(3S,1’S)-3-[(1’-hydroxy-1’-(2’’-nitrophenyl))methyl]tetrahydropyran-4-one | 1397292-38-4

• 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: (3S,1’S)-3-[(1’-hydroxy-1’-(2’’-nitrophenyl))methyl]tetrahydropyran-4-one
• CAS: 1397292-38-4
• 化学式: C₁₂H₁₃NO₅
• 分子量: 251.239
• InChiKey: BFGJWEUXJHMYKC-BXKDBHETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.23
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  89.67
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  四氢吡喃酮 、 邻硝基苯甲醛 在 lipase from porcine pancreas, type II 作用下， 以 水 、 乙腈 为溶剂， 反应 144.0h， 以62%的产率得到
  参考文献：
  名称：

  Biocatalytic promiscuity: lipase-catalyzed asymmetric aldol reaction of heterocyclic ketones with aldehydes

  摘要：

  The new promiscuous activity of lipase from porcine pancreas, type II (PPL II), has been observed to catalyze the direct asymmetric aldol reaction of heterocyclic ketones with aromatic aldehydes. PPL II showed favorable catalytic activity and had a good adaptability to different substrates in the reaction. The enantioselectivities of up to 87% ee and diastereoselectivities of up to 83:17 (anti/syn) were achieved. It is interesting that PPL II possesses the function of aldolase in organic solvents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.007

文献信息

• Asymmetric Aldol Reaction Catalyzed by Modularly Designed Organocatalysts
  作者：Debarshi Sinha、Tanmay Mandal、Sanjib Gogoi、Joshua J. Goldman、John Cong-gui Zhao

  DOI：10.1002/cjoc.201200639

  日期：2012.9.27

  are amino acids and cinchona alkaloid derivatives, leads to the direct formation of the desired organocatalysts without any synthesis. These modularly designed organocatalysts (MDOs) may be used for catalyzed asymmetric aldol reaction. Depending on structure of the aldehyde substrates, the corresponding aldol products may be obtained in mediocre to excellent ee values (up to 92% ee) with moderate diastereoselectivities

  氨基酸和金鸡纳生物碱衍生物等预催化剂模块的自组装可直接形成所需的有机催化剂，而无需任何合成。这些模块化设计的有机催化剂（MDO）可用于催化不对称的羟醛反应。取决于醛底物的结构，可以以中等的非对映选择性（高达79:21 dr）以中等至优异的ee值（高达92％ee）获得相应的羟醛产物。
• Ficin-catalyzed asymmetric aldol reactions of heterocyclic ketones with aldehydes
  作者：Jian-Ping Fu、Na Gao、Yang Yang、Zhi Guan、Yan-Hong He

  DOI：10.1016/j.molcatb.2013.06.016

  日期：2013.12

  Ficin from fig tree latex displayed a promiscuous activity to catalyze the direct asymmetric aldol reactions of heterocyclic ketones with aromatic aldehydes. Ficin showed good substrate adaptability to different heterocyclic ketones containing nitrogen, oxygen or sulfur. The enantioselectivities up to 81% ee and diastereoselectivities up to 86:14 (anti/syn) were achieved under the optimized reaction conditions. (C) 2013 Elsevier B.V. All rights reserved.