(R)-ethyl 1-benzyl-2-methyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3-carboxylate | 1248337-48-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (R)-ethyl 1-benzyl-2-methyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3-carboxylate
• 英文别名: ethyl (S)-1-benzyl-2-methyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3-carboxylate；ethyl (4R)-1-benzyl-2-methyl-4-(4-nitrophenyl)-4H-pyridine-3-carboxylate
• CAS: 1248337-48-5
• 化学式: C₂₂H₂₂N₂O₄
• 分子量: 378.428
• InChiKey: MGURMORCIKGGLH-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 在 S-α,α-双(3,5-二三氟甲基苯基)脯氨醇三甲基硅醚 、 苯甲酸 作用下， 以 水 、 甲苯 为溶剂， 反应 4.08h， 生成 (R)-ethyl 1-benzyl-2-methyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3-carboxylate 、 ethyl 1-benzyl-2-methyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  对映选择性有机催化氮杂-烯型多米诺反应导致1,4-二氢吡啶

  摘要：

  开发了一种新的通用方法，可通过（S）-二芳基脯氨醇-TMS醚V和苯甲酸（BA）共同催化的有机催化不对称氮杂-烯型级联反应获得高度对映体富集的1,4-二氢吡啶（DHPs）3。脂族和芳基烯醛1均与烯胺酮和β-烯胺酯2平稳反应，从而以高对映选择性和良好收率提供高度官能化的1,4-DHP 3。

  DOI：

  10.1021/jo200095e

文献信息

• Brønsted Acid-Thiourea Co-catalysis: Asymmetric Synthesis of Function­alized 1,4-Dihydropyridines from β-Enamino Esters and α,β-Unsaturated ­Aldehydes
  作者：Yoshiji Takemoto、Kohzo Yoshida、Tsubasa Inokuma、Kiyosei Takasu

  DOI：10.1055/s-0030-1258090

  日期：2010.7

  A Bronsted acid and a novel thiourea derivative co-catalyze the addition of β-enamino esters to a,β-unsaturated aldehydes leading to functionalized 1,4-dihydropyridines with moderate to good enantioselectivity. A regioselective synthesis of 1,2-dihydropyridines from a,β-unsaturated aldehydes is also described.

  布朗斯台德酸和新型硫脲衍生物共催化 β-烯氨基酯与 α,β-不饱和醛的加成，从而产生具有中等至良好对映选择性的官能化 1,4-二氢吡啶。还描述了从 a,β-不饱和醛区域选择性合成 1,2-二氢吡啶。
• Fully Diastereoselective Synthesis of Polysubstituted, Functionalized Piperidines and Decahydroquinolines Based on Multicomponent Reactions Catalyzed by Cerium(IV) Ammonium Nitrate
  作者：Padmakar A. Suryavanshi、Vellaisamy Sridharan、Swarupananda Maiti、J. Carlos Menéndez

  DOI：10.1002/chem.201402607

  日期：2014.7.7

  The cerium(IV) ammonium nitrate (CAN)‐catalyzed, three‐component reaction between primary amines, β‐dicarbonyl compounds, and α,β‐unsaturated aldehydes in ethanol heated to reflux, constitutes a general, one‐pot synthesis of 1,4‐dihydropyridines. Their reduction with sodium triacetoxyborohydride furnished piperidine derivatives bearing up to five substituents with full diastereoselectivity in a hitherto

  硝酸铈（IV）硝酸铵（CAN）催化的伯胺，β-二羰基化合物和乙醇中加热到回流的α，β-不饱和醛之间的三组分反应构成了一般的一锅法合成，即1， 4-二氢吡啶 用三乙酰氧基硼氢化钠将它们还原，得到具有多达五个取代基的哌啶衍生物，并且以迄今难以达到的立体化学排列具有完全非对映选择性。在与通常对还原敏感的几个官能团相容的温和还原条件下，反应进行时对映体纯度没有明显损失。八氢喹啉-5-酮衍生物是通过初始多组分反应的改良形式制备的，不适用于三乙酰氧基硼氢化钠介导的还原反应，
• Catalytic Asymmetric Synthesis of Both Enantiomers of 4‑Substituted 1,4-Dihydropyridines with the Use of Bifunctional Thiourea-Ammonium Salts Bearing Different Counterions
  作者：Kohzo Yoshida、Tsubasa Inokuma、Kiyosei Takasu、Yoshiji Takemoto

  DOI：10.3390/molecules15118305

  日期：——

  Organoammonium salts composed of a Brønsted acid and an anilinothiourea promoted the Michael addition of β-keto esters and α,β-unsaturated aldehydes in the presence of primary amines to give functionalized 1,4-dihydropyridines enantioselectively. With the use of the different Brønsted acids such as DFA and HBF4 with the same bifunctional thiourea, both enantiomers of 4-substituted 1,4-dihydropyridine were synthesized from the same starting materials.

  由布朗斯台德酸和苯胺基硫脲组成的有机铵盐促进 β-酮酯和 α,β-不饱和醛在伯胺存在下发生迈克尔加成，从而对映选择性地生成官能化的 1,4-二氢吡啶。使用不同的布朗斯台德酸（例如 DFA 和 HBF4）与相同的双官能硫脲，从相同的起始原料合成了 4-取代 1,4-二氢吡啶的两种对映体。
• Enantioselective Organocatalytic Aza-Ene-Type Domino Reaction Leading to 1,4-Dihydropyridines
  作者：Artur Noole、Maria Borissova、Margus Lopp、Tõnis Kanger

  DOI：10.1021/jo200095e

  日期：2011.3.18

  A new general methodology was developed to access highly enantiomerically enriched 1,4-dihydropyridines (DHPs) 3 via an organocatalytic asymmetric aza-ene-type cascade reaction, cocatalyzed by (S)-diarylprolinol−TMS ether V and benzoic acid (BA). Both aliphatic and aryl enals 1 reacted smoothly with enaminones and β-enamino esters 2, affording highly functionalized 1,4-DHPs 3 in high enantioselectivities

  开发了一种新的通用方法，可通过（S）-二芳基脯氨醇-TMS醚V和苯甲酸（BA）共同催化的有机催化不对称氮杂-烯型级联反应获得高度对映体富集的1,4-二氢吡啶（DHPs）3。脂族和芳基烯醛1均与烯胺酮和β-烯胺酯2平稳反应，从而以高对映选择性和良好收率提供高度官能化的1,4-DHP 3。