3,20-Dioxopregna-4,9(11),16-trien-21-yl formate | 160191-98-0

• 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: 3,20-Dioxopregna-4,9(11),16-trien-21-yl formate
• 英文别名: [2-[(8S,10S,13S,14S)-10,13-dimethyl-3-oxo-1,2,6,7,8,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] formate
• CAS: 160191-98-0
• 化学式: C₂₂H₂₆O₄
• 分子量: 354.446
• InChiKey: MZIAGXTWYIIGGL-FHQLIMNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,20-Dioxopregna-4,9(11),16-trien-21-yl formate 在 盐酸 、 potassium permanganate 、 甲酸 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 0.01h， 生成 16α,17,21-trihydroxypregna-4,9(11)-diene-3,20-dione
  参考文献：
  名称：

  Synthesis of Triamcinolone Acetonide from 9-Hydroxy-3-methoxy-17-(2-methoxy-3-oxazolin-4-yl)androsta-3,5,16-triene

  摘要：

  DOI：

  10.1021/jo00103a063
• 作为产物：
  描述：

  (E)-17-(isocyanotosylmethylene)-3-methoxyandrosta-3,5,9(11)-triene 在 苄基三乙基氯化铵 sodium hydroxide 作用下， 以 水 、 苯 为溶剂， 反应 5.0h， 生成 3,20-Dioxopregna-4,9(11),16-trien-21-yl formate
  参考文献：
  名称：

  Synthesis of 17-(2-Methoxy-3-oxazolin-4-yl)-, 17-(3-Oxazolin-4-yl)-, and 17-(2-Oxazolin-4-ylidene) Substituted Steroids and Their Use as Precursors of Corticosteroids

  摘要：

  17-(Isocyanotosylmethylene)steroids 4 are useful intermediates in the conversion of 17-oxosteroids into 17-(hydroxyacetyl)steroids. The 21-CH2OH group is effectively introduced by a base-mediated reaction of compounds 4 with formaldehyde and MeOH to give 17-(2-methoxy-3-oxazolin-4-yl) derivatives 12, which by acid hydrolysis give 17-(hydroxyacetyl)steroids 10 and 16 in high yields. Partial hydrolysis of the same oxazoline derivatives 12 provides the 17-(hydroxyacetyl) cortico side chain of 13 equipped with a formyl-protected hydroxy group. 3-Oxazolinyl and 2-oxazolinylidene steroid derivatives 19, 20, and 21, without a 2-methoxy substituent, are discussed as alternatives of 12.

  DOI：

  10.1021/jo00098a024

文献信息

• Synthesis of 17-(2-Methoxy-3-oxazolin-4-yl)-, 17-(3-Oxazolin-4-yl)-, and 17-(2-Oxazolin-4-ylidene) Substituted Steroids and Their Use as Precursors of Corticosteroids
  作者：Daan van Leusen、Jacobus N. M. Batist、Jia Lei、Erik van Echten、Antoon C. Brouwer、Albert M. van Leusen

  DOI：10.1021/jo00098a024

  日期：1994.9

  17-(Isocyanotosylmethylene)steroids 4 are useful intermediates in the conversion of 17-oxosteroids into 17-(hydroxyacetyl)steroids. The 21-CH2OH group is effectively introduced by a base-mediated reaction of compounds 4 with formaldehyde and MeOH to give 17-(2-methoxy-3-oxazolin-4-yl) derivatives 12, which by acid hydrolysis give 17-(hydroxyacetyl)steroids 10 and 16 in high yields. Partial hydrolysis of the same oxazoline derivatives 12 provides the 17-(hydroxyacetyl) cortico side chain of 13 equipped with a formyl-protected hydroxy group. 3-Oxazolinyl and 2-oxazolinylidene steroid derivatives 19, 20, and 21, without a 2-methoxy substituent, are discussed as alternatives of 12.
• Synthesis of Triamcinolone Acetonide from 9-Hydroxy-3-methoxy-17-(2-methoxy-3-oxazolin-4-yl)androsta-3,5,16-triene
  作者：Daan van Leusen、Albert M. van Leusen

  DOI：10.1021/jo00103a063

  日期：1994.12