dimethyl 2-(benzyloxy)succinate | 134356-95-9

• 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: dimethyl 2-(benzyloxy)succinate
• 英文别名: dimethylbutoxysuccinate；R,S-2-O-benzylmalate；Dimethyl 2-phenylmethoxybutanedioate
• CAS: 134356-95-9；82130-73-2；116233-49-9
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: OJIKXLSNRLSSKS-UHFFFAOYSA-N

物化性质

• 沸点：
  349.3±27.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  dimethyl 2-(benzyloxy)succinate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.17h， 生成 2-(苄氧基)-1,4-丁二醇
  参考文献：
  名称：

  Investigating the role of the hydroxyl groups of substrate erythrose 4-phosphate in the reaction catalysed by the first enzyme of the shikimate pathway

  摘要：

  3-Deoxy-D-arabino-heptulosonate 7-phosphate (DAH7P) synthase catalyses the first step of the shikimate pathway, which is responsible for the biosynthesis of aromatic amino acids in microorganisms and plants. This enzyme catalyses an aldol reaction between phosphoenolpyruvate and D-erythrose 4-phosphate to generate DAH7P. Both 2-deoxyerythrose 4-phosphate and 3-deoxyerythrose 4-phosphate were synthesised and tested as alternative substrates for the enzyme. Both compounds were found to be substrates for the DAH7P synthases from Escherichia coli, Pyrococcus furiosus and Mycobacterium tuberculosis, consistent with an acyclic mechanism for the enzyme for which neither C2 nor C3 hydroxyl groups are required for catalysis. The enzymes all showed greater tolerance for the loss of the C2 hydroxyl group than the C3 hydroxyl group. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.017
• 作为产物：
  描述：

  DL-苹果酸二甲酯 、 2,2,2-三氯乙酰胺苄酯 在 三氟甲磺酸 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 以66%的产率得到dimethyl 2-(benzyloxy)succinate
  参考文献：
  名称：

  通过 InBr3/TMDS 环化二羧酸合成 3-取代四氢呋喃和 4-取代四氢吡喃衍生物

  摘要：

  据报道，使用 InBr3/TMDS 系统对二酸化合物进行有效还原，然后环化。该系统允许形成在 3 位或 4 位取代的五元和六元环醚。

  DOI：

  10.1002/ejoc.201200727

文献信息

• Santaniello, Enzo; Ferraboschi, Patrizia; Grisenti, Paride, Journal of the Chemical Society. Perkin transactions I, 1991, # 3, p. 601 - 605
  作者：Santaniello, Enzo、Ferraboschi, Patrizia、Grisenti, Paride、Aragozzini, Fabrizio、Maconi, Elisabetta

  DOI：——

  日期：——
• Investigating the role of the hydroxyl groups of substrate erythrose 4-phosphate in the reaction catalysed by the first enzyme of the shikimate pathway
  作者：David Tran、Amy L. Pietersma、Linley R. Schofield、Matthias Rost、Geoffrey B. Jameson、Emily J. Parker

  DOI：10.1016/j.bmcl.2011.09.017

  日期：2011.11

  3-Deoxy-D-arabino-heptulosonate 7-phosphate (DAH7P) synthase catalyses the first step of the shikimate pathway, which is responsible for the biosynthesis of aromatic amino acids in microorganisms and plants. This enzyme catalyses an aldol reaction between phosphoenolpyruvate and D-erythrose 4-phosphate to generate DAH7P. Both 2-deoxyerythrose 4-phosphate and 3-deoxyerythrose 4-phosphate were synthesised and tested as alternative substrates for the enzyme. Both compounds were found to be substrates for the DAH7P synthases from Escherichia coli, Pyrococcus furiosus and Mycobacterium tuberculosis, consistent with an acyclic mechanism for the enzyme for which neither C2 nor C3 hydroxyl groups are required for catalysis. The enzymes all showed greater tolerance for the loss of the C2 hydroxyl group than the C3 hydroxyl group. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of 3-Substituted Tetrahydrofuran and 4-Substituted Tetrahydropyran Derivatives by Cyclization of Dicarboxylic Acids with InBr3/TMDS
  作者：Leyla Pehlivan、Estelle Métay、Dominique Delbrayelle、Gérard Mignani、Marc Lemaire

  DOI：10.1002/ejoc.201200727

  日期：2012.9

  An efficient reduction followed by cyclization of diacid compounds with the InBr3/TMDS system is reported. This system allows the formation of five- and six-membered ring ethers substituted in the 3- or 4-position.

  据报道，使用 InBr3/TMDS 系统对二酸化合物进行有效还原，然后环化。该系统允许形成在 3 位或 4 位取代的五元和六元环醚。