17β-tert-butoxy-3'-methyl-(10αC19)-4,5-seco-androst-9(11)-eno[2,3-d]isoxazol-5-one | 67703-05-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 17β-tert-butoxy-3'-methyl-(10αC19)-4,5-seco-androst-9(11)-eno[2,3-d]isoxazol-5-one
• 英文别名: 17β-tert-butoxy-3'-methyl-(10αC¹⁹)-4,5-seco-androst-9(11)-eno[2,3-d]isoxazol-5-one
• CAS: 67703-05-3
• 化学式: C₂₅H₃₇NO₃
• 分子量: 399.574
• InChiKey: YBAOEDVSCXPUGM-OMLNERMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  52.33
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  17β-tert-butoxy-3'-methyl-(10αC19)-4,5-seco-androst-9(11)-eno[2,3-d]isoxazol-5-one 生成 (8S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-1,2,6,7,8,10,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one
  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：

  4-氯甲基-3,5-二甲基异噁唑 生成 17β-tert-butoxy-3'-methyl-(10αC19)-4,5-seco-androst-9(11)-eno[2,3-d]isoxazol-5-one
  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