(R)-1-(1-benzyl-2,5-dioxopyrrolidin-3-yl)cyclohexanecarbaldehyde | 1352335-37-5

• 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: (R)-1-(1-benzyl-2,5-dioxopyrrolidin-3-yl)cyclohexanecarbaldehyde
• 英文别名: 1-(1-benzyl-2,5-dioxopyrrolidin-3-yl)cyclohexanecarbaldehyde
• CAS: 1352335-37-5
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: VJQDAPUBPJXCNO-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.45
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  N-苄基马来酰亚胺 、 环己烷基甲醛 在 C₃₀H₄₅N₃O₄ 、 苯甲酸 作用下， 以 甲苯 为溶剂， 以90%的产率得到(R)-1-(1-benzyl-2,5-dioxopyrrolidin-3-yl)cyclohexanecarbaldehyde
  参考文献：
  名称：

  新型伯胺-方酸双酰胺双官能团有机催化剂催化α，α-二取代醛向马来酰亚胺的高度对映选择性迈克尔加成反应

  摘要：

  已开发出新的双官能伯胺-方酸酰胺催化α，α-二取代醛与马来酰亚胺的不对称迈克尔加成反应。这种有机催化不对称反应可轻松获得具有广泛底物范围的官能化琥珀酰亚胺。所需琥珀酰亚胺衍生物的两种对映异构体均以良好至优异的产率（高达98％）和优异的对映选择性（高达> 99％ee）获得。

  DOI：

  10.1016/j.tetlet.2017.10.026

文献信息

• Calixarene-based chiral primary amine thiourea promoted highly enantioselective asymmetric Michael reactions of α,α-disubstituted aldehydes with maleimides
  作者：Mustafa Durmaz、Abdulkadir Sirit

  DOI：10.1016/j.tetasy.2013.09.010

  日期：2013.12

  Calix[4]arene based chiral bifunctional thiourea-primary amines have been shown to act as effective catalysts for the Michael addition of aldehydes to maleimides for the first time. The corresponding adducts were generally obtained preferentially in (R)- or (S)-forms with high yields (up to 99%) and with high to excellent enantioselectivities (up to 98% ee). (C) 2013 Elsevier Ltd. All rights reserved.
• A highly efficient large-scale asymmetric Michael addition of isobutyraldehyde to maleimides promoted by a novel multifunctional thiourea
  作者：Zhi-wei Ma、Yu-xia Liu、Pan-li Li、Hang Ren、Yu Zhu、Jing-chao Tao

  DOI：10.1016/j.tetasy.2011.10.002

  日期：2011.10

  A novel class of chiral multifunctional thioureas bearing a chiral lipophilic beyerane scaffold and a primary amino group were designed and prepared. The thioureas were proven to be effective for catalyzing the asymmetric Michael addition between isobutyraldehyde and maleimides with only 0.5 mol% catalyst loading, and exhibited double asymmetric induction. Both of the catalysts afforded the corresponding adduct with high to excellent yields (up to 98%) and excellent enantioselectivities (up to 99%). Furthermore, this catalytic system can be used efficiently in large-scale reactions with the yields and enantioselectivities being maintained at the same level. (C) 2011 Elsevier Ltd. All rights reserved.