ethyl 2-carboethoxy-3-(1-nitromethyl)nonanoate | 1355991-88-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2-carboethoxy-3-(1-nitromethyl)nonanoate
• 英文别名: (S)-diethyl 2-(1-nitrooctan-2-yl)malonate
• CAS: 1355991-88-6
• 化学式: C₁₅H₂₇NO₆
• 分子量: 317.382
• InChiKey: FCDFINIJWFPJJM-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  22.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  95.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  1-nitro-1-octene 、 丙二酸二乙酯 在 (1R,2R)-N1-(5,7-bis(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)-N2,N2-dimethylcyclohexane-1,2-diamine 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以82%的产率得到ethyl 2-carboethoxy-3-(1-nitromethyl)nonanoate
  参考文献：
  名称：

  Chiral 2-aminobenzimidazole bifunctional organocatalysts: effect of di-CF3 and TFA on catalytic mechanisms

  摘要：

  (S,S)-trans-Cyclohexanediamine-5,7-di-CF3-benzimidazole (3b) was developed as a new chiral bifunctional organocatalyst and successfully applied to Michael addition of diethyl malonate to nitroolefins (up to 99%, 98% ee) under neutral condition. Systematic investigation on the catalytic mechanism revealed that the role of the guanidine moiety and the dimethylamine moiety in catalysts might be reversed with respect to Bronsted/Lewis acidic or basic functionalities, depending on the reaction conditions (neutral or TFA co-catalyst). Generally, di-CF3 group substituted 2-aminobenzimidazole catalysts in neutral condition and non-substituted 2-aminobenzimidazole catalysts in co-catalyst (TFA) condition give high chemical yield and enantioselectivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.021

文献信息

• Syntheses of Enantiopure Bifunctional 2-Guanidinobenzimidazole Cyclopentadienyl Ruthenium Complexes: Highly Enantioselective Organometallic Hydrogen Bond Donor Catalysts for Carbon–Carbon Bond Forming Reactions
  作者：Tathagata Mukherjee、Carola Ganzmann、Nattamai Bhuvanesh、John A. Gladysz

  DOI：10.1021/om500705s

  日期：2014.12.8

  aryl-substituted nitroalkenes). The dominant product configurations are identical, showing the chiral ruthenium center to have little influence. The free GBI-R ligand exhibits only modest activity. Unlike most transition-metal-catalyzed reactions, there is no direct interaction of the substrate with the ruthenium; rather, evidence is presented for “second coordination sphere promoted catalysis” mediated by

  NHR基团代替NH 2（R：a，CH 2 Ph; b，（S C）-CH（CH 3）Ph; c，（R C R C）-CH（CN）的2-Guanidinobenzimidazole（GBI）衍生物CH 2）4 CHNMe 2；d，（R C R C）-CH（CH 2）4 CH- NCH 2（CH 2）3 CH 2由2-氨基苯并咪唑按四个步骤制备）。与反应[（η 5 -C 5 H ^ 5）的Ru（CO）（NCCH 3）2 ] + PF 6 - （5 + PF 6 - ），得到手性的金属螯合物[（η 5 -C 5 H ^ 5）Ru（CO）（GBI -R）] + PF 6 –（6a – d + PF 6 –，39–77％），已通过NMR（1 H，13 C，31 P，19 F）和其他光谱。的二甲基氨基的钌，C构型非对映体含有复合6C + PF 6 -时氧化铝色谱分离（ř孺ř Ç ř Ç，> 99:01博士;小号孺ř