(S)-2-(1-(4-fluorophenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanal | 1352335-17-1

• 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: (S)-2-(1-(4-fluorophenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanal
• 英文别名: 2-[(3S)-1-(4-fluorophenyl)-2,5-dioxopyrrolidin-3-yl]-2-methylpropanal
• CAS: 1352335-17-1
• 化学式: C₁₄H₁₄FNO₃
• 分子量: 263.268
• InChiKey: SYZKMMUVCLLICZ-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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：
  4

反应信息

• 作为产物：
  描述：

  1-(4-氟苯基)-吡咯-2,5-二酮 、 异丁醛 在 C₂₆H₄₃N₃OS 作用下， 以 甲苯 为溶剂， 以95%的产率得到(S)-2-(1-(4-fluorophenyl)-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

• N-Primary-amine tetrapeptide-catalyzed highly asymmetric Michael addition of aliphatic aldehydes to maleimides
  作者：Zhi-Hong Du、Wen-Juan Qin、Bao-Xiu Tao、Meng Yuan、Chao-Shan Da

  DOI：10.1039/d0ob01457e

  日期：——

  highly asymmetric Michael addition reaction between maleimides and aliphatic aldehydes catalyzed by low-loading β-turn tetrapeptides with excellent yields and enantioselectivities at room temperature was reported. α-Branched and α-unbranched aldehydes both are suitable nucleophiles. N-Aryl, alkyl and hydrogen maleimides all are well tolerated and led to high yields and enantioselectivities. The transformation

  报道了由低负载β-转角四肽催化的马来酰亚胺和脂肪醛之间的高度不对称迈克尔加成反应，在室温下具有优异的收率和对映选择性。α-支链和 α-非支链醛都是合适的亲核试剂。N-芳基、烷基和氢马来酰亚胺均具有良好的耐受性并导致高产率和对映选择性。转化可以扩大到克级而不降低产率和对映选择性。此外，将琥珀酰亚胺转化为γ-内酰胺和γ-内酯，显示了这项工作的良好实用性。所提出的反应机制中的一些反应中间体可以用 HR-MS 方法捕获。
• 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。
• Enantioselective Michael addition of aldehydes to maleimides catalysed by surface-adsorbed natural amino acids
  作者：Viktória Kozma、György Szőllősi

  DOI：10.1039/d2cy00545j

  日期：——

  inorganic–organic hybrid catalysts using amino acids such as L-phenylalanine and clay minerals or alumina, which were highly active and provided excellent enantioselectivities, up to 99%, in the addition of aldehydes to a large variety of N-substituted maleimides. Examinations indicated the occurrence of the asymmetric reaction on the surface of the recyclable solid hybrid materials. The catalytic materials

  羰基化合物与N-取代马来酰亚胺的不对称迈克尔加成是获得光学纯琥珀酰亚胺的重要方法，琥珀酰亚胺是重要的手性精细化工中间体。环保和可持续的程序需要使用从天然手性来源和廉价助剂获得的多相、可回收催化剂。在这里，我们报告了使用氨基酸（如L-苯丙氨酸和粘土矿物或氧化铝）原位形成的手性无机-有机杂化催化剂的应用，这些催化剂在将醛添加到种类繁多的N-取代的马来酰亚胺。检查表明可回收的固体杂化材料表面发生了不对称反应。通过热重分析、XRD、FT-IR和拉曼光谱、SEM和吸附实验对催化材料进行了检测。这些方法的结果表明，氨基酸以表面微晶的形式沉积或嵌入层状阳离子交换剂中，两者都作为手性源的供应，而反应由吸附在表面上的手性化合物催化。该催化体系用于方便地制备克级手性琥珀酰亚胺，易于通过结晶纯化。因此，这些手性杂化材料是方便的非均相催化剂，用于使用天然手性源获得高光学纯度的有价值的化合物，
• 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.