24-oxocholesterol i-methyl ether | 66551-23-3

• 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: 24-oxocholesterol i-methyl ether
• 英文别名: (6R)-6-[(1S,2R,5S,7R,8R,10S,11S,14R,15R)-8-methoxy-2,15-dimethyl-14-pentacyclo[8.7.0.02,7.05,7.011,15]heptadecanyl]-2-methylheptan-3-one
• CAS: 66551-23-3
• 化学式: C₂₈H₄₆O₂
• 分子量: 414.672
• InChiKey: ZTJCVLFLRBQSKY-IXBCKJOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (24ξ)-24-vinylcholesterol i-methyl ether 在 potassium permanganate 、 sodium periodate 、 sodium phosphate buffer 作用下， 以 叔丁醇 为溶剂， 反应 76.0h， 以1.8 mg的产率得到5-cholenic acid i-methyl ether
  参考文献：
  名称：

  Biosynthetic studies of marine lipids. 31. Evidence for a protonated cyclopropyl intermediate in the biosynthesis of 24-propylidenecholesterol

  摘要：

  The biosynthesis of 24-propylidenecholesterol (11-N) was determined by the use of cell-free extracts from the Chrysophyte alga Chrysoderma mucosa. The biosynthetic sequence was shown to proceed via desmosterol (28-N), 24-methylenecholesterol (29-N), and isofucosterol (30-N) to 24-propylidenecholesterol (11-N). 24-Vinylcholesterol (13-N) was neither a substrate nor a product of the S-adenosylmethionine (SAM)-methyltransferase, nor was it detected in cultures grown in the presence of azasterol inhibitors. Chemical degradation of 24-propylidenecholesterol (11-N) from enzymatic [H-3]SAM methylation of isofucosterol (30-N) provided evidence for the protonated cyclopropane intermediate (27-N). The mechanism involving such an intermediate is consistent with the structures and stereochemical assignments of trace sterols found in this alga. Evidence for the intermediacy of protonated cyclopropanes in the SAM sterol methyl-transfer reactions leading to isofucosterol (30-N), fucosterol (31-N), and 24-methylenecholesterol (29-N) could not be found.

  DOI：

  10.1021/ja00004a047

文献信息

• Process for producing steroid compounds having an oxogroup in the side chain
  申请人：TEIJIN LIMITED

  公开号：EP0013082A1

  公开（公告）日：1980-07-09

  A process for producing a steroid compound having an oxo group in the side chain, which comprises condensing an acid halide having a steroid skeleton with an organozinc compound at a halocarbonyl group of the acid halide in an inert organic medium in the presence of a catalytic amound of an ether capable of forming a complex with the organozinc compound and, if desired, hydrolyzing the product. The process gives the steroid compound in a high yield, and often in an almost quantitative yield. The steroid compound can be an important intermediate for the production of vitamin D3 analogs, such as active forms of vitamin D3.

  一种生产侧链中含有氧代基团的甾体化合物的工艺，包括在惰性有机介质中，在能与有机锌化合物形成络合物的醚的催化下，在酸卤化物的卤代羰基上将具有甾体骨架的酸卤化物与有机锌化合物缩合，并在需要时水解产物。该工艺可以得到高产率的甾体化合物，通常几乎可以达到定量产率。类固醇化合物可以作为生产维生素 D3 类似物（如活性维生素 D3）的重要中间体。
• US4298537A
  申请人：——

  公开号：US4298537A

  公开（公告）日：1981-11-03
• Biosynthetic studies of marine lipids. 31. Evidence for a protonated cyclopropyl intermediate in the biosynthesis of 24-propylidenecholesterol
  作者：Jose Luis Giner、Carl Djerassi

  DOI：10.1021/ja00004a047

  日期：1991.2

  The biosynthesis of 24-propylidenecholesterol (11-N) was determined by the use of cell-free extracts from the Chrysophyte alga Chrysoderma mucosa. The biosynthetic sequence was shown to proceed via desmosterol (28-N), 24-methylenecholesterol (29-N), and isofucosterol (30-N) to 24-propylidenecholesterol (11-N). 24-Vinylcholesterol (13-N) was neither a substrate nor a product of the S-adenosylmethionine (SAM)-methyltransferase, nor was it detected in cultures grown in the presence of azasterol inhibitors. Chemical degradation of 24-propylidenecholesterol (11-N) from enzymatic [H-3]SAM methylation of isofucosterol (30-N) provided evidence for the protonated cyclopropane intermediate (27-N). The mechanism involving such an intermediate is consistent with the structures and stereochemical assignments of trace sterols found in this alga. Evidence for the intermediacy of protonated cyclopropanes in the SAM sterol methyl-transfer reactions leading to isofucosterol (30-N), fucosterol (31-N), and 24-methylenecholesterol (29-N) could not be found.