ethyl 5-(4-chlorophenyl)-5-hydroxy-2,4-dimethyl-2,3-pentadienoate

• 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: ethyl 5-(4-chlorophenyl)-5-hydroxy-2,4-dimethyl-2,3-pentadienoate
• 英文别名: ethyl 5-(4-chlorophenyl)-5-hydroxy-2,4-dimethylpenta-2,3-dienoate
• 化学式: C₁₅H₁₇ClO₃
• 分子量: 280.751
• InChiKey: SOVVHDPIAOSLPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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 5-(4-chlorophenyl)-5-hydroxy-2,4-dimethyl-2,3-pentadienoate 在 三丁基膦 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以67%的产率得到6-(4-chlorophenyl)-3,5-dimethyl-2H-pyran-2-one
  参考文献：
  名称：

  Guanidine-Catalyzed γ-Selective Morita–Baylis–Hillman Reactions on α,γ-Dialkyl-Allenoates: Access to Densely Substituted Heterocycles

  摘要：

  N-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) was discovered as an excellent catalyst for the Morita-Baylis-Hillman reaction for previously hard-to-activate ,-dialkyl allenoate substrates. The obtained densely substituted allenic alcohols, which are generally inaccessible with other Lewis base catalysts, could be further converted into 2,5-dihydrofuran and 2H-pyran-2-one heterocyclic structures with challenging substitution patterns.

  DOI：

  10.1055/s-0033-1339471
• 作为产物：
  描述：

  ethyl 2-methylpenta-2,3-dienoate 在 C₆₄H₂₉F₂₄NO₄S₂ 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 120.75h， 生成 ethyl 5-(4-chlorophenyl)-5-hydroxy-2,4-dimethyl-2,3-pentadienoate
  参考文献：
  名称：

  手性异戊烯经烷基山形醛醇缩醛反应

  摘要：

  在本文中，我们描述了催化对映选择性炔烃Mukaiyama醛醇缩合反应的发展。该反应由新设计的手性二磺酰亚胺催化，并以高收率和极佳的区域，非对映和对映选择性提供手性烯丙酸酯。与多种炔基取代的乙烯酮缩醛组合使用，我们的方法可耐受多种醛类。反应产物可以容易地衍生以提供各种高度取代的对映体富集的结构单元。

  DOI：

  10.1002/anie.201603649

文献信息

• Diastereomerically Pure Morita–Baylis–Hillman (MBH) Acetates and Carbonates from Allenic α- and γ-MBH Alcohols
  作者：Philipp Selig、Tai-Lam Nghiem

  DOI：10.1055/s-0034-1380140

  日期：——

  Diastereomerically pure allenic Morita-Baylis-Hillman (MBH) acetates and carbonates have been prepared from their corresponding - and -MBH alcohols. Derivatizations proceeded under standard conditions without epimerization. Both - and -MBH derivatives were shown to be suitable substrates for further transformations.
• Chiral Allenes via Alkynylogous Mukaiyama Aldol Reaction
  作者：Aurélien Tap、Aurélie Blond、Vijay N. Wakchaure、Benjamin List

  DOI：10.1002/anie.201603649

  日期：2016.7.25

  development of a catalytic enantioselective alkynylogous Mukaiyama aldol reaction. The reaction is catalyzed by a newly designed chiral disulfonimide and delivers chiral allenoates in high yields and with excellent regio‐, diastereo‐, and enantioselectivity. Our process tolerates a broad range of aldehydes in combination with diverse alkynyl‐substituted ketene acetals. The reaction products can be readily

  在本文中，我们描述了催化对映选择性炔烃Mukaiyama醛醇缩合反应的发展。该反应由新设计的手性二磺酰亚胺催化，并以高收率和极佳的区域，非对映和对映选择性提供手性烯丙酸酯。与多种炔基取代的乙烯酮缩醛组合使用，我们的方法可耐受多种醛类。反应产物可以容易地衍生以提供各种高度取代的对映体富集的结构单元。
• Guanidine-Catalyzed γ-Selective Morita–Baylis–Hillman Reactions on α,γ-Dialkyl-Allenoates: Access to Densely Substituted Heterocycles
  作者：Philipp Selig、Aleksej Turočkin、William Raven

  DOI：10.1055/s-0033-1339471

  日期：——

  N-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) was discovered as an excellent catalyst for the Morita-Baylis-Hillman reaction for previously hard-to-activate ,-dialkyl allenoate substrates. The obtained densely substituted allenic alcohols, which are generally inaccessible with other Lewis base catalysts, could be further converted into 2,5-dihydrofuran and 2H-pyran-2-one heterocyclic structures with challenging substitution patterns.