dimethyl (Z)-2-(2-nitrophenoxy)-2-butenedioate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl (Z)-2-(2-nitrophenoxy)-2-butenedioate
• 英文别名: dimethyl 2-(2-nitrophenoxy)fumarate；dimethyl (Z)-2-(2-nitrophenoxy)but-2-enedioate
• 化学式: C₁₂H₁₁NO₇
• 分子量: 281.222
• InChiKey: ATFHPGUZMFPNQQ-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl (Z)-2-(2-nitrophenoxy)-2-butenedioate 、 dimethyl (E)-2-(2-nitrophenoxy)-2-butenedioate 在 氯磺酸 作用下， 反应 6.0h， 以65%的产率得到8-nitro-4-oxo-4H-chromene-2-carboxylic acid
  参考文献：
  名称：

  EP1479667

  摘要：

  公开号：
• 作为产物：
  描述：

  丁炔二酸二甲酯 在 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 dimethyl (Z)-2-(2-nitrophenoxy)-2-butenedioate
  参考文献：
  名称：

  Stereoselective Conversion of Stabilized Phosphorus Ylides to Dialkyl 2-(2-Nitro-phenoxy)-2-butenedioates in the Presense of Silica Gel in Solvent-Free Conditions

  摘要：

  Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by 2-nitrophenol leads to vinyltriphenylphosphonium salts, which undergo a Michael addition reaction with a conjugate base to produce dialkyl 2-(2-nitro-phenoxy)-3-(triphenylphosphoranylidene)butanedioates. Silica-gel powder was found to catalyze the stereoselective conversion of dialkyl 2-(2-nitro-phenoxy)-3-(triphenylphosphoranylidene)butanedioates to dialkyl 2-(2-nitro-phenoxy)-2-butenedioates in solvent-free conditions under microwave (0.5 KW, 3 min) and thermal (90 degrees C, 60 min) conditions.

  DOI：

  10.1080/10426500600864346

文献信息

• Trimethylamine catalyzed stereoselective reaction between dimethyl acetylenedicarboxylate and phenols
  作者：Farough Nasiri、Bahareh Atashkar

  DOI：10.1007/s00706-008-0919-z

  日期：2008.10

  Stereoselective reaction of various substituted phenols with dimethyl acetylenedicarboxylate in the presence of a catalytic amount of aqueous trimethylamine solution in dichloromethane leads to dimethyl 2-phenoxymaleates in good to excellent yields under mild condition.

  在催化量的三甲胺水溶液在二氯甲烷中的存在下，各种取代的酚与乙炔二甲酸二甲酯的立体选择反应在温和的条件下以良好的产率产生了2-苯氧基马来酸二甲酯。
• An efficient and green approach for the synthesis of vinyl aryl ethers in the presence of guanidine hydrochloride
  作者：SEYED MOHAMMAD VAHDAT、ROBABEH BAHARFAR

  DOI：10.3906/kim-1002-24

  日期：——

  A stereoselective procedure for vinyl aryl ether bond formation by direct coupling of dialkyl acetylenedicarboxylates and substituted phenols or naphthols under mild reaction conditions has been developed. Using guanidine hydrochloride as a new catalyst and water-acetone as green solvent, dialkyl acetylenedicarboxylates were reacted with substituted phenols or naphthols in room temperature to produce vinyl aryl ethers in good to excellent yields.

  开发了一种立体选择性的程序，通过在温和反应条件下直接耦合二烷基炔二酸酯和取代酚或萘醇来形成烯基芳醚键。采用盐酸胍作为新催化剂，水-丙酮作为绿色溶剂，二烷基炔二酸酯在室温下与取代酚或萘醇反应，产率良好到优秀。
• Process for producing chromone compound
  申请人：Hibino Hiroaki

  公开号：US20050085664A1

  公开（公告）日：2005-04-21

  A process for producing a dicarboxylic acid compound represented by the formula (4): wherein R 1 and R 2 are the same or different and each represents lower alkyl and the wavy line indicates that this compound is the E- or Z-isomer or a mixture of them, characterized by reacting a compound represented by the formula (2): wherein R 1 , R 2 and the wavy line have the same meanings as the above, and one of X 2 and X 3 represents hydrogen and the other represents halogen, with nitrophenol represented by the formula (3): in the presence of a base; a process for producing a nitrochromone compound represented by the formula (5): wherein R 1 has the same meaning as the above, characterized by reacting the dicarboxylic acid compound or carboxylic acid thereof with an acid; a process for producing an aminochromone compound which comprises reducing the nitrochromone compound; and a process for producing an amidochromone compound which comprises acylating the aminochromone compound are provided.

  提供一种制备式（4）的二羧酸化合物的方法，其中R1和R2相同或不同，每个代表低级烷基，波浪线表示该化合物是E或Z异构体或它们的混合物，其特征在于将式（2）的化合物与硝基酚在碱的存在下反应，式中R1、R2和波浪线的含义与上述相同，X2和X3中的一个代表氢，另一个代表卤素；提供一种制备式（5）的硝基香豆素化合物的方法，其中R1的含义与上述相同，其特征在于将二羧酸化合物或其羧酸与酸反应；提供一种制备氨基香豆素化合物的方法，其包括还原硝基香豆素化合物；以及提供一种制备酰胺香豆素化合物的方法，其包括酰化氨基香豆素化合物。
• PROCESS FOR PRODUCING CHROMONE COMPOUND
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1479667A1

  公开（公告）日：2004-11-24

  A process for producing a dicarboxylic acid compound represented by the formula (4): wherein R1 and R2 are the same or different and each represents lower alkyl and the wavy line indicates that this compound is the E- or Z-isomer or a mixture of them, characterized by reacting a compound represented by the formula (2): wherein R1, R2 and the wavy line have the same meanings as the above, and one of X2 and X3 represents hydrogen and the other represents halogen, with nitrophenol represented by the formula (3): in the presence of a base; a process for producing a nitrochromone compound represented by the formula (5): wherein R1 has the same meaning as the above, characterized by reacting the dicarboxylic acid compound or carboxylic acid thereof with an acid; a process for producing an aminochromone compound which comprises reducing the nitrochromone compound; and a process for producing an amidochromone compound which comprises acylating the aminochromone compound are provided.

  一种生产由式(4)代表的二羧酸化合物的工艺： 其中 R1 和 R2 相同或不同，且各自代表低级烷基，波浪线表示该化合物为 E-或 Z-异构体或它们的混合物，其特征在于使式（2）所代表的化合物反应： 其中 R1、R2 和波浪线的含义与上述相同，X2 和 X3 中的一个代表氢，另一个代表卤素： 在碱存在下；生产式（5）代表的硝基色酮化合物的工艺： 其中 R1 的含义与上述相同，其特征在于使二羧酸化合物或其羧酸与酸反应；提供了一种生产氨基色素化合物的工艺，该工艺包括还原硝基色素化合物；以及一种生产氨基色素化合物的工艺，该工艺包括酰化氨基色素化合物。
• Process for Producing Chromone Compound
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2105431A1

  公开（公告）日：2009-09-30

  A process for producing a dihalosuccinic acid compound in which the proportion of a threo-dihalosuccinic acid compound is 70% or higher, which comprises adding a maleic acid compound to a halogenating agent.

  一种生产二卤代琥珀酸化合物的工艺，其中三卤代二卤代琥珀酸化合物的比例为 70% 或更高，该工艺包括在卤化剂中加入马来酸化合物。