Methyl α-phenyl-β-nitropropionate | 105732-42-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl α-phenyl-β-nitropropionate
• 英文别名: methyl 3-nitro-2-phenylpropanoate
• CAS: 105732-42-1
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: KLSGLTVMOJSDEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  苯甲酰甲酸甲酯 在 sodium tetrahydroborate 、 乙酸酐 、 三乙胺 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 99.0h， 生成 Methyl α-phenyl-β-nitropropionate
  参考文献：
  名称：

  现成的氢键催化剂可用于硝基烯烃的不对称转移氢化†

  摘要：

  本文着重于易于访问的内容 硫脲衍生自氨基酸的氢键催化剂，其位阻和电子特征受其在甲醇碳中心的取代度的调节。这些催化剂被用于硝基烯烃的不对称转移氢化，从而以高达99％的收率和86％的对映体过量提供手性产物。所提出的催化剂的作用方式得到机理研究的支持。

  DOI：

  10.1039/c1ob05059a

文献信息

• Readily available hydrogen bond catalysts for the asymmetric transfer hydrogenation of nitroolefins
  作者：Jakob F. Schneider、Markus B. Lauber、Vanessa Muhr、Domenic Kratzer、Jan Paradies

  DOI：10.1039/c1ob05059a

  日期：——

  focuses on readily accessible thiourea hydrogen bond catalysts derived from amino acids, whose steric and electronic features are modulated by their degree of substitution at the carbinol carbon center. These catalysts were applied in the asymmetric transfer hydrogenation of nitroolefins furnishing the chiral products in up to 99% yield and 86% enantiomeric excess. The proposed catalyst's mode of action

  本文着重于易于访问的内容 硫脲衍生自氨基酸的氢键催化剂，其位阻和电子特征受其在甲醇碳中心的取代度的调节。这些催化剂被用于硝基烯烃的不对称转移氢化，从而以高达99％的收率和86％的对映体过量提供手性产物。所提出的催化剂的作用方式得到机理研究的支持。
• A Facile Synthesis of α-Amino Esters via Reduction of α-Nitro Esters Using Ammonium Formate as a Catalytic Hydrogen Transfer Agent
  作者：Siya Ram、Richard E. Ehrenkaufer

  DOI：10.1055/s-1986-31497

  日期：——

  Various nitroesters 3 were selectively and rapidly reduced to their corresponding amino esters 4 in very good yield using anhydrous ammonium formate as a catalytic hydrogen transfer agent.

  各种硝基酯3在无水甲酸铵作为催化氢转移剂的条件下，选择性且快速地被还原为相应的氨基酯4，产率非常好。
• Pd-catalyzed asymmetric conjugate addition of arylboronic acids to 2-nitroacrylates: a facile route to β2-homophenylglycines
  作者：Andreas Petri、Oliver Seidelmann、Uwe Eilitz、Frank Leßmann、Stefan Reißmann、Volkmar Wendisch、Andrey Gutnov

  DOI：10.1016/j.tetlet.2013.11.015

  日期：2014.1

  Asymmetric conjugate addition of arylboronic acids to 2-nitroacrylamide in the presence of cationic palladium-Chiraphos complex proceeds with high yield and enantioselectivity (73-89% ee) using as low as 0.05-0.25 mol % of the catalyst. The adducts can be smoothly transformed into the corresponding beta(2)-homophenylglycines in two simple steps. (C) 2013 Elsevier Ltd. All rights reserved.
• First Iridium-Catalyzed Highly Enantioselective Hydrogenation of β-Nitroacrylates
  作者：Shengkun Li、Taifeng Xiao、Dangdang Li、Xumu Zhang

  DOI：10.1021/acs.orglett.5b01758

  日期：2015.8.7

  The first highly chemo- and enantioselective hydrogenation of beta-nitroacrylates was accomplished with an iridium catalyst (Ir-4) with yields and enantioselectivities of up to 96% and 98% ee, respectively. The resulting alpha chiral beta-nitro propionates are attractive building blocks for the synthesis of chiral beta(2)-amino acids, which are the core scaffolds of bioactive natural products, pharmaceuticals, and beta-peptides.