2-{(1S,2S)-2-[1-(Imidazole-1-carbothioyloxy)-6-methoxycarbonyl-hexyl]-3-oxo-cyclopentyl}-2-methyl-malonic acid dibenzyl ester | 207991-54-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-{(1S,2S)-2-[1-(Imidazole-1-carbothioyloxy)-6-methoxycarbonyl-hexyl]-3-oxo-cyclopentyl}-2-methyl-malonic acid dibenzyl ester
• 英文别名: dibenzyl 2-[(1S,2S)-2-[1-(imidazole-1-carbothioyloxy)-7-methoxy-7-oxoheptyl]-3-oxocyclopentyl]-2-methylpropanedioate
• CAS: 207991-54-6
• 化学式: C₃₅H₄₀N₂O₈S
• 分子量: 648.777
• InChiKey: RBRZGXHLABLDOH-ONMBETLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  46
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  155
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-{(1S,2S)-2-[1-(Imidazole-1-carbothioyloxy)-6-methoxycarbonyl-hexyl]-3-oxo-cyclopentyl}-2-methyl-malonic acid dibenzyl ester 在 二叔丁基过氧化物 、 三正丁基氢锡 作用下， 以46%的产率得到2-[(1S,2R)-2-(6-Methoxycarbonyl-hexyl)-3-oxo-cyclopentyl]-2-methyl-malonic acid dibenzyl ester
  参考文献：
  名称：

  A Catalytic Asymmetric Synthesis of 11-Deoxy-PGF_1α Using ALB, a Heterobimetallic Multifunctional Asymmetric Complex

  摘要：

  A catalytic asymmetric synthesis of 11-deoxy-PGF(1 alpha) has been achieved using a cascade Michael-aldol reaction as a key step. This cascade reaction was efficiently promoted by a catalytic use of AlLibis[(S)-binaphthoxide] complex (ALB) to give the three-component coupling product at room temperature in 92% ee and in 84% yield. The three-component coupling product was then converted to (+)-11-deoxy-PGF(1 alpha) through several steps, including an oxidative decarboxylation, an aldol reaction, and a Wharton reaction. Moreover, the racemic enone, 20 was transformed into 21, the three-component coupling product, a potential intermediate for PGF(1 alpha), in 97% ee and in 75% yield through catalytic kinetic resolution.

  DOI：

  10.1021/jo9723319
• 作为产物：
  描述：

  N,N'-硫羰基二咪唑 、 2-[(1S,2S)-2-(1-Hydroxy-6-methoxycarbonyl-hexyl)-3-oxo-cyclopentyl]-2-methyl-malonic acid dibenzyl ester 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 以53%的产率得到2-{(1S,2S)-2-[1-(Imidazole-1-carbothioyloxy)-6-methoxycarbonyl-hexyl]-3-oxo-cyclopentyl}-2-methyl-malonic acid dibenzyl ester
  参考文献：
  名称：

  A Catalytic Asymmetric Synthesis of 11-Deoxy-PGF_1α Using ALB, a Heterobimetallic Multifunctional Asymmetric Complex

  摘要：

  A catalytic asymmetric synthesis of 11-deoxy-PGF(1 alpha) has been achieved using a cascade Michael-aldol reaction as a key step. This cascade reaction was efficiently promoted by a catalytic use of AlLibis[(S)-binaphthoxide] complex (ALB) to give the three-component coupling product at room temperature in 92% ee and in 84% yield. The three-component coupling product was then converted to (+)-11-deoxy-PGF(1 alpha) through several steps, including an oxidative decarboxylation, an aldol reaction, and a Wharton reaction. Moreover, the racemic enone, 20 was transformed into 21, the three-component coupling product, a potential intermediate for PGF(1 alpha), in 97% ee and in 75% yield through catalytic kinetic resolution.

  DOI：

  10.1021/jo9723319