(R)-2-(cyclohepta-2,4,6-trien-1-yl)-3-phenylpropanal | 1254075-80-3

• 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: (R)-2-(cyclohepta-2,4,6-trien-1-yl)-3-phenylpropanal
• 英文别名: 2-((2Z,4Z,6Z)-cyclohepta-2,4,6-trienyl)-3-phenylpropanal；(2R)-2-cyclohepta-2,4,6-trien-1-yl-3-phenylpropanal
• CAS: 1254075-80-3
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: FNJKTFIKBDDZML-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  (R)-2-(cyclohepta-2,4,6-trien-1-yl)-3-phenylpropanal 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 0.5h， 以16.1 mg的产率得到(R)-2-((2Z,4Z,6Z)-cyclohepta-2,4,6-trienyl)-3-phenylpropan-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：

  苯丙醛 、 tropylium hexafluorophosphate 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 (R)-2-(cyclohepta-2,4,6-trien-1-yl)-3-phenylpropanal
  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

• Electro-Organocatalysis: Enantioselective α-Alkylation of Aldehydes
  作者：Xuan-Huong Ho、Sun-il Mho、Hyuk Kang、Hye-Young Jang

  DOI：10.1002/ejoc.201000453

  日期：——

  The asymmetric organocatalyzed α-alkylation of aldehydes via a cationic radical enamine intermediate was performed under environmentally benign electro-oxidation conditions without the use of chemical oxidants. To promote the desired α-alkylation reaction of aldehydes, various aldehydes with xanthene or cycloheptatriene groups were exposed to electro-organocatalytic conditions to afford optically active

  通过阳离子自由基烯胺中间体对醛进行不对称有机催化的 α-烷基化反应是在环境友好的电氧化条件下进行的，不使用化学氧化剂。为了促进醛的理想 α-烷基化反应，将具有呫吨或环庚三烯基团的各种醛暴露于有机电催化条件下，以良好的收率提供光学活性的 α-取代醛（α-烷基化醛）。基于循环伏安法 (CV) 结果、DFT 计算和控制实验，提出了涉及阳离子自由基烯胺的反应机制。
• 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.