2-(1-(3-bromophenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanal | 1352335-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-(1-(3-bromophenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanal
• 英文别名: (S)-2-(1-(3-bromophenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanal；2-[(3S)-1-(3-bromophenyl)-2,5-dioxopyrrolidin-3-yl]-2-methylpropanal
• CAS: 1352335-19-3
• 化学式: C₁₄H₁₄BrNO₃
• 分子量: 324.174
• InChiKey: GCHOBDUHPRVAHC-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(3-溴苯基)-1H-吡咯-2,5-二酮 、 异丁醛 在 C₂₆H₄₃N₃OS 作用下， 以 甲苯 为溶剂， 以72%的产率得到2-(1-(3-bromophenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanal
  参考文献：
  名称：

  新型双萜衍生的双功能硫脲催化剂促进的高对映选择性迈克尔加成反应：手性琥珀酰亚胺衍生物的双立体控制方法

  摘要：

  描述了双立体控制的有机催化不对称迈克尔加成取代琥珀酰亚胺的合成。从醛和马来酰亚胺开始，将两种特殊的手性双萜衍生的双官能硫脲分别用作丁二酰亚胺时，琥珀酰亚胺的两种对映异构体均可以高至优异的收率（高达98％）和对映选择性（高达99％）获得。催化剂。而且，这些催化剂可以有效地用于大规模催化合成，且产率和对映选择性相同。手性00：000–000，2014年。©2014 Wiley Periodicals，Inc.

  DOI：

  10.1002/chir.22279

文献信息

• Highly enantioselective Michael addition of α,α-disubstituted aldehydes to maleimides catalyzed by new primary amine-squaramide bifunctional organocatalysts
  作者：Zhi-wei Ma、Xiao-feng Liu、Jun-tao Liu、Zhi-jing Liu、Jing-chao Tao

  DOI：10.1016/j.tetlet.2017.10.026

  日期：2017.11

  amine-squaramides catalyzed asymmetric Michael addition reaction of α,α-disubstituted aldehydes to maleimides has been developed. This organocatalytic asymmetric reaction provides easy access to functionalized succinimides with a broad substrate scope. Both enantiomers of desired succinimide derivatives were obtained in good to excellent yields (up to 98%) with excellent enantioselectivities (up to >99% ee)

  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。
• 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.
• Highly EnantioselectiveMichael Addition Promoted by a New Diterpene-Derived Bifunctional Thiourea Catalyst: A Doubly Stereocontrolled Approach to Chiral Succinimide Derivatives
  作者：Zhong-Tai Song、Tao Zhang、Hai-Long Du、Zhi-Wei Ma、Chang-Hua Zhang、Jing-Chao Tao

  DOI：10.1002/chir.22279

  日期：2014.2

  A doubly stereocontrolled organocatalytic asymmetric Michael addition to the synthesis of substituted succinimides is described. Starting from aldehydes and maleimides, both enantiomers of the succinimides could be obtained in high to excellent yields (up to 98%) and enantioselectivities (up to 99%) when one of the two special chiral diterpene‐derived bifunctional thioureas was individually used as

  描述了双立体控制的有机催化不对称迈克尔加成取代琥珀酰亚胺的合成。从醛和马来酰亚胺开始，将两种特殊的手性双萜衍生的双官能硫脲分别用作丁二酰亚胺时，琥珀酰亚胺的两种对映异构体均可以高至优异的收率（高达98％）和对映选择性（高达99％）获得。催化剂。而且，这些催化剂可以有效地用于大规模催化合成，且产率和对映选择性相同。手性00：000–000，2014年。©2014 Wiley Periodicals，Inc.