(R)-4-(tert-Butyldimethylsiloxy)-2-<(E)-6-methoxycarbonyl-2-oxohex-5-enyl>cyclopent-2-enone | 176446-44-9

• 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-<(E)-6-methoxycarbonyl-2-oxohex-5-enyl>cyclopent-2-enone
• 英文别名: methyl (E)-7-[(3R)-3-[tert-butyl(dimethyl)silyl]oxy-5-oxocyclopenten-1-yl]-6-oxohept-2-enoate
• CAS: 176446-44-9
• 化学式: C₁₉H₃₀O₅Si
• 分子量: 366.53
• InChiKey: LZJLUJICVBMJDU-DZZUKKPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 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-<(E)-6-methoxycarbonyl-2-oxohex-5-enyl>cyclopent-2-enone 在 吡啶 、 phosphate buffer 、 2-thienyl(cyano)copper lithium 、 叔丁基锂 、 氟化氢吡啶 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 12.0h， 生成 Δ²-trans-6-Keto-prostaglandin E1
  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：

  (R)-2-Bromomethyl-4-(tert-butyldimethylsiloxy)cyclopent-2-enone 在 四(三苯基膦)钯 甲醇 、 sodium hydroxide 、 三氟化硼乙醚 、 bis(cyclohexanyl)borane 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 9.5h， 生成 (R)-4-(tert-Butyldimethylsiloxy)-2-<(E)-6-methoxycarbonyl-2-oxohex-5-enyl>cyclopent-2-enone
  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

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.