(2,5-二甲氧基苄亚基)丙二酸二乙基酯 | 7324-87-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: (2,5-二甲氧基苄亚基)丙二酸二乙基酯
• 英文名称: diethyl 2,5-dimethoxybenzylidenemalonate
• 英文别名: diethyl 2-(2,5-dimethoxybenzylidene)malonate；Diethyl (2,5-dimethoxybenzylidene)malonate；diethyl 2-[(2,5-dimethoxyphenyl)methylidene]propanedioate
• CAS: 7324-87-0
• 化学式: C₁₆H₂₀O₆
• 分子量: 308.331
• InChiKey: SDKURJSMAYMSOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2,5-二甲氧基苄亚基)丙二酸二乙基酯 在 氢氧化钾 、 水 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 24.08h， 生成 7-甲氧基香豆素-3-羧酸
  参考文献：
  名称：

  A one-pot synthesis of coumarins from dipotassium O-methoxybenzylidenemalonates

  摘要：

  o-Methoxybenzylidenemalonates 1, which are available from o-methoxybenzaldehydes and diethyl malonate, were hydrolysed to the dipotassium malonates 2. Treatment of the salts 2 with trifluoroacetic acid-trifluoroacetic anhydride gave the title coumarins by a demethylative ring-closure reaction in 60-80% yield.

  DOI：

  10.1039/p19910000219

文献信息

• Enantiocontrolled Synthesis of β‐Branched α‐Amino Acids by Using Cu ^I ‐Catalyzed 1,4‐Addition of Glycine Imines to β‐Substituted <i>gem</i> ‐Diactivated Olefins
  作者：Jorge Hernández‐Toribio、Ramón Gómez Arrayás、Juan C. Carretero

  DOI：10.1002/chem.201100374

  日期：2011.5.27

  Branching out! The catalytic asymmetric conjugate addition of glycinate Schiff bases to β‐substituted gem‐diactivated Michael acceptors under proton transfer conditions gives a variety of β‐branched α‐amino acids (see scheme; Dpm=diphenylmethylene, EWG=electron‐withdrawing group) with excellent levels of diastereo‐ (typically syn/anti >90:10) and enantiocontrol (90–99 % ee).

  分支出！催化不对称共轭加成的甘氨酸Schiff碱至β -取代的宝石-diactivated质子转移条件下迈克尔受体给出的各种β-α支链氨基酸（参见方案; DPM =二苯基亚甲基，EWG =吸电子基团）具有优良的非对映体水平（通常是syn / anti > 90:10）和对映体控制（90–99％  ee）。
• Domino reactions of alkenyl p -benzoquinones: Access to aryl sulfide derivatives of coumarins
  作者：Shweta Bisht、Rama Krishna Peddinti

  DOI：10.1016/j.tet.2017.03.030

  日期：2017.5

  efficient domino approach has been developed for the synthesis of coumarin aryl sulfides utilizing alkenyl arenes derived electrophilic alkenyl p-benzoquinones through Michael addition of thiols followed by cyclization. The reaction proceeds regioselectively under mild conditions within short reaction time to afford the title products in good to excellent yields. This catalyst-free reaction has good

  已经开发了一种有效的多米诺方法，该方法利用烯基芳烃衍生的亲电烯基对苯并醌通过迈克尔加成硫醇然后环化来合成香豆素芳基硫化物。反应在温和的条件下在短的反应时间内在区域上进行选择性反应，以良好的收率得到标题产物。该无催化剂的反应具有良好的底物范围。
• Anthracene derivatives useful as intermediates in the preparation of daunomycinones
  申请人：Research Corporation

  公开号：EP0007400A1

  公开（公告）日：1980-02-06

  There is provided a novel method of synthesizing certain 3-(2',5'-dialkoxy- 4'-substituted phenyt) phthalides wherein the 4-substituent has para-directing properties. These compounds provide a novel and regiospecific synthesis of a 9-acetyl-6, 11-dihydroxy-4-methoxy- 7,8,9,10-tetrahydronaphthacene-5, 12-quinone (7,9- dideoxydaunomycinone) in particular, which is a known intermediate in the synthesis of daunomycinone. There is also provided a method of preparing analogs of 7,9- dideoxydaunomycinone. Daunomycinone is a known compound which is an intermediate in the preparation of the clinically accepted naturally-occurring antitumor antibiotics daunomycin and its derivative adriamycin.

  本发明提供了一种合成某些 3-(2',5'-二烷氧基-4'-取代苯基)邻苯二甲酸盐的新方法，其中 4-取代基具有对位定向特性。这些化合物为 9-乙酰基-6,11-二羟基-4-甲氧基-7,8,9,10-四氢萘-5,12-醌（7,9-二脱氧戴诺霉素酮）提供了一种新颖的特异性合成方法，尤其是合成戴诺霉素酮的已知中间体。此外，还提供了一种制备 7,9- 二脱氧达诺霉素酮类似物的方法。daunomycinone 是一种已知化合物，是制备临床上公认的天然抗肿瘤抗生素 daunomycin 及其衍生物 adriamycin 的中间体。
• Hydro-phosphorothiolation of Styrene and Cyclopropane with S-Hydrogen Phosphorothioates under Ambient Conditions
  作者：Biswajit Sarkar、Alakananda Hajra

  DOI：10.1021/acs.orglett.4c01586

  日期：2024.6.21

  A metal-free hexafluoroisopropanol-mediated hydro-phosphorothiolation of styrenes and donor–acceptor cyclopropanes with S-hydrogen phosphorothioates in a Markovnikov fashion has been developed under ambient reaction conditions to afford a library of S-alkyl phosphorothioates. Notably, this strategy provides a simple and efficient way to produce biologically significant kitazin and iprobenfos derivatives

  已经在环境反应条件下开发了一种无金属六氟异丙醇介导的苯乙烯和供体-受体环丙烷与S-氢硫代磷酸酯以马尔可夫尼科夫方式进行的氢硫代磷酸化反应，以提供S-烷基硫代磷酸酯库。值得注意的是，该策略提供了一种简单有效的方法来生产具有生物学意义的kitazin和异丙苯磷衍生物。机理研究表明该反应通过碳阳离子中间体进行。
• Synthesis and anticonvulsant activity of new 6-methyl-1-substituted-4,6-diazaspiro[2.4]heptane-5,7-diones
  作者：Xianran He、Guanpeng Qiu、Jin Yang、Yuling Xiao、Zhongyuan Wu、Guofu Qiu、Xianming Hu

  DOI：10.1016/j.ejmech.2010.05.034

  日期：2010.9

  In the present study on the development of new anticonvulsants, twenty new 6-methyl-1-substituted-4,6-diazaspiro[2.4]heptane-5,7-diones were synthesized and tested for anticonvulsant activity using the maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) screens. Their neurotoxicity was determined by the rotorod test. In this series, all of the alkyl- and aryl-substituted 5,5-cyclo-propanespirohydantoins showed more or less protection against MES and/or scPTZ models. The most active of the series was 6-methyl-1-(4-(methylsulfonyl)phenyl)-4,6-diazaspiro[2.4]heptane-5,7-dione (6t), which showed a MES ED50 value of 12.5 mg/kg in mice. The median toxic dose (TD50) was 310 mg/kg, providing compound 6t with a protection index (PI = TD50/ED50) of 24.8 in the MES test which is better than phenytoin. (C) 2010 Elsevier Masson SAS. All rights reserved.