2,6-Bis(1,1-dimethylethyl)-4-methylphenyl propenoate | 30392-11-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2,6-Bis(1,1-dimethylethyl)-4-methylphenyl propenoate
• 英文别名: 2,6-di-tert-butyl-4-methylphenyl acrylate；2-Propenoic acid, 2,6-bis(1,1-dimethylethyl)-4-methylphenyl ester；(2,6-ditert-butyl-4-methylphenyl) prop-2-enoate
• CAS: 30392-11-1
• 化学式: C₁₈H₂₆O₂
• 分子量: 274.403
• InChiKey: QGMNRSRPONKEIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-Bis(1,1-dimethylethyl)-4-methylphenyl propenoate 、 diisopinocampheylborane 以 乙醚 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  (Diisopinocampheyl)borane-Mediated Reductive Aldol Reactions of Acrylate Esters: Enantioselective Synthesis of Anti-Aldols

  摘要：

  The (diisopinocampheyl)borane promoted reductive aldol reaction of acrylate esters 4 is described. Isomerization of the kinetically formed Z(O)-enolborinate 5Z to the thermodynamic E(O)-enolborinate 5E via 1,3-boratropic shifts, followed by treatment with representative achiral aldehydes, leads to anti-alpha-methyl-beta-hydroxy esters 9 or 10 with excellent diastereo- (up to >= 20:1 dr) and enantioselectivity (up to 87% ee). The results of double asymmetric reactions of 5E with several chiral aldehydes are also presented.

  DOI：

  10.1021/ol401679g
• 作为产物：
  描述：

  2,6-di-tert-butyl-4-methylphenyl diazoacetoacetate 在 tetrakis(trifluoroacetato)rhodium(II) 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 2,6-Bis(1,1-dimethylethyl)-4-methylphenyl propenoate
  参考文献：
  名称：

  Synthesis and Chemistry of Donor/Acceptor-Substituted Cyclopropenes

  摘要：

  Rhodium(II) acetate, or trifluoroacetate-catalyzed decomposition of 1-diazo-2-(trialkylsiloxy)propenes with electron-withdrawing groups at the 1-position results in the formation of highly reactive cyclopropenes. These cyclopropenes contain both donor and acceptor substituents on the alkene and are very susceptible to ring opening and fragmentation reactions, Nevertheless, when appropriately functionalized with bulky substituents they can be of sufficient stability to be isolated and characterized.

  DOI：

  10.1021/jo00128a027

文献信息

• DE1922815
  申请人：——

  公开号：——

  公开（公告）日：——
• (Diisopinocampheyl)borane-Mediated Reductive Aldol Reactions of Acrylate Esters: Enantioselective Synthesis of <i>Anti</i>-Aldols
  作者：Christophe Allais、Philippe Nuhant、William R. Roush

  DOI：10.1021/ol401679g

  日期：2013.8.2

  The (diisopinocampheyl)borane promoted reductive aldol reaction of acrylate esters 4 is described. Isomerization of the kinetically formed Z(O)-enolborinate 5Z to the thermodynamic E(O)-enolborinate 5E via 1,3-boratropic shifts, followed by treatment with representative achiral aldehydes, leads to anti-alpha-methyl-beta-hydroxy esters 9 or 10 with excellent diastereo- (up to >= 20:1 dr) and enantioselectivity (up to 87% ee). The results of double asymmetric reactions of 5E with several chiral aldehydes are also presented.
• Synthesis and Chemistry of Donor/Acceptor-Substituted Cyclopropenes
  作者：Huw M. L. Davies、Jeffrey H. Houser、Craig Thornley

  DOI：10.1021/jo00128a027

  日期：1995.11

  Rhodium(II) acetate, or trifluoroacetate-catalyzed decomposition of 1-diazo-2-(trialkylsiloxy)propenes with electron-withdrawing groups at the 1-position results in the formation of highly reactive cyclopropenes. These cyclopropenes contain both donor and acceptor substituents on the alkene and are very susceptible to ring opening and fragmentation reactions, Nevertheless, when appropriately functionalized with bulky substituents they can be of sufficient stability to be isolated and characterized.