Ethyl 3-hydroxy-2-prop-2-enylpent-4-enoate | 204526-78-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: Ethyl 3-hydroxy-2-prop-2-enylpent-4-enoate
• CAS: 204526-78-3
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: VEQJTRFGEKQFRP-UHFFFAOYSA-N

物化性质

• 沸点：
  264.053±35.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  0.993±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 3-hydroxy-2-prop-2-enylpent-4-enoate 在 咪唑 、 二异丁基氢化铝 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 3-[Tert-butyl(dimethyl)silyl]oxy-2-prop-2-enylpent-4-en-1-ol
  参考文献：
  名称：

  Stereoselective Synthesis of Carbobicyclics via Organoyttrium-Catalyzed Sequential Cyclization/Silylation Reactions

  摘要：

  The sequential cyclization/silylation of 1,5-dienes and 1,6-dienes was effected under mild reaction conditions using catalytic quantities of Cp-2*YMe . THF. The process provides carbobicyclics in high yields and with excellent selectivities. The active catalyst is postulated to be Cp-2*YH . THF, which is generated in situ. A variety of alkenyl-substituted cyclopentane and cyclohexane substrates were examined. The high diastereoselectivities apparently originate fi om a preference for a chairlike transition structure that minimizes unfavorable steric interactions between the bulky Cp* ligands of the catalyst and the preexisting ring of the substrate. Acyclic triene precursors, 4-ethenyl-substituted 1,5-heptadienes and 5-ethenyl-substituted 1,8-nonadienes were also examined. These triene substrates, when exposed to the cyclization/silylation protocol, provide the strained trans-bicyclo[3.3.0]octanes and trans-decalin systems in high yield with excellent diastereoselectivity. The high selectivity is again attributed to the preference for a chairlike transition structure. The cyclized organosilane products isolated from these reactions were easily converted to the more versatile alcohols utilizing known oxidation methods.

  DOI：

  10.1021/jo9721352
• 作为产物：
  描述：

  4-戊烯酸乙酯 、 丙烯醛 在 lithium diisopropyl amide 作用下， 以90%的产率得到Ethyl 3-hydroxy-2-prop-2-enylpent-4-enoate
  参考文献：
  名称：

  Stereoselective Synthesis of Carbobicyclics via Organoyttrium-Catalyzed Sequential Cyclization/Silylation Reactions

  摘要：

  The sequential cyclization/silylation of 1,5-dienes and 1,6-dienes was effected under mild reaction conditions using catalytic quantities of Cp-2*YMe . THF. The process provides carbobicyclics in high yields and with excellent selectivities. The active catalyst is postulated to be Cp-2*YH . THF, which is generated in situ. A variety of alkenyl-substituted cyclopentane and cyclohexane substrates were examined. The high diastereoselectivities apparently originate fi om a preference for a chairlike transition structure that minimizes unfavorable steric interactions between the bulky Cp* ligands of the catalyst and the preexisting ring of the substrate. Acyclic triene precursors, 4-ethenyl-substituted 1,5-heptadienes and 5-ethenyl-substituted 1,8-nonadienes were also examined. These triene substrates, when exposed to the cyclization/silylation protocol, provide the strained trans-bicyclo[3.3.0]octanes and trans-decalin systems in high yield with excellent diastereoselectivity. The high selectivity is again attributed to the preference for a chairlike transition structure. The cyclized organosilane products isolated from these reactions were easily converted to the more versatile alcohols utilizing known oxidation methods.

  DOI：

  10.1021/jo9721352

文献信息

• Stereoselective Synthesis of Carbobicyclics via Organoyttrium-Catalyzed Sequential Cyclization/Silylation Reactions
  作者：Gary A. Molander、Paul J. Nichols、Bruce C. Noll

  DOI：10.1021/jo9721352

  日期：1998.4.1

  The sequential cyclization/silylation of 1,5-dienes and 1,6-dienes was effected under mild reaction conditions using catalytic quantities of Cp-2*YMe . THF. The process provides carbobicyclics in high yields and with excellent selectivities. The active catalyst is postulated to be Cp-2*YH . THF, which is generated in situ. A variety of alkenyl-substituted cyclopentane and cyclohexane substrates were examined. The high diastereoselectivities apparently originate fi om a preference for a chairlike transition structure that minimizes unfavorable steric interactions between the bulky Cp* ligands of the catalyst and the preexisting ring of the substrate. Acyclic triene precursors, 4-ethenyl-substituted 1,5-heptadienes and 5-ethenyl-substituted 1,8-nonadienes were also examined. These triene substrates, when exposed to the cyclization/silylation protocol, provide the strained trans-bicyclo[3.3.0]octanes and trans-decalin systems in high yield with excellent diastereoselectivity. The high selectivity is again attributed to the preference for a chairlike transition structure. The cyclized organosilane products isolated from these reactions were easily converted to the more versatile alcohols utilizing known oxidation methods.