7-[(1R,2S,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-((E)-oct-2-enoyl)-cyclopentyl]-heptanoic acid methyl ester | 207991-44-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 7-[(1R,2S,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-((E)-oct-2-enoyl)-cyclopentyl]-heptanoic acid methyl ester
• 英文别名: methyl 7-[(1R,2S,5S)-2-[tert-butyl(dimethyl)silyl]oxy-5-[(E)-oct-2-enoyl]cyclopentyl]heptanoate
• CAS: 207991-44-4
• 化学式: C₂₇H₅₀O₄Si
• 分子量: 466.777
• InChiKey: YXXVXRMQZAPJFI-LBTVTJJZSA-N

物化性质

• 沸点：
  504.494±35.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  0.955±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.62
• 重原子数：
  32
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-[(1R,2S,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-((E)-oct-2-enoyl)-cyclopentyl]-heptanoic acid methyl ester 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 8.75h， 生成 7-[(1R,2S,5S)-2-((E)-(S)-1-Acetoxy-oct-2-enyl)-5-(tert-butyl-dimethyl-silanyloxy)-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 palladium on activated charcoal 吡啶 、 2,6-二甲基吡啶 、 lead(IV) acetate 、 4-二甲氨基吡啶 、 二叔丁基过氧化物 、 氢气 、 三正丁基氢锡 、 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 、 二氯甲烷 、 乙腈 为溶剂， 反应 29.17h， 生成 7-[(1R,2S,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-((E)-oct-2-enoyl)-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