Propanedioic acid, [(3,5-dimethoxyphenyl)methyl]-, dimethyl ester | 174754-65-5

• 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: Propanedioic acid, [(3,5-dimethoxyphenyl)methyl]-, dimethyl ester
• 英文别名: dimethyl 2-(3,5-dimethoxybenzyl)malonate
• CAS: 174754-65-5
• 化学式: C₁₄H₁₈O₆
• 分子量: 282.293
• InChiKey: GCRFOYGUEZWFFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  376.7±37.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.21
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Propanedioic acid, [(3,5-dimethoxyphenyl)methyl]-, dimethyl ester 在 potassium hydroxide 作用下， 以 水 为溶剂， 生成 3,5-二甲氧基苯基丙酸
  参考文献：
  名称：

  光柔性催化剂锌(II)卟啉促进红光促进自由基级联反应生成四氢化萘和二氢化萘

  摘要：

  [5,15-双(五氟苯基)-10,20-二苯基卟啉]锌(II) ( 1 )是一种金属卟啉衍生物，最近被我们小组报道为一种由蓝光LED驱动的高效光催化剂，被发现可以催化红光N -3-芳基丙酰氧基邻苯二甲酰亚胺与包括缺电子烯烃和炔烃在内的亲自由基化合物进行光促进（630 nm LED）自由基级联反应，从而获得一系列功能化的四氢化萘和二氢化萘衍生物。 1催化的自由基级联反应通过DMSO中的氧化猝灭循环发生，不需要牺牲电子供体，揭示了能够促进卟啉催化的独特溶剂效应。

  DOI：

  10.1021/acs.orglett.4c01112
• 作为产物：
  描述：

  丙二酸二甲酯 、 3,5-二甲氧基溴苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以68 %的产率得到Propanedioic acid, [(3,5-dimethoxyphenyl)methyl]-, dimethyl ester
  参考文献：
  名称：

  光柔性催化剂锌(II)卟啉促进红光促进自由基级联反应生成四氢化萘和二氢化萘

  摘要：

  [5,15-双(五氟苯基)-10,20-二苯基卟啉]锌(II) ( 1 )是一种金属卟啉衍生物，最近被我们小组报道为一种由蓝光LED驱动的高效光催化剂，被发现可以催化红光N -3-芳基丙酰氧基邻苯二甲酰亚胺与包括缺电子烯烃和炔烃在内的亲自由基化合物进行光促进（630 nm LED）自由基级联反应，从而获得一系列功能化的四氢化萘和二氢化萘衍生物。 1催化的自由基级联反应通过DMSO中的氧化猝灭循环发生，不需要牺牲电子供体，揭示了能够促进卟啉催化的独特溶剂效应。

  DOI：

  10.1021/acs.orglett.4c01112

文献信息

• Palladium catalyzed direct benzylation/allylation of malonates with alcohols – in situ C–O bond activation
  作者：Xueqin Cao、Yugen Zhang

  DOI：10.1039/c6gc00163g

  日期：——

  High step- and atomic-economy are the endless pursuit in organic and pharmaceutical synthesis. Herein, a new method for directly coupling of benzyl/allyl alcohols with malonates via palladium catalyzed Tsuji-Trost type...

  高阶和​​原子经济是有机和药物合成中无尽的追求。本文介绍了一种通过钯催化的Tsuji-Trost型直接将苄基/烯丙醇与丙二酸酯偶联的新方法...
• Meldrum's Acids as Acylating Agents in the Catalytic Intramolecular Friedel−Crafts Reaction
  作者：Eric Fillion、Dan Fishlock、Ashraf Wilsily、Julie M. Goll

  DOI：10.1021/jo0483724

  日期：2005.2.1

  dialkyl thioether, aryl methyl ether, aryl TIPS and TBDPS ethers, nitrile- and nitro-substituted aryls, alkyl and aryl halides) for a variety of 5-benzyl (enolizable Meldrum's acids) and 5-benzyl-5-substituted Meldrum's acids (quaternized Meldrum's acids), forming 1-indanones and 2-substituted-1-indanones, respectively, are delineated. This method was further applied to the synthesis of 1-tetralones,

