(+)-methyl 2-carbomethoxy-4-nitro-3-(2-furyl)-butyrate

• 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: (+)-methyl 2-carbomethoxy-4-nitro-3-(2-furyl)-butyrate
• 英文别名: (R)-methyl 2-carbomethoxy-4-nitro-3-(2-furyl)-butyrate；dimethyl 2-(1-(furan-2-yl)-2-nitroethyl)malonate；dimethyl 2-(2-nitro-1-furylethyl)malonate；dimethyl (R)-2-(1-(2-furyl)-2-nitroethyl)malonate；dimethyl 2-[(1S)-1-(furan-2-yl)-2-nitroethyl]propanedioate
• 化学式: C₁₁H₁₃NO₇
• 分子量: 271.227
• InChiKey: PZQQTBCYVZWRML-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-(2-硝基乙烯基)呋喃 、 丙二酸二甲酯 在 C₄₆H₅₀N₆O₄ 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 以96%的产率得到(+)-methyl 2-carbomethoxy-4-nitro-3-(2-furyl)-butyrate
  参考文献：
  名称：

  Biscinchona alkaloids as highly efficient bifunctional organocatalysts for the asymmetric conjugate addition of malonates to nitroalkenes at ambient temperature

  摘要：

  The novel bifunctional bisalkaloids have been developed as highly efficient catalysts for the asymmetric conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes with low catalyst loading (1 mol %) at ambient temperature, providing the products with excellent enantioselectivities (up to 97% ee). Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.070

文献信息

• Chiral Cobalt(III) Tris(1,2-diamine) Catalysts That Incorporate Nitrogenous Base Containing Anions for the Bifunctional Activation of Nucleophiles and Electrophiles in Enantioselective Addition Reactions
  作者：Connor Q. Kabes、Reagan F. Lucas、Jack H. Gunn、John A. Gladysz

  DOI：10.1021/acscatal.1c01883

  日期：2021.7.2

  The lipophilic diastereomeric cobalt complexes Λ or Δ-[Co((S,S)-dpen)3]3+ 2Cl–BArf– (Λ or Δ-(S,S)-23+ 2Cl–BArf–; dpen/BArf– = 1,2-diphenylethylenediamine/B(3,5-C6H3(CF3)2)4–) catalyze a number of enantioselective C–H bond addition reactions in the presence of aliphatic tertiary amines, but pyridine and N,N-dimethylaniline are much less effective. However, when these bases are incorporated into counter

  亲脂性非对映钴配合物 Λ 或 Δ-[Co(( S , S )-dpen) 3 ] 3+ 2Cl – BAr f – (Λ 或 Δ-( S , S )- 2 3+ 2Cl – BAr f – ; dpen /BAr f – = 1,2-二苯基乙二胺/B(3,5-C 6 H 3 (CF 3 ) 2 ) 4 – ) 在脂肪族叔胺存在下催化许多对映选择性的 C–H 键加成反应，但吡啶和N ,N-二甲基苯胺的效果要差得多。然而，当这些碱以 Λ 或 Δ-( S , S )- 2 3+ 4 – Cl – BAr f – 的形式结合到抗衡阴离子 ( 4 – ) 中时，可以实现高度对映选择性的双功能催化剂。烟酸盐、异烟酸盐、相关磺酸盐和N , N-二甲氨基苯甲酸酯是有效的。6-氯烟酸盐提供较慢的速率和较低的ee值，而6-氨基烟酸盐提供较快的速率和较高的ee值。6-甲基、2-甲氧基和未取代的类似物提供中间结果
• In situ preparation of a multifunctional chiral hybrid organic–inorganic catalyst for asymmetric multicomponent reactions
  作者：Pilar García-García、Alexandre Zagdoun、Christophe Copéret、Anne Lesage、Urbano Díaz、Avelino Corma

  DOI：10.1039/c3sc22310h

  日期：——

  A chiral mesoporous organosilica material incorporating a urea based-cinchona derivative and propylamine groups was prepared by a co-condensation method. The multisite solid catalyst efficiently promoted the asymmetric multicomponent reaction of aldehydes, malonates and nitromethane.

  一种具有手性的中孔有机硅材料通过共凝聚方法制备，材料中包含基于尿素的金凤花衍生物和丙胺基团。该多位点固体催化剂有效促进了醛类、马来酸酯和亚硝基甲烷的非对称多组分反应。
• Mimicking Enzymes: Asymmetric Induction inside a Carbamate–Based Steroidal Cleft
  作者：Carmen Concellón、Judith Martín、Miguel Gallegos、Noé Fanjul-Mosteirín、Aurora Costales、Ángel Martín Pendás、Vicente del Amo

  DOI：10.1021/acs.orglett.9b01170

  日期：2019.6.7

  Cholic acid has been elaborated into a carbamate-based tripodal architecture, which is able to promote an asymmetric organic transformation inside its chiral cavity. The nature of this steroidal catalyst has been disclosed by quantum-chemical calculations. It comprises the preorganization and confinement of the reagents within the cavity of the steroid to form a supramolecular complex held together

  胆酸已被精制成基于氨基甲酸酯的三脚架结构，该结构能够促进手性腔内有机物的不对称转化。该类固醇催化剂的性质已经通过量子化学计算公开。它包括在类固醇腔内对试剂进行预组织和限制，以形成通过协作的H键接触将在一起的超分子复合物。该操作模式类似于某些酶的操作模式。
• An enantioselective Michael addition of malonate to nitroalkenes catalyzed by low loading demethylquinine salts in water
  作者：Fu-Xin Chen、Cheng Shao、Quan Wang、Pin Gong、Dong-Yan Zhang、Bang-Zhi Zhang、Rui Wang

  DOI：10.1016/j.tetlet.2007.09.168

  日期：2007.11

  An enantioselective Michael addition of malonate to nitroalkenes is efficiently catalyzed by low loading demethylquinine salts in water; the yield range from 49% to 93% and the ee up to 90%.

  水中低负荷的去甲基奎宁盐可有效催化对硝基烯烃中丙二酸酯的对映选择性迈克尔加成反应。收率范围从49％到93％，而ee则高达90％。
• Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives
  作者：Jinxing Ye、Darren J. Dixon、Peter S. Hynes

  DOI：10.1039/b508833j

  日期：——

  and evaluated for asymmetric organocatalytic activity in the dimethyl malonate Michael addition to beta-nitrostyrene; thiourea derivative was identified as the most effective bifunctional organic catalyst and found to induce high enantioselectivity in the malonate ester Michael addition reaction to a range of nitro olefins.

  合成了一个9-氨基（9-脱氧）表西金宁衍生物家族，该衍生物在9位具有一定范围的单-和双齿氢键供体基团，并评估了丙二酸二甲酯与β-硝基苯乙烯之间的不对称有机催化活性。 ; 硫脲衍生物被认为是最有效的双官能有机催化剂，并发现在丙二酸酯迈克尔加成反应中，对一系列硝基烯烃具有较高的对映选择性。