methyl 2-(2-nitro-1-phenylethyl)-1-oxo-2,3-dihydro-1H-indene-2-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: methyl 2-(2-nitro-1-phenylethyl)-1-oxo-2,3-dihydro-1H-indene-2-carboxylate
• 英文别名: methyl 2-(2-nitro-1-phenylethyl)-3-oxo-1H-indene-2-carboxylate
• 化学式: C₁₉H₁₇NO₅
• 分子量: 339.348
• InChiKey: YYCSXRCDXUSUMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  1H-茚-2-甲酸,2,3-二氢-1-氧代-,甲酯 、 β-硝基苯乙烯 在 st-DNA 作用下， 以 aq. buffer 为溶剂， 反应 24.0h， 以87%的产率得到methyl 2-(2-nitro-1-phenylethyl)-1-oxo-2,3-dihydro-1H-indene-2-carboxylate
  参考文献：
  名称：

  1,4-Michael additions of cyclic-β-ketoesters catalyzed by DNA in aqueous media

  摘要：

  In this work, we describe the 1,4-Michael addition of the 1,3-dicarbonyl compounds to activated ethylenes under st-DNA catalysis in water. The reaction of the beta-ketoester 4 with nitroolefins and conjugated carbonyls proceeds quite well, whereas other less activated ethylenes exhibit low or null reactivity. The catalyst can be recovered and reused for several catalytic cycles without significantly diminishing its efficiency. These reactions are similarly catalyzed by GMP, methyl-adenine and ethyl guanine, which suggests that the catalytic activity of st-DNA could be associated to the basic nature of their nucleotides' integrants. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.catcom.2013.08.015

文献信息

• Asymmetric Michael Addition Mediated by Novel Cinchona Alkaloid-Derived Bifunctional Catalysts Containing Sulfonamides
  作者：Jie Luo、Li-Wen Xu、Robyn Aik Siew Hay、Yixin Lu

  DOI：10.1021/ol802486m

  日期：2009.1.15

  Novel cinchona alkaloid-derived bifunctional organocatalysts containing sulfonamide groups were utilized to promote Michael addition of bicyclic α-substituted β-ketoesters to nitroolefins. The desired Michael adducts with all-carbon quaternary centers were constructed in high yield and with excellent enantioselectivity, demonstrating the great potential of cinchona alkaloid-derived sulfonamides in

  新型的含有磺酰胺基的金鸡纳生物碱衍生的双官能有机催化剂被用于促进双环α-取代的β-酮酸酯的迈克尔加成至硝基烯烃。所需的具有全碳季中心的迈克尔加合物以高收率和优异的对映选择性构建，证明了金鸡纳生物碱衍生的磺酰胺在不对称催化中的巨大潜力。
• Hydrogen-Bond-Promoted C-C Bond-Forming Reaction: Catalyst-Free Michael Addition Reactions in Ethanol
  作者：Seiji Shirakawa、Shoichi Shimizu

  DOI：10.1055/s-2007-992377

  日期：——

  A practical protocol for catalyst-free Michael addition reactions in ethanol was developed. The reaction was promoted efficiently in alcohol without any additives, and the importance of hydrogen-bonding activation was suggested.

  开发了一种在乙醇中无需催化剂的迈克尔加成反应实用方案。该反应在无任何添加剂的醇中高效进行，并提示了氢键活化的重要性。
• <i>C</i>₃-Symmetric Chiral Trisimidazoline: Design and Application to Organocatalyst
  作者：Kenichi Murai、Shunsuke Fukushima、Shoko Hayashi、Yusuke Takahara、Hiromichi Fujioka

  DOI：10.1021/ol902958m

  日期：2010.3.5

  C3-symmetric chiral trisimidazoline was designed and synthesized as a new entry of organocatalyst with the concept of constructing C3-symmetric molecules with three C2-symmetric chiral components, and the application of this novel catalyst to asymmetric conjugate addition of β-ketoesters to nitroolefins was described.

  设计并合成C 3对称手性三咪唑啉作为有机催化剂的一个新入口，其概念是构建具有三个C 2对称手性组分的C 3对称分子，并将该新型催化剂用于β-酮酸酯的不对称共轭加成中描述了对硝基烯烃的“三聚体”。
• 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
• Ag(I)-Catalyzed Michael Additions of β-Ketoesters to Nitroalkenes in Water: Remarkable Effect of Water as a Reaction Medium on Reaction Rates
  作者：Shu Kobayashi、Seiji Shirakawa

  DOI：10.1055/s-2006-939709

  日期：2006.6

  AgOTf-PPh 3 complex-catalyzed Michael additions of β-ketoesters to nitroalkenes in water were performed. The system promotes the reaction efficiently only in water, and interestingly the reaction does not proceed well in organic solvents. In addition, this reaction system could be applied to catalytic asymmetric synthesis in water.

  进行了 AgOTf-PPh 3 配合物催化的 β-酮酯与水中硝基烯烃的迈克尔加成反应。该系统仅在水中有效地促进反应，有趣的是反应在有机溶剂中不能很好地进行。此外，该反应体系可应用于水中催化不对称合成。