methyl 3-nitro-2-phenylpropanoate

• 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 3-nitro-2-phenylpropanoate
• 英文别名: methyl (2S)-3-nitro-2-phenylpropanoate
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: KLSGLTVMOJSDEE-SECBINFHSA-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 [Ir(1,5-cyclooctadiene)((tBu)C7H10NOP(tBu))] tetrakis(3,5-bis(trifluoromethyl)phenyl)borate 、 氢气 、 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 20.0~70.0 ℃ 、5.07 MPa 条件下， 反应 48.0h， 生成 methyl 3-nitro-2-phenylpropanoate
  参考文献：
  名称：

  First Iridium-Catalyzed Highly Enantioselective Hydrogenation of β-Nitroacrylates

  摘要：

  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.

  DOI：

  10.1021/acs.orglett.5b01758

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。
• Organocatalytic enantioselective Michael addition of a kojic acid derivative to nitro olefins
  作者：Jiyu Wang、Qing Zhang、Hui Zhang、Yujun Feng、Weicheng Yuan、Xiaomei Zhang

  DOI：10.1039/c2ob07192d

  日期：——

  By employing a chiral bifunctional thiourea–tertiary amine as catalyst, enantioselective Michael addition of a kojic acid derivative to nitro olefins was realised. The reactions afforded the products with good yields (up to 99%) in good enantioselectivities (up to 97% ee). In addition, the absolute configuration of one product was determined.

  通过采用手性双官能团 硫脲以叔胺为催化剂，实现了将曲酸衍生物对硝基烯烃的对映选择性迈克尔加成反应。反应提供了具有良好对映选择性（高达97％ee）的良好产率（高达99％）的产物。另外，确定一种产品的绝对构型。
• Stereoselective reaction of 2-carboxythioesters-1,3-dithiane with nitroalkenes: an organocatalytic strategy for the asymmetric addition of a glyoxylate anion equivalent
  作者：Elisabetta Massolo、Maurizio Benaglia、Andrea Genoni、Rita Annunziata、Giuseppe Celentano、Nicoletta Gaggero

  DOI：10.1039/c5ob00492f

  日期：——

  Under mild reaction conditions γ-nitro-β-aryl-α-keto esters with up to 92% ee were obtained, realizing a formal catalytic stereoselective conjugate addition of the glyoxylate anion synthon.

  在温和的反应条件下，可以获得高达92% ee的γ-硝基-β-芳基-α-酮酸酯，实现了甘氧酸阴离子合成的形式催化立体选择性共轭加成。
• Squaramide Organocatalyzed Addition of a Masked Acyl Cyanide to β-Nitrostyrenes
  作者：Alison P. Hart、Caroline J. DeGraw、Gavin J. Rustin、Matthew G. Donahue、Julie A. Pigza

  DOI：10.1021/acs.joc.3c01838

  日期：2023.12.1

  A method for the squaramide-organocatalyzed enantioselective addition of a silyl-protected masked acyl cyanide (MAC) reagent to various β-nitrostyrenes is described. Reactions are carried out in a freezer and provide products cleanly and in high enantioselectivities at very low catalyst loadings. Adducts are then unmasked, providing various oxidation state 3 functional groups, thereby highlighting

  描述了一种甲硅烷基保护的掩蔽酰基氰化物 (MAC) 试剂在方酰胺有机催化下对映选择性加成到各种 β-硝基苯乙烯上的方法。反应在冷冻机中进行，以非常低的催化剂负载量提供清洁且具有高对映选择性的产品。然后，加合物被揭开，提供各种氧化态 3 官能团，从而突出这些 MAC 试剂的实用性和制备 β-氨基酸的新策略。
• Organocatalytic Asymmetric Transferhydrogenation of β-Nitroacrylates: Accessing β²-Amino Acids
  作者：Nolwenn J. A. Martin、Xu Cheng、Benjamin List

  DOI：10.1021/ja8069852

  日期：2008.10.22

  We describe a highly efficient and enantioselective Hantzsch ester mediated conjugate reduction of beta-nitroacrylates that is catalyzed by a Jacobsen thiourea catalyst as a key step in a new route to optically active beta2-amino acids.