(Z)-3-Methoxy-17-(2-oxazolin-4-ylidene)androsta-3,5-diene | 160192-05-2

• 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: (Z)-3-Methoxy-17-(2-oxazolin-4-ylidene)androsta-3,5-diene
• 英文别名: (4Z)-4-[(8R,9S,10R,13S,14S)-3-methoxy-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-ylidene]-1,3-oxazole
• CAS: 160192-05-2
• 化学式: C₂₃H₃₁NO₂
• 分子量: 353.505
• InChiKey: ZHJUWDFBRRPKSY-NYGJHTDRSA-N

物化性质

• 沸点：
  493.4±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-3-Methoxy-17-(2-oxazolin-4-ylidene)androsta-3,5-diene 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 70.0h， 以94%的产率得到去氧皮质酮
  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
• 作为产物：
  描述：

  17-<(E)-isocyano(tosyl)methylene>-3-methoxyandrosta-3,5-diene 在 氢氧化钾 、 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 66.0h， 生成 (Z)-3-Methoxy-17-(2-oxazolin-4-ylidene)androsta-3,5-diene
  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.