2-{(S)-2-[6-Methoxycarbonyl-hex-(E)-ylidene]-3-oxo-cyclopentyl}-2-methyl-malonic acid dibenzyl ester | 207991-39-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-{(S)-2-[6-Methoxycarbonyl-hex-(E)-ylidene]-3-oxo-cyclopentyl}-2-methyl-malonic acid dibenzyl ester
• 英文别名: dibenzyl 2-[(1S,2E)-2-(7-methoxy-7-oxoheptylidene)-3-oxocyclopentyl]-2-methylpropanedioate
• CAS: 207991-39-7
• 化学式: C₃₁H₃₆O₇
• 分子量: 520.623
• InChiKey: GTBAFTIWNIOKPK-MMSVHKANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-{(S)-2-[6-Methoxycarbonyl-hex-(E)-ylidene]-3-oxo-cyclopentyl}-2-methyl-malonic acid dibenzyl ester 在 palladium on activated charcoal 吡啶 、 2,6-二甲基吡啶 、 lead(IV) acetate 、 三乙基硅烷 、 sodium tetrahydroborate 、 Wilkinson's catalyst 、 cerium(III) chloride 、 氢氟酸 、 氢气 、 四氯化钛 、 L-Selectride 、 potassium carbonate 、 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 42.67h， 生成 7-[(1R,2S,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-((E)-1-hydroxy-oct-2-enyl)-cyclopentyl]-heptanoic acid methyl 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：

  2-[(1S,2S)-2-(1-Hydroxy-6-methoxycarbonyl-hexyl)-3-oxo-cyclopentyl]-2-methyl-malonic acid dibenzyl ester 在 aluminum oxide 、 甲基磺酰氯 、 三乙胺 作用下， 生成 2-{(S)-2-[6-Methoxycarbonyl-hex-(E)-ylidene]-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