(25R)-3β,5-dihydroxy-5β-spirostan-6-one | 876908-20-2

• 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,5-dihydroxy-5β-spirostan-6-one
• 英文别名: (1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18S)-16,18-dihydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-19-one
• CAS: 876908-20-2
• 化学式: C₂₇H₄₂O₅
• 分子量: 446.627
• InChiKey: HCRGPOQBVFMZFY-PVJYNOIWSA-N

物化性质

• 熔点：
  212-214 °C(Solv: ethanol (64-17-5))
• 沸点：
  578.4±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (25R)-3β,5-dihydroxy-5β-spirostan-6-one 在 吡啶 、 高氯酸 、 lithium carbonate 、 间氯过氧苯甲酸 、 lithium bromide 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 28.0h， 生成 Anzurogenin A
  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 咪唑 、 氢氧化钾 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 (25R)-3β,5-dihydroxy-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

文献信息

• POLYHYDROXYSPIROSTANNONES AS PLANT GROWTH REGULATORS
  申请人：Coll Manchado, Francisco

  公开号：EP1020477A1

  公开（公告）日：2000-07-19

  This present invention is related with the biological chemical branch, and in particular with the preparation of new spirostanics analogues of brassinosteroids and with oxygenated functions in diferent positions of the A ring starting from sapogenins steroidals, through the performance of dihydroxylation reactions to a Δ2-steroid as principal reaction. The preparation of 6-oxo spirobrassinosteroids is described with oxygenated functions in positions 2 and 3 o 3 and 5, with the following general formula (2):    where: Compounds R1 R2 R3 2a CH3COO β CH3COO β H α 2b HO β CH3COO β H α 2c CH3COO β HO β H α 2d HO β HO β H α 2e HO β HO β H β 2f CH3COO β CH3COO β H β 2g CH3COO β CH3COO α H α 2h CH3COO β HO α H α 2i HO β HO α H α 2j HO β HO α H β 2k CH3COO β CH3COO α H β 2l CH3COO α CH3COO β H α 2m HO α HO β H α 2n HO α HO α H α 2ñ CH3COO α CH3COO α H α 2o H CH3COO β HO α 2p H HO β HO α 2q H HO β HO β 2r HO α HO α HO α 2s CH3COO α CH3COO α HO α These synthesized compounds present regulating activity of plant growth in very low concentrations, with wide perspectives for their use in Agriculture.

  本发明与生物化学分支有关，特别是以苷元类甾醇为原料，通过二羟基化反应，以Δ2-类甾醇为主要反应物，制备新的螺烷类黄铜甾醇类似物，并在 A 环的不同位置具有含氧功能。6-oxo 螺甾醇的制备方法如下：通式(2)为在 2、3 或 3、5 位置具有含氧功能的 6-oxo 螺甾醇： 其中 化合物 R1 R2 R3 2a CH3COO β CH3COO β H α 2b HO β CH3COO β H α 2c CH3COO β HO β H α 2d HO β HO β H α 2e HO β HO β H β 2f CH3COO β CH3COO β H β 2g CH3COO β CH3COO α H α 2h CH3COO β HO α H α 2i HO β HO α H α 2j HO β HO α H β 2k CH3COO β CH3COO α H β 2l CH3COO α CH3COO β H α 2m HO α HO β H α 2n HO α HO α H α 2ñ CH3COO α CH3COO α H α 2o H CH3COO β HO α 2p H HO β HO α 2q H HO β HO β 2r HO α HO α HO α 2s CH3COO α CH3COO α HO α 这些合成化合物在极低浓度下就具有调节植物生长的活性，在农业中具有广阔的应用前景。