(25R)-3β-(t-butoxycarbonylamino)-5-hydroxy-5α-spirostan-6-one | 876908-29-1

• 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)-3β-(t-butoxycarbonylamino)-5-hydroxy-5α-spirostan-6-one
• CAS: 876908-29-1
• 化学式: C₃₂H₅₁NO₆
• 分子量: 545.76
• InChiKey: UTBRHMZJLGEVDK-JMOSEUNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.62
• 重原子数：
  39.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  94.09
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (25R)-3β-(t-butoxycarbonylamino)-5-hydroxy-5α-spirostan-6-one 在 氢氧化钾 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 26.17h， 生成 (25R)-3β-amino-5-hydroxy-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)-spirostan-22α-O-3β,5α,6β-triol 在 Lindlar's catalyst 咪唑 、 sodium azide 、 偶氮二甲酸二异丙酯 、 氢气 、 三乙胺 、 三苯基膦 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 137.0h， 生成 (25R)-3β-(t-butoxycarbonylamino)-5-hydroxy-5α-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