isopropyl 3-nitro-2-phenylpropanoate | 1070238-07-1

• 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: isopropyl 3-nitro-2-phenylpropanoate
• 英文别名: (S)-isopropyl 3-nitro-2-phenylpropanoate；propan-2-yl (2S)-3-nitro-2-phenylpropanoate
• CAS: 1070238-07-1
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: ICCZQFXZRIBZMY-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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 在 4-二甲氨基吡啶 、 [Ir(1,5-cyclooctadiene)((tBu)C7H10NOP(tBu))] tetrakis(3,5-bis(trifluoromethyl)phenyl)borate 、 氢气 、 甲基磺酰氯 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 20.0~70.0 ℃ 、5.07 MPa 条件下， 反应 96.0h， 生成 isopropyl 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 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.