methyl 1-(2-nitro-1-p-tolylethyl)-2-oxocyclopentanecarboxylate | 1092784-90-1

• 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: (2R,3S)-methyl-1-(2-nitro-1-p-toluethyl)-2-oxocyclopentanecarboxylate；(2R,3S)-methyl 1-(2-nitro-1-p-tolylethyl)-2-oxocyclopentanecarboxylate；methyl (1R)-1-[(1S)-1-(4-methylphenyl)-2-nitroethyl]-2-oxocyclopentane-1-carboxylate
• CAS: 1092784-90-1
• 化学式: C₁₆H₁₉NO₅
• 分子量: 305.331
• InChiKey: HBUUQNISUVWZQP-XJKSGUPXSA-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：

  (E)-2-(4-methylphenyl)-1-nitroethene 、 2-甲氧羰基环戊酮 在 (S)-2-amino-N-(naphthalene-1-yl)-3,3-dimethylbutanamide 作用下， 以 水 为溶剂， 反应 48.0h， 以74%的产率得到methyl 1-(2-nitro-1-p-tolylethyl)-2-oxocyclopentanecarboxylate
  参考文献：
  名称：

  用于 β-酮酯与 β-硝基烯烃不对称迈克尔加成的氨基酰胺有机催化剂

  摘要：

  使用手性氨基酰胺有机催化剂尝试了β-酮酯与反式-β-硝基烯烃的不对称迈克尔加成，并以两种优异的方式提供了合成有用的手性迈克尔加合物。

  DOI：

  10.1246/bcsj.20180302

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。
• Enantioselective organocatalytic Michael reactions using chiral (<i>R</i>,<i>R</i>)-1,2-diphenylethylenediamine-derived thioureas
  作者：Jae Ho Shim、Min Ji Lee、Min Ho Lee、Byeong-Seon Kim、Deok-Chan Ha

  DOI：10.1039/d0ra03550e

  日期：——

  Although the Michael addition is a very well-known and widely applied reaction, cost-effective, metal-free, and readily prepared organic catalysts remain rare. A chiral, bifunctional, (R,R)-1,2-diphenylethylenediamine-derived thiourea organic catalyst was developed and applied to asymmetric Michael additions of nitroalkenes under neutral conditions. Generally, fluorine-substituted thiourea catalysts

  尽管迈克尔加成反应是一种众所周知且应用广泛的反应，但具有成本效益、不含金属且易于制备的有机催化剂仍然很少见。开发了一种手性、双功能、( R , R )-1,2-二苯基乙二胺衍生的硫脲有机催化剂，并将其应用于中性条件下硝基烯烃的不对称迈克尔加成。通常，氟取代的硫脲催化剂在中性条件下表现出高化学产率和对映选择性。温和的反应对许多官能团具有耐受性，并提供了良好的产率，以及迈克尔加合物的高非对映和对映选择性。通过合成生物活性化合物 ( R )-Phenibut 证明了转化的效用。
• 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。