  据报道，金属三氟甲磺酸盐催化的梅德鲁姆酸衍生物使芳烃分子内发生弗里德尔-克来福特酰化反应。Meldrum的酸易于制备，功能化，处理和纯化。深入研究了由苄基麦德鲁姆酸合成多取代的1-茚满酮的方法，结果表明，在温和条件下，多种催化剂均能有效容纳多种官能团。各种化合物的范围，局限性和官能团耐受性（末端烯烃和炔烃，缩酮，二烷基醚，二烷基硫醚，芳基甲基醚，芳基TIPS和TBDPS醚，腈和硝基取代的芳基，烷基和芳基卤化物） 5-苄基（可烯醇化的Meldrum's酸）和5-苄基-5-取代的Meldrum's酸（季铵化的Meldrum's酸），描绘了分别形成1-茚满酮和2-取代-1-茚满酮的化合物。该方法进一步应用于1-四氢萘酮，1-苯并亚砜和有效的乙酰胆碱酯酶抑制剂多奈哌齐的合成。通过竞争实验，确定了各种苯并环酮的环化率与环大小的关系：1-四酮类化合物的形成要比1-茚满酮和1-苯并亚砜的形成要快，而1-苯甲酮的成环作用要比1-茚满酮要快。
• Aryl–Allene Cyclization via a Hg(OTf)₂-Catalytic Pathway
  作者：Hirofumi Yamamoto、Maho Ueda、Naoto Yamasaki、Akiyoshi Fujii、Ikuo Sasaki、Kazunobu Igawa、Yusuke Kasai、Hiroshi Imagawa、Mugio Nishizawa

  DOI：10.1021/acs.orglett.6b01144

  日期：2016.6.17

  Hg(OTf)2-catalyzed aryl–allene cyclization accompanied by formation of a quaternary carbon center has been realized. Deuterium-labeling experiments and computational modeling were used to propose a novel catalytic pathway involving direct H-transfer from the aromatic ring to the vinyl mercury moiety followed by mercury 1,2-migration.

  Hg（OTf）2催化的芳基-亚芳基环化反应伴随形成季碳中心。氘标记实验和计算模型被用来提出一种新颖的催化途径，涉及直接H从芳环到乙烯基汞部分的H转移，然后汞1,2-迁移。
• A Carbaboranylmercuric Salt Catalyzed Reaction; Highly Regioselective Cycloisomerization of 1,3-Dienes
  作者：Hirofumi Yamamoto、Ikuo Sasaki、Shinya Shiomi、Naoto Yamasaki、Hiroshi Imagawa

  DOI：10.1021/ol300678r

  日期：2012.5.4

  The combination of carbaboranylmercuric chloride (new type of bulky Lewis acid) and silver triflate efficiently catalyzes cycloisomerization of 1, 3-dienes at room temperature. The catalytic system gives allyl-substituted azacycles and cycloalkanes in excellent yields with high to complete regioselectivity.
• Prediction of the Solvent Dependence of Enzymatic Prochiral Selectivity by Means of Structure-Based Thermodynamic Calculations
  作者：Tao Ke、Charles R. Wescott、Alexander M. Klibanov

  DOI：10.1021/ja952674t

  日期：1996.1.1

  A new, quantitative model is elaborated to rationalize the solvent dependence of enzymatic selectivity solely on the basis of the thermodynamics of substrate solvation. The model predicts that any type of the selectivity (defined as the ratio of k(cat)/K-M values) should be proportional to the ratio of the thermodynamic activity coefficients of the desolvated portions of the substrate(s) in the relevant transition state of the enzymatic reaction. The latter ratio is calculated by (i) determining the desolvated portion of the substrate in the transition state using molecular modeling based on the crystal structure of the enzyme, (ii) approximating this desolvated portion of the substrate by a distinct model compound, and (iii) calculating the activity coefficient of this model compound using the UNIFAC computer algorithm. In this study, the developed general model has been applied to, and verified with, prochiral selectivity of enzymes. Crystals (lightly cross-linked with glutaraldehyde) of gamma-chymotrypsin or subtilisin Carlsberg used as asymmetric catalysts in organic solvents almost quantitatively adhere to the predictions of the model in the acetylation of 2-substituted 1,3-propanediols. In contrast, little agreement between the predicted and observed solvent dependences of the prochiral selectivity has been obtained with lyophilized or acetone-precipitated chymotrypsin, thus confirming that the enzyme structure in such preparations (but not in crystals) is non-native.