diethyl 2-benzhydrylmalonate | 5292-54-6

• 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: diethyl 2-benzhydrylmalonate
• 英文别名: Benzhydryl-malonsaeure-diaethylester；2-benzhydrylmalonic acid diethyl ester；Diphenyl-methyl-malonsaeure-diaethylester；1,3-Diethyl 2-(diphenylmethyl)propanedioate；diethyl 2-benzhydrylpropanedioate
• CAS: 5292-54-6
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: PUHBCPOCAFDZJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 2-benzhydrylmalonate 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 2-Benzhydrylpropane-1,3-diol bismethanesulfonate
  参考文献：
  名称：

  通过3-碘丙基自由基的均相取代反应形成环丙烷的制备和速率研究

  摘要：

  用氢化锡还原2-取代的1，3-二碘丙烷衍生物，得到取代的环丙烷。该反应通过3-碘丙基的均质取代而发生，所述3-碘丙基在80℃下具有约5×10 5 s -1的速率常数。

  DOI：

  10.1016/s0040-4020(98)01144-2
• 作为产物：
  描述：

  (二苯基亚甲基)丙二酸二乙酯 在 乙醚 、 sodium 作用下， 生成 diethyl 2-benzhydrylmalonate
  参考文献：
  名称：

  Mediation of flowering by a calmodulin-dependent protein kinase

  摘要：

  A calmodulin-dependent protein kinase (MCK1) appeared important in regulating flowering in tobacco. The expression of modified MCK1 that lacks the C-terminal including calmodulin-binding domain upsets the flowering developmental program, leading to the abortion of flower primordia initiated on the main axis of the plant and, as well, caused the prolongation of the vegetative phase in axillary buds. The abortion process of flowers began first in the developing anthers and subsequently the entire flower senesces. In axillary buds the prolonged vegetative phase was characterized by atypical elongated, narrow, twisted leaves. These results suggested a role for calmodulin-dependent protein kinase homologs in mediating flowering.

  DOI：

  10.1007/bf02882393

文献信息

• A simple and efficient FeCl3-catalyzed direct alkylation of active methylene compounds with benzylic and allylic alcohols under mild conditions
  作者：Umasish Jana、Srijit Biswas、Sukhendu Maiti

  DOI：10.1016/j.tetlet.2007.04.017

  日期：2007.6

  A highly efficient FeCl3-catalyzed alkylation of various active methylene compounds with various benzylic or allylic alcohols under mild conditions has been developed. The reaction was carried out in the presence of a catalytic amount of anhydrous FeCl3 (10 mol %) under reflux in methylene chloride. High to excellent yields were obtained.

  已经开发了在温和条件下用各种苄基或烯丙基醇高效催化FeCl 3催化的各种活性亚甲基化合物的烷基化反应。该反应在催化量的无水FeCl 3（10mol％）的存在下在二氯甲烷中回流下进行。获得了高到优异的产率。
• Microwave-Irradiated Transition-Metal Catalysis: Rapid and Efficient Dehydrative Carbon-Carbon Coupling of Alcohols with Active Methylenes
  作者：Akio Baba、Srinivasarao Babu、Makoto Yasuda、Yasunori Tsukahara、Tomohisa Yamauchi、Yuji Wada

  DOI：10.1055/s-2008-1067020

  日期：2008.6

  transition-metal-catalyzed carbon-carbon coupling of a wide range of benzylic/allylic alcohols with β-diones, β-keto esters, and dialkyl malonates is reported. In a representative screening of transition-metal catalysts, salts of Zn, Cu, Fe, Sc, Ru, Pt, Ta, and Mo were found to furnish the coupling products. In light of the results obtained, among all of these catalysts copper(II) triflate was found to be relatively

