2-[(4-methoxyphenyl)methyl]succinic acid dimethyl ester | 792942-87-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[(4-methoxyphenyl)methyl]succinic acid dimethyl ester
• 英文别名: 2-(4-methoxybenzyl)succinic acid dimethyl ester；dimethyl 2-(4-methoxybenzyl)succinate；(4-methoxy-benzyl)-succinic acid dimethyl ester；(4-Methoxy-benzyl)-bernsteinsaeure-dimethylester；<4-Methoxy-benzyl>-bernsteinsaeure-dimethylester；1,4-Dimethyl 2-[(4-methoxyphenyl)methyl]butanedioate；dimethyl 2-[(4-methoxyphenyl)methyl]butanedioate
• CAS: 792942-87-1
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: PEISRBZCWDSMKY-UHFFFAOYSA-N

物化性质

• 沸点：
  363.7±32.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(4-methoxyphenyl)methyl]succinic acid dimethyl ester 在 氢溴酸 作用下， 生成 (4-hydroxybenzyl)-succinic acid
  参考文献：
  名称：

  Factor VIIa inhibitors: Improved pharmacokinetic parameters

  摘要：

  Efforts to improve the potency and pharmacokinetic properties of small molecule factor VIIa inhibitors are described. Small structural modifications to existing leads allow the modulation of half-life and clearance, potentially making these compounds suitable candidates for drug development. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.037
• 作为产物：
  描述：

  衣康酸二甲酯 生成 2-[(4-methoxyphenyl)methyl]succinic acid dimethyl ester
  参考文献：
  名称：

  Factor VIIa inhibitors: Improved pharmacokinetic parameters

  摘要：

  Efforts to improve the potency and pharmacokinetic properties of small molecule factor VIIa inhibitors are described. Small structural modifications to existing leads allow the modulation of half-life and clearance, potentially making these compounds suitable candidates for drug development. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.037

文献信息

• Benzyl radical addition reaction through the homolytic cleavage of a benzylic C–H bond
  作者：Masafumi Ueda、Eiko Kondoh、Yuta Ito、Hiroko Shono、Maiko Kakiuchi、Yuki Ichii、Takahiro Kimura、Tetsuya Miyoshi、Takeaki Naito、Okiko Miyata

  DOI：10.1039/c0ob01148g

  日期：——

  Direct generation of a benzyl radical by C–H bond activation of toluenes and the addition reaction of the resulting radical to an electron deficient olefin were developed. The reaction of dimethyl fumarate with toluene in the presence of Et3B as a radical initiator at reflux afforded 2-benzylsuccinic acid dimethyl ester in good yield.

  通过甲苯的C–H键活化直接生成苄基自由基，以及由此产生的自由基与缺电子烯烃的加成反应。的反应富马酸二甲酯 和 甲苯在Et 3 B作为自由基引发剂存在下进行回流2-苄基琥珀酸二甲酯 产量高。
• Smooth Photocatalyzed Benzylation of Electrophilic Olefins via Decarboxylation of Arylacetic Acids
  作者：Luca Capaldo、Luca Buzzetti、Daniele Merli、Maurizio Fagnoni、Davide Ravelli

  DOI：10.1021/acs.joc.6b00984

  日期：2016.8.19

  Arylacetic acids were used as sources of benzyl radicals under tetrabutylammonium decatungstate photocatalyzed conditions for the benzylation of electron-poor olefins. The reaction proceeds smoothly in a mixed aqueous medium (MeCN/H2O 2/1) in the presence of NaHCO3, NaClO4, and an electron transfer agent (biphenyl). The reaction tolerates a wide variety of functional groups on the aromatic ring (whether

  在四丁基铵去癸酸盐光催化条件下，丙烯酸被用作苄基的来源，用于贫电子烯烃的苄基化。在NaHCO 3，NaClO 4和电子转移剂（联苯）的存在下，反应在混合水性介质（MeCN / H 2 O 2/1）中平稳进行。该反应可耐受芳环上的各种官能团（无论是供电子还是吸电子），并可扩展为杂芳族类似物。烯烃具有自由基陷阱和电子受体的双重作用。本方法还可扩展至芳基丙酸（包括非甾体抗炎药布洛芬和氟比洛芬），以及扁桃酸衍生物。
• Rhodium-catalysed addition of organotrialkoxysilanes to α-substituted acrylic esters
  作者：Jonathan D. Hargrave、Jennifer Herbert、Gerwyn Bish、Christopher G. Frost

  DOI：10.1039/b606977k

  日期：——

  The cationic rhodium complex [Rh(cod)2][BF4] effectively catalyses the 1,4-addition of organotrialkoxysilanes to alpha-substituted acrylic esters. The reactions are promoted by heating in an oil-bath or more conveniently in a microwave reactor allowing rapid access to a useful range of functionalised products including 2-alkyl succinates and alpha-amino acid derivatives.

  阳离子铑配合物[Rh（cod）2] [BF4]有效地催化有机三烷氧基硅烷与α-取代的丙烯酸酯的1,4-加成反应。通过在油浴中加热或更方便地在微波反应器中加热来促进反应，从而允许快速获得有用范围的官能化产物，包括琥珀酸2-烷基酯和α-氨基酸衍生物。
• Rhodium-Catalysed 1,4-Additions in Water: Synthesis of Succinic Esters and β²-Amino Acid Derivatives
  作者：Christopher Frost、Kelly Wadsworth、Frances Wood、Christopher Chapman

  DOI：10.1055/s-2004-830880

  日期：——

  The rhodium-catalysed addition of boronic acids to α-substituted activated alkenes proceeds smoothly in water resulting in a unique synthesis of both succinic esters and β 2 -amino acid derivatives.

  硼酸在铑催化下加成到 α-取代的活化烯烃中，在水中顺利进行，从而形成琥珀酸酯和 β2-氨基酸衍生物的独特合成。
• Highly selective α-aryloxyalkyl C–H functionalisation of aryl alkyl ethers
  作者：Jonathan D. Bell、Iain Robb、John A. Murphy

  DOI：10.1039/d2sc04463c

  日期：——

  We report highly selective photocatalytic functionalisations of alkyl groups in aryl alkyl ethers with a range of electron-poor alkenes using an acridinium catalyst with a phosphate base and irradiation with visible light (456 nm or 390 nm). Experiments indicate that the reaction operates via direct single-electron oxidation of the arene substrate ArOCHRR′ to its radical cation by the excited state

  我们报告了使用具有磷酸盐基的吖啶催化剂和可见光（456 nm 或 390 nm）辐照，对芳基烷基醚中的烷基与一系列缺电子烯烃进行高选择性光催化官能化。实验表明该反应通过通过激发态有机光催化剂将芳烃底物ArOCHRR'直接单电子氧化为其自由基阳离子；随后，自由基阳离子中的 ArOC–H 去质子化，产生自由基 ArOC˙RR'。然后该自由基攻击亲电子试剂形成中间烷基自由基，该烷基自由基被还原以完成光催化循环。氧化步骤对活性芳烃 (ArOR) 的选择性超过其非活性对应物，随后甲氧基的去质子化提供 α-芳氧基烷基自由基，从而以良好到极好的收率产生范围广泛的功能化产品。