(S)-3-(2-methoxyphenyl)-4-nitro-1-phenylbutan-1-one | 77670-27-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (S)-3-(2-methoxyphenyl)-4-nitro-1-phenylbutan-1-one
• 英文别名: 3-(2-methoxyphenyl)-4-nitro-1-phenylbutan-1-one；(3S)-3-(2-methoxyphenyl)-4-nitro-1-phenylbutan-1-one
• CAS: 77670-27-0
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: UQGAMRPGYAHNEB-CQSZACIVSA-N

物化性质

• 沸点：
  484.4±45.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二苯甲酰基甲烷 在 普瑞巴林杂质D 、 水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 均三甲苯 为溶剂， 反应 97.0h， 生成 (S)-3-(2-methoxyphenyl)-4-nitro-1-phenylbutan-1-one
  参考文献：
  名称：

  1,3-丙二酮与（E）-2-（2-硝基乙烯基）苯酚的有机催化不对称迈克尔/半缩酮化/酰基转移反应

  摘要：

  公开了（E）-2-（2-硝基乙烯基）苯酚和1，3-丙二酮之间的有机催化不对称级联迈克尔/半缩酮化/酰基转移反应。发现金鸡纳生物碱衍生的双官能硫脲催化剂对于该反应是最有效的，并以中等至良好的产率提供了具有良好至高对映选择性的所需产物。

  DOI：

  10.1039/c8ob01771a

文献信息

• High pressure-assisted low-loading asymmetric organocatalytic conjugate addition of nitroalkanes to chalcones
  作者：Agnieszka Cholewiak、Kamil Adamczyk、Michał Kopyt、Adrian Kasztelan、Piotr Kwiatkowski

  DOI：10.1039/c8ob00561c

  日期：——

  to 9 kbar) allows for relatively fast (1–5 h) and highly enantioselective 1,4-addition of nitromethane and 2-nitropropane to chalcones at room temperature with substantial reduction of catalyst loading (0.2–1 mol% of cinchona alkaloid-based thioureas and squaramides). Various γ-nitroketones were obtained at 9 kbar with high yield and enantioselectivity (up to 98%), whereas in control experiments at atmospheric

  施加高压（最高9 kbar）可在室温下相对快速地（1-5小时）和硝基甲烷和2-硝基丙烷的对映体1,4-对映体选择性高的加成反应，同时大大降低了催化剂的负载量（0.2-1摩尔％的基于金鸡纳生物碱的硫脲和方酸酰胺）。在9 kbar下以高收率和对映选择性（高达98％）获得了各种γ-硝基酮，而在大气压下的对照实验中，通常在20 h后仅生成少量（<10％）的产物。
• The Catalytic Efficiency of Isosteviol Derived Bifunctional Primary Amine-Squaramide on Michael Additions of Acetophenone to Nitroalkenes
  作者：Yu-Xia Liu、Zhi-Wei Ma、Chuan-Chuan Wang、Qian Li、Wen-Peng Mai

  DOI：10.2174/1570178619666220112124054

  日期：2022.8

  The isosteviol derived bifunctional primary amine-squaramide organocatalysts were applied in the Michael addition between nitroalkenes and acetophenone. The conjugate addition isomers of two configurations were observed with high yields (up to 93% yield) and good enantioselectivity (up to 91% ee) at room temperature.

  摘要：本文中使用了以异甘草酸为基础的双官能团一次胺-苯并二酮有机催化剂，在硝基烯烃和苯乙酮的Michael加成反应中应用。在室温下观察到两种构型的共轭加成异构体，收率高（高达93%）且对映选择性良好（高达91% ee）。
• Bifunctional chiral organocatalytic compound having excellent enantioselectivity, preparation method therefor, and method for producing non-natural gamma-amino acid from nitro compound by using same
  申请人：KOREA UNIVERSITY RESEARCH AND BUSINESS FOUNDATION

  公开号：US11465135B2

  公开（公告）日：2022-10-11

  The present invention relates to a bifunctional chiral organocatalytic compound having excellent enantioselectivity, a preparation method therefor, and a method for producing a non-natural gamma amino acid from a nitro compound by using the chiral organocatalytic compound. According to the present invention, the bifunctional chiral organocatalytic compound having excellent enantioselectivity can be easily synthesized, gamma-amino acids with high optical selectivity can be obtained at a high yield by an economical and convenient method using the chiral organocatalytic compound, and various (R)-configuration gamma-amino acids, which are not present in nature, can be produced with high optical purity in large quantities by using a small amount of a catalyst, and therefore, the present invention can be widely utilized in various industrial fields including the pharmaceutical industry.

  本发明涉及一种具有优异对映选择性的双功能手性有机催化化合物、其制备方法以及利用该手性有机催化化合物从硝基化合物制备非天然γ-氨基酸的方法。根据本发明，可以很容易地合成具有优异对映选择性的双功能手性有机催化化合物，并通过使用该手性有机催化化合物的经济、简便的方法高产率地获得具有高光学选择性的γ-氨基酸、而且只需使用少量催化剂，就能大量生产出自然界中不存在的各种(R)构型γ-氨基酸，且光学纯度高，因此本发明可广泛应用于包括制药业在内的各种工业领域。
• BIFUNCTIONAL CHIRAL ORGANOCATALYTIC COMPOUND HAVING EXCELLENT ENANTIOSELECTIVITY, PREPARATION METHOD THEREFOR, AND METHOD FOR PRODUCING NON-NATURAL GAMMA-AMINO ACID FROM NITRO COMPOUND BY USING SAME
  申请人：KOREA UNIVERSITY RESEARCH AND BUSINESS FOUNDATION

  公开号：US20200406243A1

  公开（公告）日：2020-12-31

  The present invention relates to a bifunctional chiral organocatalytic compound having excellent enantioselectivity, a preparation method therefor, and a method for producing a non-natural gamma amino acid from a nitro compound by using the chiral organocatalytic compound. According to the present invention, the bifunctional chiral organocatalytic compound having excellent enantioselectivity can be easily synthesized, gamma-amino acids with high optical selectivity can be obtained at a high yield by an economical and convenient method using the chiral organocatalytic compound, and various (R)-configuration gamma-amino acids, which are not present in nature, can be produced with high optical purity in large quantities by using a small amount of a catalyst, and therefore, the present invention can be widely utilized in various industrial fields including the pharmaceutical industry.