(S)-2-[3-(4-甲氧基苯基)-3-氧代-1-苯基丙基]丙二腈 | 1008787-89-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 中文名称: (S)-2-[3-(4-甲氧基苯基)-3-氧代-1-苯基丙基]丙二腈
• 英文名称: (S)-2-(3-(4-methoxyphenyl)-3-oxo-1-phenylpropyl)malononitrile
• 英文别名: 2-[(1S)-3-(4-methoxyphenyl)-3-oxo-1-phenylpropyl]propanedinitrile
• CAS: 1008787-89-0
• 化学式: C₁₉H₁₆N₂O₂
• 分子量: 304.348
• InChiKey: RZIPXNMIGZMCKN-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯甲醛 、 对甲氧基苯乙酮 在 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(1S,2R)-3-[tert-butyl(dimethyl)silyl]oxy-1-(dimethylamino)-1-(4-nitrophenyl)propan-2-yl]thiourea 作用下， 以 甲苯 为溶剂， 反应 192.0h， 生成 (S)-2-[3-(4-甲氧基苯基)-3-氧代-1-苯基丙基]丙二腈
  参考文献：
  名称：

  Chloramphenicol base chemistry. Part 11: 1 chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to α , β -unsaturated ketones

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2017.05.015

文献信息

• Highly Enantioselective Kinetic Resolution of Michael Adducts through N-Heterocyclic Carbene Catalysis: An Efficient Asymmetric Route to Cyclohexenes
  作者：Xiang-Yu Chen、Sun Li、Qiang Liu、Mukesh Kumar、Anssi Peuronen、Kari Rissanen、Dieter Enders

  DOI：10.1002/chem.201802420

  日期：2018.7.11

  A highly efficient strategy for the kinetic resolution of Michael adducts was realized using a chiral N‐heterocyclic carbene catalyst. The kinetic resolution provides a new convenient route to single diastereomers of cyclohexenes and Michael adducts in good yields with high enantiomeric excesses (up to 99 % ee with a selectivity factor of up to 458). This “two flies with one swat” concept allows the

  使用手性N-杂环卡宾催化剂实现了迈克尔加合物动力学拆分的高效策略。动力学拆分提供了一条新的便捷途径，可以以高收率和高对映异构体过量（高达99％ee，选择性因子高达458）获得环己烯和迈克尔加合物的单一非对映异构体。这种“两只苍蝇一拍打”的概念允许通过一次转换同时合成这两种具有合成价值的化合物类别。
• Back to Natural Cinchona Alkaloids: Highly Enantioselective Michael Addition of Malononitrile to Enones
  作者：Alessio Russo、Alessandra Perfetto、Alessandra Lattanzi

  DOI：10.1002/adsc.200900712

  日期：2009.12

  An efficient and convenient highly enantioselective Michael addition of malononitrile to enones has been developed by using quinine as the organocatalyst. The adducts were isolated in excellent yield and high asymmetric induction (up to 95% ee). An easy route to difficultly accessible ester derivatives has been also disclosed.

  通过使用奎宁作为有机催化剂，已经开发了将丙二腈向烯酮高效且方便的高对映选择性迈克尔加成反应。以优异的收率和高的不对称诱导率（高达95％ee）分离了加合物。还公开了一种容易获得的酯衍生物的简便方法。
• Squaramide-catalyzed enantioselective Michael addition of malononitrile to chalcones
  作者：Wen Yang、Yang Jia、Da-Ming Du

  DOI：10.1039/c1ob06302b

  日期：——

  A highly enantioselective Michael addition of malononitrile to chalcones catalyzed by a chiral quinine-derived squaramide catalyst has been developed. This organocatalytic reaction at a very low catalyst loading (0.5 mol%) led to chiral γ-cyano carbonyl compounds in good yields with high enantioselectivities (up to 96% ee) under mild reaction conditions.

  对映体的高对映选择性迈克尔加成 丙二腈已经开发了由手性奎宁衍生的方酰胺催化剂催化的查耳酮。在非常低的催化剂负载量（0.5摩尔％）下，这种有机催化反应在温和的反应条件下以高收率和高对映选择性（最高96％ee）产生了手性的γ-氰基羰基化合物。
• 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。
• 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。