(R)-4-(tert-Butyldimethylsiloxy)-2-(6-methoxycarbonylhexan-2-on-1-yl)cyclopent-2-enone | 159460-48-7

• 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: (R)-4-(tert-Butyldimethylsiloxy)-2-(6-methoxycarbonylhexan-2-on-1-yl)cyclopent-2-enone
• 英文别名: methyl 7-[(3R)-3-[tert-butyl(dimethyl)silyl]oxy-5-oxocyclopenten-1-yl]-6-oxoheptanoate
• CAS: 159460-48-7
• 化学式: C₁₉H₃₂O₅Si
• 分子量: 368.546
• InChiKey: UUBVUIVEWLVFCN-INIZCTEOSA-N

物化性质

• 沸点：
  440.6±45.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-4-(tert-Butyldimethylsiloxy)-2-(6-methoxycarbonylhexan-2-on-1-yl)cyclopent-2-enone 在 吡啶 、 2-thienyl(cyano)copper lithium 、 叔丁基锂 、 氟化氢吡啶 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E,3R,5S)-3-hydroxy-5-methylnon-1-enyl]-5-oxocyclopentyl]-6-oxoheptanoate
  参考文献：
  名称：

  Synthesis of the key component for preparation of 6-ketoprostaglandins by a two-component coupling process: synthesis of 6-keto-prostaglandin E₁, ornoprostil and Δ²-trans-6-ketoprostaglandin E₁

  摘要：

  Starting with commercially available (3S,4R)-3-(methoxymethyloxy)-2-methylidene-4- siloxycyclopentanone-2, useful 6-keto-prostaglandin intermediates 1 have been prepared in good yields by a sequence of reactions which includes treatment with NaBr in the presence of BF3 . OEt(2), Pd-catalysed coupling of the resulting 2-bromomethyl-4-siloxycyclopent-2-enone 3 with the alkenylborane 4 or 9 and conversion of the alkenyl moiety into an epoxy and then into a keto group. The synthesis of 6-keto-PGE(1), ornoprostil and Delta(2)-trans-6-keto-PGE(1) by using 1 is also described.

  DOI：

  10.1039/p19960000715
• 作为产物：
  描述：

  (3S,4R)-4-[tert-butyl(dimethyl)silyl]oxy-3-methoxy-2-methylidenecyclopentan-1-one 在 偶氮二异丁腈 、 tributylstannyllithium 作用下， 反应 3.0h， 生成 (R)-4-(tert-Butyldimethylsiloxy)-2-(6-methoxycarbonylhexan-2-on-1-yl)cyclopent-2-enone
  参考文献：
  名称：

  Radical Addition Reactions to Allylstannanes Having Substituents at C-1. Highly Efficient Synthesis of Enantiomerically Pure .alpha.-Alkylcyclopentenones, the Key Component for Synthesis of Prostaglandins by the Two-Component Coupling Process

  摘要：

  A highly efficient and practical method for the synthesis of enantiomerically pure 4-alkoxy-2-alkyl-2-cyclopenten-1-ones 1, the key component for the preparation of prostaglandins via the two-component coupling process, has been developed. The method involves the preparation of 4-alkoxy-2-methylene-3-(tributylstannyl) cyclopentan-1-one 6 from readily available 4-alkoxy-2-[(diethylamino)methyl]-2-cyclopenten-1-one 5 and its reaction with alkyl radicals.

  DOI：

  10.1021/jo00100a010

文献信息

• Synthesis of the key component for preparation of 6-ketoprostaglandins by a two-component coupling process: synthesis of 6-keto-prostaglandin E₁, ornoprostil and Δ²-trans-6-ketoprostaglandin E₁
  作者：Yasufumi Kawanaka、Naoya Ono、Yukio Yoshida、Sentaro Okamoto、Fumie Sato

  DOI：10.1039/p19960000715

  日期：——

  Starting with commercially available (3S,4R)-3-(methoxymethyloxy)-2-methylidene-4- siloxycyclopentanone-2, useful 6-keto-prostaglandin intermediates 1 have been prepared in good yields by a sequence of reactions which includes treatment with NaBr in the presence of BF3 . OEt(2), Pd-catalysed coupling of the resulting 2-bromomethyl-4-siloxycyclopent-2-enone 3 with the alkenylborane 4 or 9 and conversion of the alkenyl moiety into an epoxy and then into a keto group. The synthesis of 6-keto-PGE(1), ornoprostil and Delta(2)-trans-6-keto-PGE(1) by using 1 is also described.
• Radical Addition Reactions to Allylstannanes Having Substituents at C-1. Highly Efficient Synthesis of Enantiomerically Pure .alpha.-Alkylcyclopentenones, the Key Component for Synthesis of Prostaglandins by the Two-Component Coupling Process
  作者：Yukio Yoshida、Naoya Ono、Fumie Sato

  DOI：10.1021/jo00100a010

  日期：1994.10

  A highly efficient and practical method for the synthesis of enantiomerically pure 4-alkoxy-2-alkyl-2-cyclopenten-1-ones 1, the key component for the preparation of prostaglandins via the two-component coupling process, has been developed. The method involves the preparation of 4-alkoxy-2-methylene-3-(tributylstannyl) cyclopentan-1-one 6 from readily available 4-alkoxy-2-[(diethylamino)methyl]-2-cyclopenten-1-one 5 and its reaction with alkyl radicals.