11α-Mesyloxy-progesteron | 10116-24-2

• 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: 11α-Mesyloxy-progesteron
• 英文别名: 11α-methanesulfonyloxy-pregn-4-ene-3,20-dione；11α-Methansulfonyloxy-pregn-4-en-3,20-dion；11α-mesyloxy-progesterone；[(8S,9S,10R,11R,13S,14S,17S)-17-acetyl-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-11-yl] methanesulfonate
• CAS: 10116-24-2
• 化学式: C₂₂H₃₂O₅S
• 分子量: 408.559
• InChiKey: QGSNTGRNDLYUPN-QSZFMGJTSA-N

物化性质

• 熔点：
  165-167 °C
• 沸点：
  577.9±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  85.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  11α-Mesyloxy-progesteron 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 生成 孕甾-4,11-二烯-3,20-二酮
  参考文献：
  名称：

  甾族合成中间体BCD-三环9-en-5-ones的C（10）-甲基化。

  摘要：

  AbstractA literature survey indicated that stereospecific non‐reductive β‐face methylation at C(10) of steroidal synthesis intermediate BCD‐tricyclic 9‐en‐5‐ones had never been effected. An attempt to define the factors controlling the β/α product ratio in such alkylations was made. The course of methylation is significantly affected by the temperature. In the best case, methylation of the sodium enolate of 17 β‐t‐butoxy‐19‐(3,5‐dimethyl‐4‐isoxazolyl)‐deA‐androst‐9‐en‐5‐one (18) in tetrahydrofuran at − 78° gave a β/α product ratio of > 5:1. The reaction mixture contained no unalkylated or dialkylated materials, indicating that enolate exchange probably did not occur at this temperature. The 10β‐methylated product 23, isolated in 78% yield, was converted to Δ9(ll)‐dehydrotestosterone (29). Compounds 23 and 29 are potential intermediates for the synthesis of 11‐oxygenated steroids.

  DOI：

  10.1002/hlca.19740570433
• 作为产物：
  描述：

  11Alpha-孕酮 、 甲基磺酰氯 以 吡啶 为溶剂， 生成 11α-Mesyloxy-progesteron
  参考文献：
  名称：

  11-Substituted-desA-pregnanes and derivatives thereof

  摘要：

  这项发明涉及11-取代-去氢孕甾烷及其衍生物，可作为孕甾系列9-β，10-α-已知类固醇的中间体。这些后者化合物可用作孕激素和保钠剂。

  公开号：

  US03956316A1

文献信息

• 11-Substituted-desA-pregnanes and derivatives thereof
  申请人：Hoffmann-La Roche Inc.

  公开号：US03956316A1

  公开（公告）日：1976-05-11

  This invention is directed to 11-substituted-desA-pregnanes and derivatives thereof which are useful as intermediates in the production of 9.beta.,10.alpha.-known steroids of the pregnane series. These latter compounds can be utilized as progestational and salt-retaining agents.

  这项发明涉及11-取代-去氢孕甾烷及其衍生物，可作为孕甾系列9-β，10-α-已知类固醇的中间体。这些后者化合物可用作孕激素和保钠剂。
• US3956316A
  申请人：——

  公开号：US3956316A

  公开（公告）日：1976-05-11
• Chloromethanesulfonate as an Efficient Leaving Group: Rearrangement of the Carbon-Carbon Bond and Conversion of Alcohols into Azides and Nitriles
  作者：Takeshi Shimizu

  DOI：10.1055/s-1999-3541

  日期：1999.8
• C(10)-Methylation of Steroidal Synthesis Intermediate BCD-Tricyclic 9-En-5-ones
  作者：John W. Scott、Paul Buchschacher、Ludwik Labler、Werner Meier、Andor Fürst

  DOI：10.1002/hlca.19740570433

  日期：1974.4.27

  AbstractA literature survey indicated that stereospecific non‐reductive β‐face methylation at C(10) of steroidal synthesis intermediate BCD‐tricyclic 9‐en‐5‐ones had never been effected. An attempt to define the factors controlling the β/α product ratio in such alkylations was made. The course of methylation is significantly affected by the temperature. In the best case, methylation of the sodium enolate of 17 β‐t‐butoxy‐19‐(3,5‐dimethyl‐4‐isoxazolyl)‐deA‐androst‐9‐en‐5‐one (18) in tetrahydrofuran at − 78° gave a β/α product ratio of > 5:1. The reaction mixture contained no unalkylated or dialkylated materials, indicating that enolate exchange probably did not occur at this temperature. The 10β‐methylated product 23, isolated in 78% yield, was converted to Δ9(ll)‐dehydrotestosterone (29). Compounds 23 and 29 are potential intermediates for the synthesis of 11‐oxygenated steroids.