(E)-dimethyl 2,5-dimethyl-2-hexenedioate | 67237-56-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-dimethyl 2,5-dimethyl-2-hexenedioate
• 英文别名: (E)-dimethyl 2,5-dimethylhex-2-enedioate；dimethyl (E)-2,5-dimethyl-2-hexenedioate；(E)-2,5-Di(methoxycarbonyl)-hex-2-en；Dimethyl 2,5-dimethylhex-2-enedioate；dimethyl (E)-2,5-dimethylhex-2-enedioate
• CAS: 67237-56-3
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: ZXXDDSPXEBOXDR-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E),(E)-2,5-Di(methoxycarbonyl)-hexa-2,4-dien 在 sodium methylate 、 锌 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 (E)-dimethyl 2,5-dimethyl-2-hexenedioate
  参考文献：
  名称：

  Oehme, G., Journal fur praktische Chemie (Leipzig 1954), 1984, vol. 326, # 5, p. 779 - 790

  摘要：

  DOI：

文献信息

• N-Heterocyclic Carbene Catalyzed Umpolung of Michael Acceptors for Intermolecular Reactions
  作者：Akkattu T. Biju、Mohan Padmanaban、Nathalie E. Wurz、Frank Glorius

  DOI：10.1002/anie.201103555

  日期：2011.8.29

  leahciM! The N‐heterocyclic carbene catalyzed umpolung of Michael acceptors proceeds through the formation of a deoxy‐Breslow intermediate (see scheme; EWG=electron‐withdrawing group). This nucleophilic species can react with other Michael acceptors in an intermolecular fashion, thereby resulting in the formation of homo‐ or heterodimeric olefins. This “Michael umpolung” should become a valuable method

  漏气！N杂环卡宾催化的Michael受体的化合物通过形成脱氧Breslow中间体进行（参见方案； EWG =吸电子基团）。这种亲核物质可以分子间方式与其他迈克尔受体反应，从而导致形成同二聚或异二聚烯烃。这种“ Michael umpolung”应该成为形成致密官能化烯烃的一种有价值的方法。
• [EN] PROCESS FOR THE DIMERIZATION OF ACTIVATED OLEFINS<br/>[FR] PROCÉDÉ DE DIMÉRISATION D'OLÉFINES ACTIVÉES
  申请人：BASF SE

  公开号：WO2015177141A1

  公开（公告）日：2015-11-26

  The present invention relates to a process for the preparation of compounds or a mixture of compounds of the general formulae I.a or I.b wherein R1 is selected from C1-C12-alkyl, C3-C6-cycloalkyl, -C(=O)OR2, -PO(OR2a)2, aryl and hetaryl, R2, R2a are independently of each other selected from the group consisting of hydrogen,C1-C12-alkyl, C1-C12-alkenyl, where the last two radicals mentioned are unsubstituted, partly or completely halogenated or substituted by 1, 2, 3 or 4 radicals selected from the group consisting of C1-C6-alkoxy and CN, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, aryl and aryl-C1-C4 -alkyl, where the last four radicals mentioned are unsubstituted or substituted by 1, 2, 3 or 4 radicals selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, -CN, and halogen, which comprises dimerizing olefin compound of the general formula II, in the presence of at least one N-heterocyclic carbene catalyst.

  本发明涉及一种制备化合物或通式I.a或I.b混合物的方法，其中R1选自C1-C12烷基，C3-C6环烷基，-C（=O）OR2，-PO（OR2a）2，芳基和杂芳基，R2，R2a分别选自氢，C1-C12烷基，C1-C12烯基，其中上述最后两个基团未取代，部分或完全卤代或由选自C1-C6烷氧基和CN，C3-C6环烷基，C3-C6环烷基-C1-C4烷基，芳基和芳基-C1-C4-烷基的1,2,3或4个基团取代，其中上述最后四个基团未取代或由选自C1-C6烷基，C1-C6卤代烷基，C1-C6烷氧基，C1-C6卤代烷氧基，-CN和卤素的1,2,3或4个基团取代，包括在至少一种N-杂环卡宾催化剂的存在下，使通式II的烯烃化合物发生二聚化反应的方法。
• Aroma chemicals
  申请人：BASF SE

  公开号：US10066188B2

  公开（公告）日：2018-09-04

  The present invention relates to the use of diesters of 2,5-dimethyl-2-hexenedioic acid, 2,5-dimethyl-3-hexenedioic acid and 2,5-dimethyladipic acid or a mixture thereof as a fragrance or as flavor, to a method for imparting or modifying a scent or a flavor to a composition by including said compounds into such composition, to a fragrance containing composition and/or a fragrance material containing said compounds and to a process for preparing diesters of 2,5-dimethyladipic acid.

  本发明涉及 2,5-二甲基-2-己二酸、2,5-二甲基-3-己二酸和 2,5-二甲基己二酸的二酯或其混合物作为香料或香精的用途，涉及通过在组合物中加入上述化合物来赋予或改变组合物香味或香精的方法，涉及含有上述化合物的含香组合物和/或含香材料，还涉及制备 2,5-二甲基己二酸二酯的工艺。
• N -Heterocyclic carbene catalyzed tail-to-tail oligomerization of N , N -dimethylacrylamide (DMAA) and the search for the Stetter reaction of DMAA with benzaldehyde
  作者：Oue-artorn Rajachan、Mathias Paul、Veera Reddy Yatham、Jörg-M. Neudörfl、Kwanjai Kanokmedhakul、Somdej Kanokmedhakul、Albrecht Berkessel

  DOI：10.1016/j.tetlet.2015.09.104

  日期：2015.11

  The tail-to-tail oligomerization of N,N-dimethylacrylamide catalyzed by N-heterocyclic carbenes (NHCs) was investigated, giving the dimerization and trimerization products in a moderate combined yield. Reaction intermediates involved in the new oligomerization have been observed by NMR and ESI-MS. We showed the first NHC-catalyzed cross coupling of methyl methacrylate and N,N-dimethylaciylamide, and the reaction of benzaldehyde/benzoin with N,N-dimethylacrylamide. (C) 2015 Elsevier Ltd. All rights reserved.
• Organocatalytic Tail-to-Tail Dimerization of Olefin: Umpolung of Methyl Methacrylate Mediated by N-Heterocyclic Carbene
  作者：Shin-ichi Matsuoka、Yoshiya Ota、Atsushi Washio、Akiho Katada、Kenji Ichioka、Koji Takagi、Masato Suzuki

  DOI：10.1021/ol201380m

  日期：2011.7.15

  Highly selective tail-to-tall dimerization of methyl methacrylate has been realized by an N-heterocyclic carbene catalyst, giving dimethyl 2,5-dimethyl-2-hexenedioate with an E/Z ratio of 95:5 in 86% isolated yield. The umpolung mechanism Is proposed on the basis of Interception of the intermediates using ESI-MS analyses and deuterium-labeling experiments.