dimethyl 2-[1-(naphthalen-2-yl)ethyl]malonate | 142077-86-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dimethyl 2-[1-(naphthalen-2-yl)ethyl]malonate
• 英文别名: Dimethyl 2-(1-naphthalen-2-ylethyl)propanedioate
• CAS: 142077-86-9
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: OOVNBJUMBRKZAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  dimethyl 2-[1-(naphthalen-2-yl)ethyl]malonate 在 potassium acetate 作用下， 以 二甲基亚砜 为溶剂， 生成 methyl 3-(naphthalen-2-yl)butanoate
  参考文献：
  名称：

  Asymmetric palladium-catalyzed benzylic nucleophilic substitution: high enantioselectivity with the DUPHOS family ligands

  摘要：

  The asymmetric palladium-catalyzed benzylic reaction of 1-(2-naphthyl)ethyl acetate and its 6-methoxy substituted analogue with dimethyl malonate anion led to substitution products with up to 90% ee when the iPr-DUPHOS chiral ligand was used. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.032
• 作为产物：
  描述：

  2-乙烯基萘 、 丙二酸二甲酯 在 [Ir(cod)₂]SbF₆ 、 2,2'-双(二苯基磷)联苯 作用下， 以 氯苯 为溶剂， 以83 %的产率得到dimethyl 2-[1-(naphthalen-2-yl)ethyl]malonate
  参考文献：
  名称：

  铱催化的简单烯烃与丙二酰胺和丙二酸酯的分支选择性加氢烷基化反应

  摘要：

  我们报道了在中性反应条件下，铱催化的简单烯烃如脂肪族烯烃和芳香族烯烃与丙二酰胺和丙二酸酯的支链选择性加氢烷基化反应。各种带有溴、氯、酯、2-噻吩基羧酸酯、甲硅烷基和邻苯二甲酰亚胺基团的脂肪族烯烃和芳香族烯烃都被发现适用于这种加氢烷基化反应。该方法与Krapcho脱烷氧基羰基化相结合，实现了β-酰胺酯和丙二酸酯一锅法合成β-取代酰胺和酯。衍生自丙二酰胺的加氢烷基化产物适合进一步转化。微调的反应条件实现了使用相同试剂将加氢烷基化产物选择性转化为 1,3-二胺或单酰胺。氘标记实验和动力学同位素效应的测量表明，催化循环涉及可逆步骤，C-H 键的裂解不是决速步骤。密度泛函理论计算提供了对反应机制的深入了解，其中碳化步骤之后是 C-H 还原消除。

  DOI：

  10.1021/acs.joc.2c02599

文献信息

• Palladium-catalyzed substitution of esters of naphthylmethanols, 1-naphthylethanols, and analogues by sodium dimethyl malonate. Stereoselective synthesis from enantiomerically pure substrates
  作者：Jean-Yves Legros、Martial Toffano、Jean-Claude Fiaud

  DOI：10.1016/0040-4020(95)00061-c

  日期：1995.3

  The palladium-catalyzed substitution of carbonates of the titled alcohols was performed at lower temperature than the previously reported reaction of the corresponding acetates. The use of enantiomerically pure carbonates gave substitution products with overall retention of the configuration (up to 97%).

  钯催化的标题醇的碳酸酯的取代是在比先前报道的相应乙酸盐的反应更低的温度下进行的。对映体纯的碳酸盐的使用提供了具有整体保留构型（高达97％）的取代产物。
• Palladium-Catalyzed Asymmetric Benzylic Alkylation of Active Methylene Compounds with α-Naphthylbenzyl Carbonates and Pivalates
  作者：Sho Tabuchi、Koji Hirano、Masahiro Miura

  DOI：10.1002/anie.201602075

  日期：2016.6.6

  Pd/(R)‐H8‐BINAP‐catalyzed asymmetric benzylic alkylation of active methylene compounds has been developed. The reaction proceeds without the use of an external base, and the starting racemic diarylmethyl carbonates are converted into the optically active coupling products which contain the benzylic chiral stereocenter by a dynamic kinetic asymmetric transformation (DYKAT). Additionally, with suitable

  已开发出Pd /（R）-H 8 -BINAP催化的活性亚甲基化合物的不对称苄基烷基化反应。反应在不使用外部碱的情况下进行，并且起始外消旋碳酸二芳基甲基碳酸酯通过动态动力学不对称转化（DYKAT）被转化为包含苄基手性立体中心的旋光偶联产物。另外，对于合适的碳酸盐碱，相同的钯催化作用允许在相同的DYKAT工艺中采用相应的新戊酸酯。
• DMF as a dimethylamine equivalent in the palladium-catalyzed nucleophilic substitution of naphthylmethyl and allyl acetates
  作者：Martial Toffano、Jean-Yves Legros、Jean-Claude Fiaud

  DOI：10.1016/s0040-4039(96)02219-8

  日期：1997.1

  Naphthylmethyl acetates 1a and 2a were substituted by morpholine in DMPU in the presence of 2 mol% of [Pd(dba)(2) + 15 dppe] to give products 9-10 in 66-70% isolated yield. In DMF in the presence of benzylamine, N,N-dimethylnaphthylmethylamines 11-12 were produced in 78-85% isolated yield. Copyright (C) 1996 Elsevier Science Ltd
• Palladium-catalyzed nucleophilic substitution of napht hylmethyl and 1-naphthylethyl esters
  作者：Jean-Yves Legros、Jean-Claude Fiaud

  DOI：10.1016/s0040-4039(00)92227-5

  日期：1992.4

  Sodium dimethyl malonate reacted with naphthylmethyl and 1-naphthylethyl alcohol derivatives in DMF at 20-80-degrees-C, under palladium(0) / phosphine catalysis. to give the substitution products dimethyl naphthylmethyl- and 1-naphthylethylmalonates. respectively, in good (75-83%) yield.