Aedes aegypti. To our knowledge, these new steroids represent the first 5 beta-hydroxy-spirostanes which have been tested for antiecdysteroid activity in mosquitoes. The higher antagonistic effect was found for compounds bearing the 3 beta-hydroxy and 2 beta,3 beta-dihydroxy functionality which show promise as environmental friendly insecticides. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.02.024
• 作为产物：
  描述：

  (25R)-3β,5-dihydroxy-5β-spirostan-6-one 在 吡啶 、 lithium carbonate 、 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 (25R)-5-hydroxy-5β-spirost-2-en-6-one
  参考文献：
  名称：

  Novel 5β-hydroxyspirostan-6-ones ecdysteroid antagonists: Synthesis and biological testing

  摘要：

  Eight new 5 beta-hydroxy-spirostan-6-ones bearing hydroxy and amino functions in the A ring, i.e., 3 beta-OH, 3 alpha-OH, 2 beta,3 beta-OH, 2 alpha,3 beta-OH, 3 beta-NH2, 2 alpha-NH2-3 beta-OH, 2 beta-NH2-3 beta-OH, and 2 beta-OH-3 beta-NH2, were efficiently synthesized, and their antiecdysteroid activities were evaluated on the metamorphosis bioassay of mosquito Aedes aegypti. To our knowledge, these new steroids represent the first 5 beta-hydroxy-spirostanes which have been tested for antiecdysteroid activity in mosquitoes. The higher antagonistic effect was found for compounds bearing the 3 beta-hydroxy and 2 beta,3 beta-dihydroxy functionality which show promise as environmental friendly insecticides. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.02.024

文献信息

• Rivera, Daniel G.; Pando, Orlando; Leliebre-Lara, Vivian, Journal of Chemical Research, 2004, # 1, p. 53 - 54
  作者：Rivera, Daniel G.、Pando, Orlando、Leliebre-Lara, Vivian、Coll, Deysma、Leon, Fredy、Coll, Francisco

  DOI：——

  日期：——