methyl 1-(2-nitro-1-p-tolylethyl)-2-oxocyclopentanecarboxylate | 1223091-48-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl 1-(2-nitro-1-p-tolylethyl)-2-oxocyclopentanecarboxylate
• 英文别名: (1S)-1-[(1R)-1-(4-methylphenyl)-2-nitroethyl]-2-oxo-cyclopentanecarboxylic acid methyl ester；(2S,3R)-methyl 1-(2-nitro-1-p-tolylethyl)-2-oxocyclopentanecarboxylate；methyl (1S)-1-[(1R)-1-(4-methylphenyl)-2-nitroethyl]-2-oxocyclopentane-1-carboxylate
• CAS: 1223091-48-2
• 化学式: C₁₆H₁₉NO₅
• 分子量: 305.331
• InChiKey: HBUUQNISUVWZQP-CJNGLKHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-methyl-β-nitrostyrene 、 2-甲氧羰基环戊酮 在 C₃₈H₂₆Co₂N₂O₈*2H₂O 作用下， 反应 10.0h， 以93%的产率得到methyl 1-(2-nitro-1-p-tolylethyl)-2-oxocyclopentanecarboxylate
  参考文献：
  名称：

  双功能同双金属 Co2-Schiff 碱配合物催化 β-酮酯与硝基烯烃的不对称 1,4-加成反应

  摘要：

  描述了 β-酮酯与硝基烯烃的催化不对称 1,4-加成反应。2.5 mol% 的均双金属路易斯酸/Brønsted 碱双功能 Co2-Schiff 碱配合物以优异的产率（高达 99%）、非对映选择性和对映选择性（高达 >30:1 dr 和 98% ee）顺利促进反应。催化剂负载成功地降低到 0.1 mol%。机理研究表明，两个 Co 金属中心的分子内协同功能对于高催化活性和立体选择性很重要。

  DOI：

  10.3390/molecules15010532

文献信息

• Simple primary β-amino alcohols as organocatalysts for the asymmetric Michael addition of β-keto esters to nitroalkenes
  作者：Zubeda Begum、Haruka Sannabe、Chigusa Seki、Yuko Okuyama、Eunsang Kwon、Koji Uwai、Michio Tokiwa、Suguru Tokiwa、Mitsuhiro Takeshita、Hiroto Nakano

  DOI：10.1039/d0ra09041g

  日期：——

  Simple primary β-amino alcohols act as an efficient organocatalysts in the asymmetric Michael addition of β-keto esters with nitroalkenes affording highly pure chiral Michael adducts. Also, both enantiomers of the adducts were obtained, depending on the specific catalyst used and reaction temperature.

  简单的伯 β-氨基醇在 β-酮酯与硝基烯烃的不对称迈克尔加成中充当有效的有机催化剂，提供高纯度的手性迈克尔加合物。此外，根据所使用的具体催化剂和反应温度，获得了加合物的两种对映体。
• Sugar Based γ-Amino Alcohol Organocatalyst for Asymmetric Michael Addition of β-Keto Esters with Nitroolefins
  作者：Hiroto Nakano、Divakar Ganesan、Madhu Chennapuram、Zubeda Begum、Chigusa Seki、Yuko Okuyama、Eunsang Kwon、Koji Uwai、Michio Tokiwa、Suguru Tokiwa、Mitsuhiro Takeshita

  DOI：10.3987/com-19-14172

  日期：——

  Division of Sustainable and Environmental Engineering, Graduate School of Engineering, Muroran Institute of Technology, 27-1 Mizumoto-cho, Muroran 050-8585, E-mail: [e-mail] Tohoku Medical and Pharmaceutical University, 4-4-1 Komatsushima, Aoba-Ku, Sendai 981-8558, Japan, E-mail: [e-mail] Research and Analytical Center for Giant Molecules, Graduate School of Sciences

  室兰工业大学工学研究生院可持续与环境工学部，室兰水本町27-1 050-8585，电子邮件：[e-mail] 东北医科大学， 4-4-1 Komatsushima, Aoba-Ku, Sendai 981-8558, Japan, E-mail: [e-mail] 东北大学研究生院大分子研究和分析中心, 6-3 Aoba, Aramaki, Aoba-Ku, Sendai 980-8578, Japan, E-mail: [e-mail] Tokiwakai Group, 62 Numajiri Tsuduri-Chou Uchigo Iwaki 973-8053, Japan, E-mail: hisyo@tokiwa.或.jp
• 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）。
• Hexafluorobenzene: a powerful solvent for a noncovalent stereoselective organocatalytic Michael addition reaction
  作者：Alessandra Lattanzi、Claudia De Fusco、Alessio Russo、Albert Poater、Luigi Cavallo

  DOI：10.1039/c2cc17488j

  日期：——

  A dramatic enhancement of the diastereo- and enantioselectivity in the nitro-Michael addition reaction organocatalysed by a commercially available alpha,alpha-L-diaryl prolinol was disclosed when performing the reaction in unconventional hexafluorobenzene as a medium. DFT calculations were performed to clarify the origin of stereoselectivity and the role of C(6)F(6).

  当在非常规六氟苯作为介质中进行反应时，公开了由市售的α，α-L-二芳基脯氨醇有机催化的硝基-迈克尔加成反应中非对映选择性和对映选择性的显着提高。进行DFT计算以阐明立体选择性的起源和C（6）F（6）的作用。
• Synthesis of cinchona urea polymers using Yamamoto coupling and their application to asymmetric reaction
  作者：Mohammad Farhadur Rahman、Ikuhide Fujisawa、Naoki Haraguchi、Shinichi Itsuno

  DOI：10.1002/chir.23526

  日期：2023.3

  These polymers showed high activities as heterogeneous catalysts in asymmetric Michael reactions comparable with those of the corresponding monomeric catalyst in solution systems. Furthermore, the polymeric catalysts are easily recovered from their reaction mixtures due to their insolubility and can be reused several times without loss of catalytic activity.

  具有 3,5-二碘苯基部分的金鸡纳脲化合物经过 Yamamoto 偶联聚合反应得到手性脲聚合物。这些聚合物在不对称迈克尔反应中显示出作为多相催化剂的高活性，与溶液体系中相应的单体催化剂相当。此外，由于聚合物催化剂的不溶性，它们很容易从它们的反应混合物中回收，并且可以重复使用多次而不会损失催化活性。