3-[(8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-(3E)-ylideneaminooxy]-propionic acid methyl ester | 175026-69-4

• 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: 3-[(8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-(3E)-ylideneaminooxy]-propionic acid methyl ester
• CAS: 175026-69-4
• 化学式: C₂₃H₃₅NO₄
• 分子量: 389.535
• InChiKey: RDQGAGLFSXTSLA-FQVLHXRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  68.12
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-[(8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-(3E)-ylideneaminooxy]-propionic acid methyl ester 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.17h， 以91%的产率得到3-[(8R,9S,10R,13S,14S)-10,13-Dimethyl-17-oxo-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-(3E)-ylideneaminooxy]-propionic acid methyl ester
  参考文献：
  名称：

  Preparation and properties of 3-(O-(2-carboxyethyl))oxime derivatives of steroid hormones

  摘要：

  Minerals of 3E and 3Z isomers of 3-(O-(2-carboxyethyl))oxime (CEO) derivatives of testosterone and 17 alpha-methyltestosterone were prepared by reaction with (O-(2-carboxyethyl))hydroxylamine. These isomers Mere separated after conversion into methyl esters, and mild alkaline hydrolysis recovered pure E/Z-isomers of 3-CEO derivatives of testosterone and 17 alpha-methyltestosterone. By the same method, after oximation, methylation, and separation, (20R)-20-hydroxypregn-4-en-3-one gave (3E,20R)-20-hydroxgpregn-4-en-3-one, 3(O-(2-carboxyethyl))oxime and (3Z,20R)-20-hydroxypregn-4-en-3-one 3-(O-(2-carboxyerhyl))oxime methyl esters. The oxidation and subsequent hydrolysis of these compounds produced 3E and 3Z isomers of the 3-CEO derivative of progesterone. Pure E/Z-isomers of 3-CEO derivatives are designed for the development of immunoanalytical systems, which make use of the bridge heterology based on the geometric isomerism.

  DOI：

  10.1016/0039-128x(95)00198-y
• 作为产物：
  描述：

  3-[(8R,9S,10R,13S,14S)-10,13-Dimethyl-17-oxo-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-(3E)-ylideneaminooxy]-propionic acid methyl ester 在 lithium tri(t-butoxy)aluminum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以68%的产率得到3-[(8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-(3E)-ylideneaminooxy]-propionic acid methyl ester
  参考文献：
  名称：

  Preparation and properties of 3-(O-(2-carboxyethyl))oxime derivatives of steroid hormones

  摘要：

  Minerals of 3E and 3Z isomers of 3-(O-(2-carboxyethyl))oxime (CEO) derivatives of testosterone and 17 alpha-methyltestosterone were prepared by reaction with (O-(2-carboxyethyl))hydroxylamine. These isomers Mere separated after conversion into methyl esters, and mild alkaline hydrolysis recovered pure E/Z-isomers of 3-CEO derivatives of testosterone and 17 alpha-methyltestosterone. By the same method, after oximation, methylation, and separation, (20R)-20-hydroxypregn-4-en-3-one gave (3E,20R)-20-hydroxgpregn-4-en-3-one, 3(O-(2-carboxyethyl))oxime and (3Z,20R)-20-hydroxypregn-4-en-3-one 3-(O-(2-carboxyerhyl))oxime methyl esters. The oxidation and subsequent hydrolysis of these compounds produced 3E and 3Z isomers of the 3-CEO derivative of progesterone. Pure E/Z-isomers of 3-CEO derivatives are designed for the development of immunoanalytical systems, which make use of the bridge heterology based on the geometric isomerism.

  DOI：

  10.1016/0039-128x(95)00198-y