(R)-(+)-2-(4-methoxyphenyl)-4-oxo-4-phenyl-1,1-butanedicarbonitrile | 109012-86-4

• 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: (R)-(+)-2-(4-methoxyphenyl)-4-oxo-4-phenyl-1,1-butanedicarbonitrile
• 英文别名: (R)-3-(4-methoxyphenyl)-2-cyano-5-phenyl-5-oxo-pentano-nitrile；(R)-2-(1-(4-methoxyphenyl)-3-oxo-3-phenylpropyl)malononitrile；2-[(1R)-1-(4-methoxyphenyl)-3-oxo-3-phenylpropyl]propanedinitrile
• CAS: 109012-86-4
• 化学式: C₁₉H₁₆N₂O₂
• 分子量: 304.348
• InChiKey: TYWNNIRHNWPUST-SFHVURJKSA-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

• 作为反应物：
  描述：

  (R)-(+)-2-(4-methoxyphenyl)-4-oxo-4-phenyl-1,1-butanedicarbonitrile 、 臭氧 生成 (S)-N-Nitroso-O-methylprolinol
  参考文献：
  名称：

  ENDERS, DIETER;DEMIR, AYHAN S.;RENDENBACH, BEATRICE E. M., CHEM. BER., 120,(1987) N 10, 1731-1735

  摘要：

  DOI：
• 作为产物：
  描述：

  2-[(1R,3E)-3-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]imino-1-(4-methoxyphenyl)-3-phenylpropyl]propanedinitrile 、 臭氧 以72%的产率得到
  参考文献：
  名称：

  ENDERS, DIETER;DEMIR, AYHAN S.;RENDENBACH, BEATRICE E. M., CHEM. BER., 120,(1987) N 10, 1731-1735

  摘要：

  DOI：

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。
• 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。
• Mesoporous SBA-15 with Short Mesochannels Immobilized Natural Quinine for Asymmetric Michael Addition of Chalcones
  作者：Qiu Chen、Cui Xin、Lan-Lan Lou、Kai Yu、Fei Ding、Shuangxi Liu

  DOI：10.1007/s10562-011-0648-5

  日期：2011.9

  approach for asymmetric organocatalysed Michael addition of malononitrile to chalcones. The catalytic activity was greatly enhanced, compared with the conventional analogue. Furthermore, the enantioselectivity could also be significantly improved for all substrates.Graphical AbstractNatural quinine was firstly immobilized on mesoporous SBA-15 with short mesochannels for the heterogeneous asymmetric Michael

  一种负载在短介孔 SBA-15 上的天然奎宁多相催化剂最初是通过一种简单的共缩合方法合成的，用于不对称有机催化迈克尔加成丙二腈到查耳酮。与传统类似物相比，催化活性大大提高。此外，对所有底物的对映选择性也可以显着提高。图文摘要天然奎宁首先固定在具有短介通道的介孔SBA-15上，用于丙二腈与查耳酮的异质不对称迈克尔加成。与传统类似物相比，催化活性和对映选择性都大大提高。
• 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。
• Organocatalytic Enantioselective Decarboxylative Michael Addition of β-Keto Acids to Dicyanoolefins and Disulfonylolefins
  作者：Yi Wei、Ran Guo、Yanfeng Dang、Jing Nie、Jun-An Ma

  DOI：10.1002/adsc.201600485

  日期：2016.9.1

  A convenient organocatalytic enantioselective decarboxylative Michael addition of β‐keto acids to dicyanoolefins and disulfonylolefins is realized. In the presence of saccharide‐derived chiral amino thioureas, the reaction proceeded smoothly to afford a wide range of the Michael adducts in 62–99% yield with 70–94% ee. Moreover, one of the chiral adducts obtained could be readily converted into the

  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％。