(R)-2-(10-methyl-9,10-dihydroacridin-9-yl)hexanal | 1333149-80-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (R)-2-(10-methyl-9,10-dihydroacridin-9-yl)hexanal
• 英文别名: (2R)-2-(10-methyl-9H-acridin-9-yl)hexanal
• CAS: 1333149-80-6
• 化学式: C₂₀H₂₃NO
• 分子量: 293.409
• InChiKey: VVLJKZODXGLFQZ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-(10-methyl-9,10-dihydroacridin-9-yl)hexanal 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 0.5h， 以26.9 mg的产率得到(R)-2-(10-methyl-9,10-dihydroacridin-9-yl)hexan-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：

  N-甲基吖啶鎓碘化物 、 正己醛 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 (R)-2-(10-methyl-9,10-dihydroacridin-9-yl)hexanal
  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

• Organocatalytic Asymmetric Intermolecular Dehydrogenative α-Alkylation of Aldehydes Using Molecular Oxygen as Oxidant
  作者：Bo Zhang、Shi-Kai Xiang、Li−He Zhang、Yuxin Cui、Ning Jiao

  DOI：10.1021/ol202090a

  日期：2011.10.7

  An organocatalytic enantioselective intermolecular oxidative dehydrogenative α-alkylation of aldehydes via benzylic C–H bond activation has been developed. The asymmetric reaction is smoothly fulfilled by using simple and green molecular oxygen as the oxidant. Two hydrogen dissociations make this transformation more environmentally benign because of high atom efficiency.

  通过苄基CH键的活化，开发了醛的有机催化对映选择性分子间氧化脱氢α-烷基。通过使用简单的绿色分子氧作为氧化剂，可以平稳地完成不对称反应。由于高的原子效率，两个氢离解使这种转变在环境上更加无害。
• 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.