3β,22-dihydroxy-23,24-dinorchol-4-ene | 634894-19-2

• 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: 3β,22-dihydroxy-23,24-dinorchol-4-ene
• 英文别名: (3S,8S,9S,10R,13S,14S,17R)-17-[(2S)-1-hydroxypropan-2-yl]-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 634894-19-2
• 化学式: C₂₂H₃₆O₂
• 分子量: 332.527
• InChiKey: KNPRREBOTYKWPM-NBOCEFNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3β,22-dihydroxy-23,24-dinorchol-4-ene 在 吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 63.08h， 生成 chol-4-en-23-yn-3-one
  参考文献：
  名称：

  Synthesis of 3β,6α-dihydroxy-5α-cholan-23-one

  摘要：

  Evidence for the presence of 3beta,6alpha-dihydroxy-5alpha-chol-9(11)-en-23-one in the aglycone mixture from the starfish Marthasterias glacialis is provided by the synthesis of 3beta,6alpha-dihydroxy-5alpha-cholan-23-one (19) and its identification in the hydrogenated aglycone mixture. The side-chain is constructed from the 23,24-dinorcholanol (13) by reaction of the 22-tosylate (16) with the acetylide anion, followed by hydration of the resulting 23-yne (17). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.08.020
• 作为产物：
  描述：

  二去甲胆烯醛 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以66%的产率得到3β,22-dihydroxy-23,24-dinorchol-4-ene
  参考文献：
  名称：

  Synthesis of 3β,6α-dihydroxy-5α-cholan-23-one

  摘要：

  Evidence for the presence of 3beta,6alpha-dihydroxy-5alpha-chol-9(11)-en-23-one in the aglycone mixture from the starfish Marthasterias glacialis is provided by the synthesis of 3beta,6alpha-dihydroxy-5alpha-cholan-23-one (19) and its identification in the hydrogenated aglycone mixture. The side-chain is constructed from the 23,24-dinorcholanol (13) by reaction of the 22-tosylate (16) with the acetylide anion, followed by hydration of the resulting 23-yne (17). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.08.020

文献信息

• The first example of lipase-catalyzed resolution of a stereogenic center in steroid side chains by transesterification in organic solvent
  作者：Patrizia Ferraboschi、Antonella Molatore、Elisa Verza、Enzo Santaniello

  DOI：10.1016/0957-4166(96)00178-4

  日期：1996.6

  The Pseudomonas cepacia lipase selectively catalyzes the acylation of the (20S)-isomer of the 22-alcohol group in the C-22 steroid compounds 1a and 4a when the transesterification is irreversibly carried out with vinyl acetate in an organic solvent.

  的洋葱假单胞菌脂肪酶选择性催化（20S）的酰化的C-22类固醇化合物的22-醇基团的异构体1A和4A时，酯交换反应与乙酸乙烯酯在有机溶剂中不可逆地进行。
• Synthesis of 3β,6α-dihydroxy-5α-cholan-23-one
  作者：Lutfun Nahar、Alan B Turner

  DOI：10.1016/j.tet.2003.08.020

  日期：2003.10

  Evidence for the presence of 3beta,6alpha-dihydroxy-5alpha-chol-9(11)-en-23-one in the aglycone mixture from the starfish Marthasterias glacialis is provided by the synthesis of 3beta,6alpha-dihydroxy-5alpha-cholan-23-one (19) and its identification in the hydrogenated aglycone mixture. The side-chain is constructed from the 23,24-dinorcholanol (13) by reaction of the 22-tosylate (16) with the acetylide anion, followed by hydration of the resulting 23-yne (17). (C) 2003 Elsevier Ltd. All rights reserved.