  报道了一种快速且高效的合成微波辐照方案，用于过渡金属催化的各种苄醇/烯丙醇与 β-二酮、β-酮酯和丙二酸二烷基酯的碳-碳偶联。在对过渡金属催化剂的代表性筛选中，发现 Zn、Cu、Fe、Sc、Ru、Pt、Ta 和 Mo 的盐可以提供偶联产物。鉴于所获得的结果，在所有这些催化剂中，发现与其他催化剂相比，三氟甲磺酸铜 (II) 相对更有效，即使在反应性较低的苯甲醇或二酯的情况下也是如此。有趣的是，这些 MW 辐照反应是在或多或少 MW 透明的介质中进行的，例如甲苯，具有非常低的 tanδ，或在纯净条件下进行。
• Fe(ClO4)3·×H2O-Catalyzed direct C–C bond forming reactions between secondary benzylic alcohols with different types of nucleophiles
  作者：Ponnaboina Thirupathi、Sung Soo Kim

  DOI：10.1016/j.tet.2010.02.063

  日期：2010.4

  mild and efficient Fe(ClO4)3·×H2O-catalyzed direct C–C bond coupling reactions of 1,3-dicarbonyl compounds, electron-rich arenes and heteroarenes and 4-hydroxycoumarin with secondary benzylic alcohols have been described. The benzylation of electron-rich arenes and heteroarenes leads to the synthesis of bis-symmetrical triarylmethanes. The present method is also applied to synthesis of an anti-coagulant

  已经描述了温和有效的Fe（ClO 4）3 ·×H 2 O催化的1,3-二羰基化合物，富电子芳烃和杂芳烃以及4-羟基香豆素与仲苄醇的直接C-C键偶联反应。富电子芳烃和杂芳烃的苄基化导致双对称三芳基甲烷的合成。本发明的方法也适用于合成一个的抗-coagulant化合物，4-羟基-3-（1,2,3,4-四氢萘-1-基）-2- ħ从市场上可买到的底物中得到-铬-2--2-酮（香豆基（B）），产率为85％。该协议的优点是范围广，条件温和，使用廉价的催化剂以及操作简便，因为水是唯一的副产品。
• AlCl₃ catalyzed coupling of N-benzylic sulfonamides with 2-substituted cyanoacetates through carbon–nitrogen bond cleavage
  作者：Chen Hu、Gang Hong、Xiaofei Qian、Kwang Rim Kim、Xiaoyan Zhu、Limin Wang

  DOI：10.1039/c7ob01025g

  日期：——

  A new cross-coupling reaction of N-benzylic sulfonamides with 2-substituted cyanoacetates for the synthesis of 2-substituted benzylbenzene was reported. In the presence of the AlCl3, a broad range of N-benzylic sulfonamides reacted smoothly with 2-substituted cyanoacetates to afford structurally diverse benzylbenzenes in moderate to excellent yields. The conversion could be enlarged to gram-scale efficiently

  报道了一种新的N-苄基磺酰胺与2-取代的氰基乙酸酯的交叉偶联反应，用于合成2-取代的苄基苯。在AlCl3的存在下，各种各样的N-苄基磺酰胺与2-取代的氰基乙酸酯平稳反应，以中等至极好的收率提供结构多样的苄基苯。转换可以有效地扩大到克级。该方法的实用性在具有高抗炎活性的相关生物活性剂的合成中得到进一步证明。
• Efficient Nucleophilic Substitution of α-Aryl Alcohols with 1,3-Dicarbonyl Compounds Catalyzed by Tin Ion-Exchanged Montmorillonite
  作者：Makoto Onaka、Jiacheng Wang、Yoichi Masui

  DOI：10.1055/s-0030-1258567

  日期：2010.10

  Tin ion-exchanged montmorillonite demonstrated the high catalytic activity for the direct nucleophilic substitution of a hydroxyl group in α-aryl alcohols with various 1,3-dicarbonyl compounds including less acidic 1,3-diesters in crude solvents to afford the benzylated products accompanied by water.

  锡离子交换蒙脱石表现出对α-芳基醇中的羟基与各种1,3-双羰基化合物（包括酸性较弱的1,3-双酯）在粗溶剂中进行直接亲核取代反应的高催化活性，生成伴有水的苄基化产物。