methyl 1-(1-(2-bromophenyl)-2-nitroethyl)-2-oxocyclopentanecarboxylate | 1092784-93-4

• 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: methyl 1-(1-(2-bromophenyl)-2-nitroethyl)-2-oxocyclopentanecarboxylate
• 英文别名: (2R,3S)-methyl-1-(1-(2-bromophenyl)-2-nitroethyl)-2-oxocyclopentanecarboxylate
• CAS: 1092784-93-4
• 化学式: C₁₅H₁₆BrNO₅
• 分子量: 370.2
• InChiKey: BPJNGLTWOJRACH-XHDPSFHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  86.51
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1-溴-2-(2-硝基乙烯基)苯 、 2-甲氧羰基环戊酮 在 (4S,5S)-2-[3,5-bis[(4S,5S)-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl]phenyl]-4,5-diphenyl-4,5-dihydro-1H-imidazole 作用下， 以 甲苯 为溶剂， 反应 45.0h， 以93%的产率得到methyl 1-(1-(2-bromophenyl)-2-nitroethyl)-2-oxocyclopentanecarboxylate
  参考文献：
  名称：

  C3-Symmetric chiral trisimidazoline: the role of a third imidazoline and its application to the nitro Michael reaction and the α-amination of β-ketoesters

  摘要：

  We describe the necessity of the C-3-symmetry and the role of a third imidazoline of trisimidazoline 3, which was recently developed by us as a new entry of organocatalyst. The utility of 3 as a Bronsted base catalyst in the nitro Michael reaction and the alpha-amination of beta-ketoesters was shown, and the re-cyclability of the catalyst was also demonstrated. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.005

文献信息

• 2-Azanorbornane-Based Amino Alcohol Organocatalysts for Asymmetric Michael Reaction of β-Keto Esters with Nitroolefins
  作者：Rei Togashi、Madhu Chennapuram、Chigusa Seki、Yuko Okuyama、Eunsang Kwon、Koji Uwai、Michio Tokiwa、Mitsuhiro Takeshita、Hiroto Nakano

  DOI：10.1002/ejoc.201900308

  日期：2019.6.30

  A highly enantioselective Michael addition of β‐keto esters to nitroolefins was carried out using newly designed optically active 2‐azanorbornane‐based amino alcohol organocatalysts to produce the corresponding chiral Michael adducts in good chemical yields (up to 99 %) and stereoselectivities (up to dr = 91:9, up to 91 % ee).

  使用新设计的光学活性的基于2-氮杂降冰片烷的氨基醇有机催化剂，对β-酮酯向硝基烯烃进行了高对映选择性的迈克尔加成反应，从而以良好的化学收率（高达99％）和立体选择性（高达dr = 91：9，最高可达91％ee）。
• Fine‐Tunable Organocatalysts Bearing Multiple Hydrogen‐Bonding Donors for Construction of Adjacent Quaternary and Tertiary Stereocenters via a Michael Reaction
  作者：Zhi‐Hai Zhang、Xiu‐Qin Dong、Dong Chen、Chun‐Jiang Wang

  DOI：10.1002/chem.200801420

  日期：2008.10.10