(+)-2-(1-(4-chlorophenyl)-3-oxo-3-phenylpropyl)malononitrile

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (+)-2-(1-(4-chlorophenyl)-3-oxo-3-phenylpropyl)malononitrile
• 英文别名: 2-[(1R)-1-(4-chlorophenyl)-3-oxo-3-phenylpropyl]propanedinitrile
• 化学式: C₁₈H₁₃ClN₂O
• 分子量: 308.767
• InChiKey: KGKZZAYYUXMQJC-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氯苄亚基丙二腈 、 苯甲酰乙酸 在 Thiourea, N-[(1S,2S)-2-(1-piperidinyl)cyclohexyl]-N'-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)- 作用下， 以 甲苯 为溶剂， 反应 144.0h， 以86%的产率得到
  参考文献：
  名称：

  β-酮酸对二氰基烯烃和二磺酰基烯烃的有机催化对映选择性脱羧迈克尔加成

  摘要：

  实现了将β-酮酸方便地有机催化对映选择性脱羧迈克尔加成到二氰基烯烃和二磺酰基烯烃中。在糖衍生的手性氨基硫脲的存在下，反应顺利进行，以62-99％的收率和70-94％ee的收率提供了多种迈克尔加合物。此外，所获得的手性加合物之一可以容易地在四个步骤中以85％ee转化为单氟化产物，总产率为68％。

  DOI：

  10.1002/adsc.201600485

文献信息

• Enantioselective Michael addition of malononitrile to chalcones catalyzed by a simple quinine–Al(OiPr)3 complex: a simple method for the synthesis of a chiral 4H-pyran derivative
  作者：Jian Shi、Min Wang、Ling He、Ke Zheng、Xiaohua Liu、Lili Lin、Xiaoming Feng

  DOI：10.1039/b908632c

  日期：——

  Enantioselective Michael addition of malononitrile to chalcones was catalyzed by a simple quinine and Al(O(i)Pr)(3) complex and products were obtained in good ee as well as high yields, which facilitated the asymmetric synthesis of a biologically active 4H-pyran compound.

  通过简单的奎宁和Al（O（i）Pr）（3）配合物催化丙二醛向对苯二酚的对映选择性迈克尔加成反应，并获得了良好的ee和高收率的产物，这促进了具有生物活性的4H-的不对称合成吡喃化合物。
• Enantioselective Conjugate Addition of Malononitrile to Chalcones Promoted by α,α-L-Diaryl Prolinols: Noncovalent versus Covalent Catalysis?
  作者：Alessio Russo、Amedeo Capobianco、Alessandra Perfetto、Alessandra Lattanzi、Andrea Peluso

  DOI：10.1002/ejoc.201001466

  日期：2011.4

  conjugate addition of malononitrile to trans-chalcones has been investigated as a case study using easily available α,α-L-diaryl prolinols as promoters. Both experimental and computational results are consistent with a bifunctional noncovalent mode of activation of the reactive partners, provided by the secondary amine and hydroxyl groups of the promoter as general base and acid catalysis. This most

  丙二腈与反式查耳酮的对映选择性共轭加成已作为案例研究，使用容易获得的 α,α-L-二芳基脯氨醇作为促进剂。实验和计算结果都与反应伙伴的双功能非共价活化模式一致，由作为一般碱和酸催化的促进剂的仲胺和羟基提供。这种最能负担得起的途径预测了 R 型加合物的主要形成，这与实验结果一致。本研究首次解决了脯氨酸衍生物通过非共价催化辅助产物形成的能力，类似于金鸡纳生物碱的典型作用模式。
• Quinine catalysed asymmetric Michael additions in a sustainable solvent
  作者：José A. Castro-Osma、James W. Comerford、Samantha Heath、Oliver Jones、Maria Morcillo、Michael North

  DOI：10.1039/c4ra12132e

  日期：——

  Diethyl carbonate is shown to be a suitable, sustainable solvent in which to carry out quinine catalysed asymmetric Michael additions of malononitriles to enones.

  乙基碳酸酯被证明是一种适合的可持续溶剂，可用于进行奎宁催化的马来酸二腈对烯酮的不对称迈克尔加成反应。
• Thieme Chemistry Journals Awardees – Where Are They Now? A Stereoselective Tripeptide Catalyst for Conjugate Addition Reactions of Acetophenones to Dicyanoolefins
  作者：Helma Wennemers、Tobias Schnitzer

  DOI：10.1055/s-0036-1588964

  日期：2017.7

  Peptides of the type H-Pro-Pro-Xaa-NH2 were evaluated as catalysts for conjugate addition reactions of acetophenones to cyanoolefins. Tripeptide H- d -Pro-Pro-Glu-NH2 with a carboxylic acid moiety in the side chain of Xaa was identified as a catalyst that provides γ,γ-dicyanoacetophenones in yields of up to 90% and stereoselectivies of up to 88:12 er.

  H-Pro-Pro-Xaa-NH2 类型的肽被评估为苯乙酮与氰烯烃共轭加成反应的催化剂。在 Xaa 的侧链中具有羧酸部分的三肽 H- d -Pro-Pro-Glu-NH2 被鉴定为一种催化剂，可提供高达 90% 的产率和高达 88:12 的立体选择性的 γ,γ-二氰基苯乙酮呃。
• Chloramphenicol base chemistry. Part 11: 1 chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to α , β -unsaturated ketones
  作者：Linjie Yan、Haifeng Wang、Fangjun Xiong、Yuan Tao、Yan Wu、Fener Chen

  DOI：10.1016/j.tetasy.2017.05.015

  日期：2017.7

  The first chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to alpha,beta-unsaturated ketones is reported. The Michael adducts were obtained in good to excellent yields (up to 98% yield) and enantioselectivities (up to 94% ee). This reaction has a broad substrate scope to various alpha,beta-unsaturated ketones. With this in mind, this methodology was successfully applied to the synthesis of a chiral piperidone, an advanced building block for dihydropyridinone P2X(7) receptor antagonists. (C) 2017 Published by Elsevier Ltd.