benzyl 2-hydroxy-3-nitro-2-phenylpropanoate | 1070236-97-3

• 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 2-hydroxy-3-nitro-2-phenylpropanoate
• CAS: 1070236-97-3
• 化学式: C₁₆H₁₅NO₅
• 分子量: 301.299
• InChiKey: PDPXXDHKHCLHAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  89.67
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  benzyl 2-hydroxy-3-nitro-2-phenylpropanoate 在 [Ir(1,5-cyclooctadiene)((tBu)C7H10NOP(tBu))] tetrakis(3,5-bis(trifluoromethyl)phenyl)borate 、 palladium 10% on activated carbon 、 氢气 、 甲基磺酰氯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0~70.0 ℃ 、5.07 MPa 条件下， 反应 96.0h， 生成 benzyl (2S)-3-amino-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
• 作为产物：
  描述：

  苯甲醇 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲苯 为溶剂， 生成 benzyl 2-hydroxy-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

• Organocatalytic Enantioselective Michael Reaction of Malononitrile with β,β-Disubstituted Nitroalkenes
  作者：Shengwei Chen、Qinxin Lou、Yuyang Ding、Shasha Zhang、Wenhui Hu、Junling Zhao

  DOI：10.1002/adsc.201500079

  日期：2015.8.10

  optimized an enantioselective Michael reaction of malononitrile with β,β‐disubstituted nitroalkenes. This reaction was catalyzed by a cinchona alkaloid derived thiourea catalyst, producing products of high yields (up to 98 %) and stereoselectivities (up to 93 % ee). One of the adducts was used as an intermediate for the synthesis of dihydropyrrole derivative bearing a synthetically valuable quaternary chiral

  我们已经开发和优化了丙二腈与β，β-二取代硝基烯烃的对映选择性Michael反应。该反应由金鸡纳生物碱衍生的硫脲催化剂催化，产生高收率（最高98％）和立体选择性（最高ee 93％）的产物。其中一种加合物用作合成带有合成有价值的季手性中心的二氢吡咯衍生物的中间体。
• Copper-Catalyzed Cross-Dehydrogenative Coupling of α-Hydroxy Esters with Nitromethane
  作者：Jin Jiang、Lili Xiao

  DOI：10.1055/a-1539-9116

  日期：2021.11

  β-nitro-α-hydroxy esters were prepared via cross-dehydrogenative coupling reaction using α-hydroxy esters as hydroxy compounds and nitromethane as a nucleophile. The reaction is believed to undergo an oxidation of the hydroxy group and then an addition of the generated carbonyl group. It is an example of CDC reactions related to hydroxy compounds via carbonyl intermediates.

  开发了羟基化合物与亲核试剂的有效铜催化串联氧化/硝基醛醇反应。在这项工作中，β-硝基-α-羟基酯是通过交叉脱氢偶联反应制备的，使用α-羟基酯作为羟基化合物，硝基甲烷作为亲核试剂。据信该反应经历羟基的氧化，然后产生的羰基的加成。它是通过羰基中间体与羟基化合物相关的 CDC 反应的一个例子。
• Enantioselective addition of nitromethane to α-keto esters catalyzed by copper(<scp>ii</scp>)–iminopyridine complexes
  作者：Gonzalo Blay、Victor Hernández-Olmos、José R. Pedro

  DOI：10.1039/b716446g

  日期：——

  The copper complex of a chiral iminopyridine easily prepared from (R)-(-)-fenchone and picolylamine catalyzes the enantioselective Henry (nitroaldol) reaction between nitromethane and alpha-keto esters. Good yields and modest to good enantioselectivities are obtained for a wide range of alpha-keto esters, bearing aromatic, alkyl or alkenyl groups attached to the ketone carbonyl group.

  由（R）-（-）-甲酮和甲基吡啶胺容易制备的手性亚氨基吡啶的铜络合物催化硝基甲烷和α-酮酸酯之间的对映选择性亨利（硝基醛醇）反应。对于广泛的带有与羰基羰基相连的芳族，烷基或烯基的α-酮酯，可获得良好的收率和中等至良好的对映选择性。
• 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.