(3R,4R)-4-(1-naphthyl)-3-hydroxy-5-nitro-pentan-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3R,4R)-4-(1-naphthyl)-3-hydroxy-5-nitro-pentan-2-one
• 英文别名: (3R,4R)-4-(1-naphthyl)-3-hydroxy-5-nitropentan-2-one；(3R,4R)-3-hydroxy-4-naphthalen-1-yl-5-nitropentan-2-one
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: VIEGPHGWNKPXGP-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-萘甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙酸铵 、 (2S,2'S)-1-(1-methylethyl)-2,2'-bipyrrolidine 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 173.5h， 生成 (3R,4R)-4-(1-naphthyl)-3-hydroxy-5-nitro-pentan-2-one
  参考文献：
  名称：

  Asymmetric Michael Addition of α-Hydroxyketones to Nitroolefins Catalyzed by Chiral Diamine

  摘要：

  [GRAPHIC]The regio-, stereo-, and enantioselective direct Michael addition of alpha-hydroxyketones to beta-aryinitroolef ins catalyzed by N-/Pr-2,2'-bipyrrolidine is described. The formation of an internal hydrogen bond between the OH group of alpha-hydoxyacetone and the tertiary nitrogen of the catalyst leads to the formation of a rigid cis enamine intermediate that explains the inversion of the expected diastereoselectivity and the very high ee's.

  DOI：

  10.1021/ol0348755

文献信息

• The Use ofN-Alkyl-2,2′-bipyrrolidine Derivatives as Organocatalysts for the Asymmetric Michael Addition of Ketones and Aldehydes to Nitroolefins
  作者：Olivier Andrey、Alexandre Alexakis、Axel Tomassini、Gerald Bernardinelli

  DOI：10.1002/adsc.200404037

  日期：2004.8

  The direct Michael addition of aldehydes and ketones to nitroolefins, catalyzed by N-i-Pr-2,2′-bipyrrolidine, is described. The desired 1,4-adducts are obtained in excellent yields with enantioselectivities up to 95% ee and dr up to 95 : 5 of the syn aldehyde addition product. An unexpected inversion of diastereoselectivity was observed for the addition of α-hydroxy ketones to β-arylnitroolefins with

  描述了由Ni -Pr-2，2'-联吡咯烷催化的醛和酮直接迈克尔加成到硝基烯烃上。以优异的产率获得所需的1,4-加合物，其对映体选择性高达合成醛加成产物的95％ee和dr：95：5 。对于以高达98％ee的对映选择性将α-羟基酮添加到β-芳基硝基烯烃中，观察到了非预期的非对映选择性反转。在α-羟基酮的OH基和催化剂的叔氮之间形成内部氢键导致形成刚性的顺式烯胺中间体，这解释了预期的非对映选择性和非常高的ee。
• Asymmetric Michael Addition of α-Hydroxyketones to Nitroolefins Catalyzed by Chiral Diamine
  作者：Olivier Andrey、Alexandre Alexakis、Gérald Bernardinelli

  DOI：10.1021/ol0348755

  日期：2003.7.1

  [GRAPHIC]The regio-, stereo-, and enantioselective direct Michael addition of alpha-hydroxyketones to beta-aryinitroolef ins catalyzed by N-/Pr-2,2'-bipyrrolidine is described. The formation of an internal hydrogen bond between the OH group of alpha-hydoxyacetone and the tertiary nitrogen of the catalyst leads to the formation of a rigid cis enamine intermediate that explains the inversion of the expected diastereoselectivity and the very high ee's.