5-(3,5-dimethyl-isoxazol-4-yl)-3-oxo-pentanoic acid methyl ester | 53655-59-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 5-(3,5-dimethyl-isoxazol-4-yl)-3-oxo-pentanoic acid methyl ester
• 英文别名: methyl 5-(3,5-dimethyl-1,2-oxazol-4-yl)-3-oxopentanoate
• CAS: 53655-59-7
• 化学式: C₁₁H₁₅NO₄
• 分子量: 225.244
• InChiKey: RXLHEAXGEVPFMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(3,5-dimethyl-isoxazol-4-yl)-3-oxo-pentanoic acid methyl ester 生成 17β-acetoxy-3'-methyl-4,5-seco-estr-9-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
• 作为产物：
  描述：

  4-氯甲基-3,5-二甲基异噁唑 、 乙酰乙酸甲酯 生成 5-(3,5-dimethyl-isoxazol-4-yl)-3-oxo-pentanoic acid methyl ester
  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

文献信息

• 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.