benzyl 3-nitro-2-phenylpropanoate | 1070237-98-7

• 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: benzyl 3-nitro-2-phenylpropanoate
• 英文别名: (S)-benzyl 3-nitro-2-phenylpropanoate；benzyl (2S)-3-nitro-2-phenylpropanoate
• CAS: 1070237-98-7
• 化学式: C₁₆H₁₅NO₄
• 分子量: 285.299
• InChiKey: ZBPSFTCXVMQMSQ-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 3-nitro-2-phenylpropanoate 在 10% Pd/C 、 氢气 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以81%的产率得到(S)-3-氨基-2-苯基-丙酸
  参考文献：
  名称：

  Organocatalytic Asymmetric Transferhydrogenation of β-Nitroacrylates: Accessing β²-Amino Acids

  摘要：

  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.

  DOI：

  10.1021/ja8069852
• 作为产物：
  描述：

  benzyl oxo(phenyl)acetate 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 96.0h， 生成 benzyl 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

• 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.
• 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.