(R)-methyl 2-carbomethoxy-4-nitro-3-(1-naphthyl)-butyrate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-methyl 2-carbomethoxy-4-nitro-3-(1-naphthyl)-butyrate
• 英文别名: dimethyl 2-(2-nitro-1-α-naphthylethyl)malonate；dimethyl (R)-2-(1-(naphthalen-1-yl)-2-nitroethyl)malonate；dimethyl (R)-2-(1-(1-naphthyl)-2-nitroethyl)malonate；dimethyl 2-[(1R)-1-naphthalen-1-yl-2-nitroethyl]propanedioate
• 化学式: C₁₇H₁₇NO₆
• 分子量: 331.325
• InChiKey: UFFRGXPOHLKDMO-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(2-硝基乙烯基)萘 、 丙二酸二甲酯 在 C₄₆H₅₀N₆O₄ 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以99%的产率得到(R)-methyl 2-carbomethoxy-4-nitro-3-(1-naphthyl)-butyrate
  参考文献：
  名称：

  Biscinchona alkaloids as highly efficient bifunctional organocatalysts for the asymmetric conjugate addition of malonates to nitroalkenes at ambient temperature

  摘要：

  The novel bifunctional bisalkaloids have been developed as highly efficient catalysts for the asymmetric conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes with low catalyst loading (1 mol %) at ambient temperature, providing the products with excellent enantioselectivities (up to 97% ee). Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.070

文献信息

• Chiral Cobalt(III) Tris(1,2-diamine) Catalysts That Incorporate Nitrogenous Base Containing Anions for the Bifunctional Activation of Nucleophiles and Electrophiles in Enantioselective Addition Reactions
  作者：Connor Q. Kabes、Reagan F. Lucas、Jack H. Gunn、John A. Gladysz

  DOI：10.1021/acscatal.1c01883

  日期：2021.7.2

  The lipophilic diastereomeric cobalt complexes Λ or Δ-[Co((S,S)-dpen)3]3+ 2Cl–BArf– (Λ or Δ-(S,S)-23+ 2Cl–BArf–; dpen/BArf– = 1,2-diphenylethylenediamine/B(3,5-C6H3(CF3)2)4–) catalyze a number of enantioselective C–H bond addition reactions in the presence of aliphatic tertiary amines, but pyridine and N,N-dimethylaniline are much less effective. However, when these bases are incorporated into counter

  亲脂性非对映钴配合物 Λ 或 Δ-[Co(( S , S )-dpen) 3 ] 3+ 2Cl – BAr f – (Λ 或 Δ-( S , S )- 2 3+ 2Cl – BAr f – ; dpen /BAr f – = 1,2-二苯基乙二胺/B(3,5-C 6 H 3 (CF 3 ) 2 ) 4 – ) 在脂肪族叔胺存在下催化许多对映选择性的 C–H 键加成反应，但吡啶和N ,N-二甲基苯胺的效果要差得多。然而，当这些碱以 Λ 或 Δ-( S , S )- 2 3+ 4 – Cl – BAr f – 的形式结合到抗衡阴离子 ( 4 – ) 中时，可以实现高度对映选择性的双功能催化剂。烟酸盐、异烟酸盐、相关磺酸盐和N , N-二甲氨基苯甲酸酯是有效的。6-氯烟酸盐提供较慢的速率和较低的ee值，而6-氨基烟酸盐提供较快的速率和较高的ee值。6-甲基、2-甲氧基和未取代的类似物提供中间结果
• Bis(imidazolidine)pyridine‐CoCl ₂ : A Novel, Catalytically Active Neutral Complex for Asymmetric Michael Reaction of 1,3‐Carbonyl Compounds with Nitroalkenes
  作者：Takayoshi Arai、Yuko Iimori、Mayu Shirasugi、Ryota Shinohara、Yuri Takagi、Takumi Suzuki、Junma Ma、Satoru Kuwano、Hyuma Masu

  DOI：10.1002/adsc.201900421

  日期：2019.8.21

  A neutral bis(imidazolidine)pyridine (PyBidine)‐CoCl2 complex showed catalytic activity for the Michael reaction of malonates with nitroalkenes. The results indicated that a weak amine base aided enolate formation from the neutral complex, in which the N−H proton of the imidazolidine ligand played a significant role.

  中性双（咪唑烷）吡啶（PyBidine）-CoCl 2络合物显示出对丙二酸酯与硝基烯烃的迈克尔反应的催化活性。结果表明，弱胺碱有助于中性配合物形成烯醇化物，其中咪唑烷配体的NH质子起着重要作用。
• An enantioselective Michael addition of malonate to nitroalkenes catalyzed by low loading demethylquinine salts in water
  作者：Fu-Xin Chen、Cheng Shao、Quan Wang、Pin Gong、Dong-Yan Zhang、Bang-Zhi Zhang、Rui Wang

  DOI：10.1016/j.tetlet.2007.09.168

  日期：2007.11

  An enantioselective Michael addition of malonate to nitroalkenes is efficiently catalyzed by low loading demethylquinine salts in water; the yield range from 49% to 93% and the ee up to 90%.

  水中低负荷的去甲基奎宁盐可有效催化对硝基烯烃中丙二酸酯的对映选择性迈克尔加成反应。收率范围从49％到93％，而ee则高达90％。
• Solvent free enantioselective catalysis with chiral cobalt(<scp>iii</scp>) Werner complexes <i>via</i> ball milling
  作者：Connor Q. Kabes、Bailey L. Jameson、John A. Gladysz

  DOI：10.1039/d1nj03698j

  日期：——

  Enantioselective additions of malonate esters to nitroalkenes can be catalyzed by a variety of salts of chiral cobalt(III) trications [Co(1,2-diamine)3]3+ in the presence of nitrogen donor bases in acetone. Catalysts that feature enantiopure 1,2-diphenylethylenediamine are particularly effective, and the base can also be incorporated into one of the counter anions, for example a (substituted) nicotinate

  丙二酸酯对硝基烯烃的对映选择性加成可以通过各种手性钴 ( III ) 三化 [Co(1,2-二胺) 3 ] 3+盐催化，在丙酮中存在氮供体碱。以对映体纯 1,2-二苯基乙二胺为特征的催化剂特别有效，并且碱也可以结合到抗衡阴离子之一中，例如（取代的）烟酸盐。这项研究表明，这种添加可以在无溶剂条件下进行，并使用球磨减少反应时间，进一步增强了这一大类地球丰富金属催化剂的“绿色”证书。探讨了各种反应变量的影响（碱、反阴离子、负载、时间、球的数量、等），并将优化的条件应用于 12 种硝基烯烃，产品的平均收率和 ee 值分别为 89% 和 74%。对映选择性似乎略低于溶液 (0 °C) 中的类似反应，并讨论了可能的因素和补救措施。
• Biscinchona alkaloids as highly efficient bifunctional organocatalysts for the asymmetric conjugate addition of malonates to nitroalkenes at ambient temperature
  作者：Fei Li、Ying-Zi Li、Zhen-Shan Jia、Ming-Hua Xu、Ping Tian、Guo-Qiang Lin

  DOI：10.1016/j.tet.2011.08.070

  日期：2011.12

  The novel bifunctional bisalkaloids have been developed as highly efficient catalysts for the asymmetric conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes with low catalyst loading (1 mol %) at ambient temperature, providing the products with excellent enantioselectivities (up to 97% ee). Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.