diethyl [2-nitro-1-(thiophen-2-yl)ethyl]propanedioate | 1147762-88-6

• 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: diethyl [2-nitro-1-(thiophen-2-yl)ethyl]propanedioate
• 英文别名: ethyl 2-ethoxycarbonyl-4-nitro-3-(thien-2-yl)butyrate；Diethyl 2-(2-nitro-1-thiophen-2-ylethyl)propanedioate
• CAS: 1147762-88-6
• 化学式: C₁₃H₁₇NO₆S
• 分子量: 315.347
• InChiKey: KKUOFIAHIHDJBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl [2-nitro-1-(thiophen-2-yl)ethyl]propanedioate 在 iron(III) chloride 、 碘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 3.42h， 生成 diethyl 2-(2-oxo-2-(thiophen-2-yl)ethylidene)malonate
  参考文献：
  名称：

  Boron Trifluoride Mediated Ring-Opening Reactions of trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates. Synthesis of Aroylmethylidene Malonates as Potential Building Blocks for Heterocycles

  摘要：

  trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates, upon treatment with BF3 center dot OEt2, undergo ring-opening rearrangement and the Nef reaction to give aroylmethylidene malonates. The products are found to be potential precursors for heterocycles, such as imidazoles, quinoxalines, and benzo[1,4]thiazines.

  DOI：

  10.1021/jo402848v
• 作为产物：
  描述：

  2-硝基乙烯基噻吩 、 丙二酸二乙酯 在 calcined hydrotalcite 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以60%的产率得到diethyl [2-nitro-1-(thiophen-2-yl)ethyl]propanedioate
  参考文献：
  名称：

  One pot domino reaction accessing γ-nitroesters: synthesis of GABA derivatives

  摘要：

  γ-硝基酯通过一锅法多米诺过程合成。GABA衍生物苯硫胺和巴克洛芬可以轻松获得。

  DOI：

  10.1039/c4nj01552e

文献信息

• Efficient Stereoselective Synthesis of Nitrocyclopropanes by the Oxidative Cyclization of Michael Adducts of Nitroolefins with Activated Methylene Compounds
  作者：Renhua Fan、Yang Ye、Weixun Li、Lingfei Wang

  DOI：10.1002/adsc.200800452

  日期：2008.11.3

  An efficient oxidative cyclopropanation of the Michael adducts of nitroolefins with activated methylene compounds by the combination of iodobenzene diacetate and tetrabutylammonium iodide is reported. Highly functionalized nitrocyclopropanes are synthesized in moderate to good yields via the Michael addition and cyclopropanation with high diastereoselectivity and enantioselectivity under mild conditions

  据报道，通过二碘代苯二乙酸酯和碘化四丁铵的结合，硝基烯烃的迈克尔加成物与活化的亚甲基化合物的有效氧化环丙烷化反应。在温和条件下，通过迈克尔加成和环丙烷化，以高非对映选择性和对映选择性，以中等至良好的产率合成了高度官能化的硝基环丙烷。
• Asymmetric urea compound and process for producing asymmetric compound by asymmetric conjugate addition reaction with the same as catalyst
  申请人：Takemoto Yoshiji

  公开号：US20060161006A1

  公开（公告）日：2006-07-20

  The present invention relates to a production method of asymmetric compound (IV) which includes conjugately adding nucleophilic reagent (III) to compound (II) in the presence of asymmetric urea compound (I). The present invention provides a non-metallic asymmetric catalyst capable of realizing a highly stereoselective asymmetric conjugate addition reaction in a high yield, and an advantageous production method of an asymmetric compound by an asymmetric conjugate addition reaction using the asymmetric catalyst. wherein X is an oxygen atom or a sulfur atom; C*, C** and C*** are asymmetric carbons; R 1 , R 2 , R 4 , R 5 , R 8 , R 9 and R 10 are each a lower alkyl group optionally having substituent(s) and the like, or R 4 and R 5 and the like in combination optionally form a homocyclic ring optionally having substituent(s) and the like; R 3 is an aryl group optionally having substituent(s) and the like; R 6 and R 7 are each a hydrogen atom and the like; Nu is —CR 16 (COR 17 )(COR 18 ) wherein R 16 , R 17 and R 18 are each a lower alkyl group optionally having substituent(s) and the like, and the like; and EWG is an electron withdrawing group.

