(2R)-2-cyclohepta-2,4,6-trien-1-ylbutanal | 1254075-89-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R)-2-cyclohepta-2,4,6-trien-1-ylbutanal
• CAS: 1254075-89-2
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: QSTZPHQCHBJKGU-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2R)-2-cyclohepta-2,4,6-trien-1-ylbutanal 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 0.5h， 以13.6 mg的产率得到(R)-2-((2Z,4Z,6Z)-cyclohepta-2,4,6-trienyl)butan-1-ol
  参考文献：
  名称：

  Organocatalytic Asymmetric 1,4-Addition of Aldehydes to Acridiniums Catalyzed by a Diarylprolinol Silyl Ether

  摘要：

  The organocatalytic enantioselective 1,4-addition of aldehydes to acridiniums catalyzed by diarylprolinol silyl ether was achieved to furnish chiral acridanes in both high yields (82-96%) and excellent enantioselectivities (up to 99% ee), which also provides the highly enantioselective intermolecular alpha-alkylation of aldehydes with acridiniums salt.

  DOI：

  10.1021/jo2025114
• 作为产物：
  描述：

  tropylium hexafluorophosphate 、 正丁醛 在 S-α,α-双(3,5-二三氟甲基苯基)脯氨醇三甲基硅醚 、 4-二甲氨基吡啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 (2R)-2-cyclohepta-2,4,6-trien-1-ylbutanal
  参考文献：
  名称：

  Organocatalytic Asymmetric 1,4-Addition of Aldehydes to Acridiniums Catalyzed by a Diarylprolinol Silyl Ether

  摘要：

  The organocatalytic enantioselective 1,4-addition of aldehydes to acridiniums catalyzed by diarylprolinol silyl ether was achieved to furnish chiral acridanes in both high yields (82-96%) and excellent enantioselectivities (up to 99% ee), which also provides the highly enantioselective intermolecular alpha-alkylation of aldehydes with acridiniums salt.

  DOI：

  10.1021/jo2025114

文献信息

• Catalytic stereoselective benzylic C–H functionalizations by oxidative C–H activation and organocatalysis
  作者：Fides Benfatti、Montse Guiteras Capdevila、Luca Zoli、Elena Benedetto、Pier Giorgio Cozzi

  DOI：10.1039/b910185c

  日期：——

  An organocatalytic stereoselective α-alkylation reaction of aldehydes based on C–H activation is presented.

  提出了一种基于C–H活化的有机催化立体选择性α-烷基化反应，用于醛类化合物。
• Organocatalytic Stereoselective α-Alkylation of Aldehydes with Stable Carbocations
  作者：Fides Benfatti、Elena Benedetto、Pier Giorgio Cozzi

  DOI：10.1002/asia.201000160

  日期：2010.9.3

  stereoselective alkylation of aldehydes is carried out with the four stable carbocations 1, 2, 3, 4 in the presence of a catalytic amount (20 mol%) of MacMillan imidazolidinones 5, 6. In all reactions, lutidine was used as a base. The alkylation reactions are investigated at different temperatures with linear and branched aldehydes. In the case of carbocation tropylium fluoroborate, an interesting

  醛的有机催化的立体选择性烷基化是用四个稳定碳阳离子进行1，2，3，4麦克米兰的在催化量的存在（20％摩尔）咪唑啉酮5，6。在所有反应中，二甲基吡啶被用作碱。用直链和支链醛在不同温度下研究烷基化反应。在碳正离子对氟硼酸叔丁基酯的情况下，观察到烷基化产物构型的有趣逆转，这是由反应中的熵效应驱动的。获得通过化学相关性来确定，发现产品的绝对构型为与由麦克米伦提出的模型一般协议来证明在由型催化剂促进了反应得到的立体选择性5，6。
• Organocatalytic Asymmetric 1,4-Addition of Aldehydes to Acridiniums Catalyzed by a Diarylprolinol Silyl Ether
  作者：Tao Liang、Jian Xiao、Zhiyi Xiong、Xingwei Li

  DOI：10.1021/jo2025114

  日期：2012.4.6

  The organocatalytic enantioselective 1,4-addition of aldehydes to acridiniums catalyzed by diarylprolinol silyl ether was achieved to furnish chiral acridanes in both high yields (82-96%) and excellent enantioselectivities (up to 99% ee), which also provides the highly enantioselective intermolecular alpha-alkylation of aldehydes with acridiniums salt.