  本发明涉及一种不对称化合物（IV）的生产方法，其中在不对称脲化合物（I）的存在下，将亲核试剂（III）共轭加到化合物（II）上。本发明提供了一种非金属不对称催化剂，能够在高产率下实现高度立体选择性的不对称共轭加成反应，并且提供了使用该不对称催化剂进行不对称共轭加成反应的有利生产方法。 其中，X是氧原子或硫原子；C*、C**和C***是不对称碳；R1、R2、R4、R5、R8、R9和R10分别是低级烷基，可选地具有取代基等，或者R4和R5等组合可选地形成具有取代基等的同环烷基；R3是芳基，可选地具有取代基等；R6和R7分别是氢原子等；Nu是—CR16（COR17）（COR18），其中R16、R17和R18分别是低级烷基，可选地具有取代基等；EWG是电子吸引基团。
• ASYMMETRIC UREA COMPOUND AND PROCESS FOR PRODUCING ASYMMETRIC COMPOUND BY ASYMMETRIC CONJUGATE ADDITION REACTION WITH THE SAME AS CATALYST
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1640361A2

  公开（公告）日：2006-03-29

  The present invention relates to a production method of asymmetric compound (IV) which includes conjugately adding nucleophilic reagent (III) to compound (II) in the presence of asymmetric urea compound (I). The present invention provides a non-metallic asymmetric catalyst capable of realizing a highly stereoselective asymmetric conjugate addition reaction in a high yield, and an advantageous production method of an asymmetric compound by an asymmetric conjugate addition reaction using the asymmetric catalyst. wherein X is an oxygen atom or a sulfur atom; C*, C** and C*** are asymmetric carbons; R1, R2, R4, R5, R8, R9 and R10 are each a lower alkyl group optionally having substituent(s) and the like, or R4 and R5 and the like in combination optionally form a homocyclic ring optionally having substituent(s) and the like; R3 is an aryl group optionally having substituent(s) and the like; R6 and R7 are each a hydrogen atom and the like; Nu is -CR16(COR17) (COR18) wherein R16, R17 and R18 are each a lower alkyl group optionally having substituent(s) and the like, and the like; and EWG is an electron withdrawing group.

  本发明涉及一种不对称化合物（IV）的生产方法，该方法包括在不对称脲化合物（I）存在下将亲核试剂（III）共轭加入到化合物（II）中。本发明提供了一种能够高产率地实现高立体选择性不对称共轭加成反应的非金属不对称催化剂，以及使用该不对称催化剂通过不对称共轭加成反应生产不对称化合物的有利方法。 其中 X 为氧原子或硫原子；C*、C**和 C*** 为不对称碳；R1、R2、R4、R5、R8、R9 和 R10 各为可选具有取代基等的低级烷基，或 R4 和 R5 等组合可选形成可选具有取代基等的均环；R3 是芳基，可选择具有取代基等；R6 和 R7 分别是氢原子等；Nu 是-CR16(COR17) (COR18) 其中 R16、R17 和 R18 分别是低级烷基，可选择具有取代基等；以及 EWG 是析电子基团。
• ASYMMETRIC UREA COMPOUNDS AND PROCESS FOR PRODUCING ASYMMETRIC COMPOUNDS BY ASYMMETRIC CONJUGATE ADDITION REACTION USING THE SAME AS CATALYST
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1640361B1

  公开（公告）日：2015-05-27
• US7632970B2
  申请人：——

  公开号：US7632970B2

  公开（公告）日：2009-12-15