(E)-dodec-2-enedioic acid dimethyl ester | 13038-20-5

• 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)-dodec-2-enedioic acid dimethyl ester
• 英文别名: 2-Dodecenedioic acid, dimethyl ester, (E)-；dimethyl (E)-dodec-2-enedioate
• CAS: 13038-20-5
• 化学式: C₁₄H₂₄O₄
• 分子量: 256.342
• InChiKey: XKZYDAGFYXSVFG-PKNBQFBNSA-N

物化性质

• 保留指数：
  1881.5

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (E)-dodec-2-enedioic acid dimethyl ester 在 氢氧化钾 作用下， 生成 反式-2-十二碳烯二酸
  参考文献：
  名称：

  Dolezal,S., Collection of Czechoslovak Chemical Communications, 1966, vol. 31, p. 3765 - 3774

  摘要：

  DOI：
• 作为产物：
  描述：

  10-烯酸甲酯 在 过氧化苯甲酰 作用下， 生成 (E)-dodec-2-enedioic acid dimethyl ester
  参考文献：
  名称：

  Dolezal,S., Collection of Czechoslovak Chemical Communications, 1966, vol. 31, p. 3765 - 3774

  摘要：

  DOI：

文献信息

• Nitro-Grela-type complexes containing iodides – robust and selective catalysts for olefin metathesis under challenging conditions
  作者：Andrzej Tracz、Mateusz Matczak、Katarzyna Urbaniak、Krzysztof Skowerski

  DOI：10.3762/bjoc.11.198

  日期：——

  Iodide-containing nitro-Grela-type catalysts have been synthesized and applied to ring closing metathesis (RCM) and cross metathesis (CM) reactions. These new catalysts have exhibited improved efficiency in the transformation of sterically, non-demanding alkenes. Additional steric hindrance in the vicinity of ruthenium related to the presence of iodides ensures enhanced catalyst stability. The benefits are most apparent under challenging conditions, such as very low reaction concentrations, protic solvents or with the occurrence of impurities.

  含碘的硝基-Grela型催化剂已合成并应用于闭环复分解反应（RCM）和交叉复分解反应（CM）。这些新催化剂在转化非空间位阻要求的烯烃方面表现出了提高的效率。由于碘化物存在导致的钌附近额外的空间位阻确保了催化剂稳定性的增强。在极具挑战性的条件下，例如非常低的反应浓度、质子溶剂或存在杂质时，这些优势最为明显。
• Exceptionally Stable and Efficient Solid Supported Hoveyda-Type Catalyst
  作者：Krzysztof Skowerski、Jakub Pastva、Stefan J. Czarnocki、Jana Janoscova

  DOI：10.1021/acs.oprd.5b00132

  日期：2015.7.17

  tagged Hoveyda-type catalyst bearing sterically enlarged N-heterocyclic carbene ligand was synthesized and supported on SBA-15. The obtained heterogeneous olefin metathesis catalyst forms unprecedentedly stable Ru-methylidenes and provides products of ring-closing and cross metathesis with turnover numbers (TONs) up to 35 000 and turnover frequencies (TOFs) up to 1590 min–1. The catalyst proved to be truly

  合成了具有空间扩大的N-杂环卡宾配体的铵标记的霍维达型催化剂，并将其负载在SBA-15上。所获得的非均相烯烃复分解催化剂形成了前所未有的稳定的Ru-亚甲基，并提供了闭环和交叉复分解的产物，其周转数（TON）高达35 000，周转频率（TOFs）高达1590 min –1。事实证明该催化剂是真正可回收的，并且在连续流模式下有效。
• Renewable Polyethers via GaBr ₃ ‐Catalyzed Reduction of Polyesters
  作者：Patrick‐Kurt Dannecker、Ursula Biermann、Marc von Czapiewski、Jürgen O. Metzger、Michael A. R. Meier

  DOI：10.1002/anie.201804368

  日期：2018.7.9

  Herein, a novel approach is reported for the synthesis of medium‐ and long‐chain aliphatic polyethers 2 based on the GaBr3‐catalysed reduction of polyesters 1 with TMDS as the reducing agent. Thus, various linear and branched aliphatic polyesters 1 were prepared and systematically investigated for this reduction strategy, demonstrating the applicability and versatility of this new polyether synthesis

  本文报道了一种新颖的方法，该方法基于以TMDS为还原剂的GaBr 3催化的聚酯1的还原反应，合成中链和长链脂族聚醚2。因此，制备了各种直链和支链脂族聚酯1并针对该还原策略进行了系统研究，证明了这种新的聚醚合成方案的适用性和多功能性。中期和长链链聚醚分别从各自的聚酯没有或有轻微的链降解获得，而短链聚酯，如聚-升-丙交酯1 I和聚[（[R）-3-羟基丁酸酯] 1焦耳，显示出主要的链降解。以这种方式，获得并研究了先前不可用和不常见的聚醚。
• Ruthenium–alkylidene catalysed cross-metathesis of fatty acid derivatives with acrylonitrile and methyl acrylate: a key step toward long-chain bifunctional and amino acid compounds
  作者：X. Miao、R. Malacea、C. Fischmeister、C. Bruneau、P. H. Dixneuf

  DOI：10.1039/c1gc15569e

  日期：——

  The ruthenium catalysed cross-metathesis of fatty-esters arising from plant oils with acrylonitrile is presented. The resulting linear nitrile ester products have potential as new intermediates for polyamides synthesis. A series of commercially available catalysts are able to promote the transformation of methyl 10-undecenoate 1, dimethyl octadec-9-en-1,18-dioate 5 and methyl ricinoleate 9 with acrylonitrile

  这 钌 催化交叉复分解 的 脂肪的--酯类 来自植物油的 丙烯腈被表达。结果线性腈 酯产品具有潜在的新中间体 聚酰胺纤维合成。一系列可商购的催化剂 能够促进变革 10-十一碳烯酸甲酯 1，octadec-9-en-1,18-diate的二甲基 5和甲基蓖麻油酸酯9与丙烯腈 和基于缓慢添加的协议 催化剂 允许交叉使用的TON高达1900（92％的收益）复分解 和 丙烯腈。这些交叉复分解 条件已应用于 丙烯酸甲酯 TON达到7600。
• An attempt to provide an environmentally friendly solvent selection guide for olefin metathesis
  作者：Krzysztof Skowerski、Jacek Białecki、Andrzej Tracz、Tomasz K. Olszewski

  DOI：10.1039/c3gc41943f

  日期：——

  A range of environmentally conservative solvents was evaluated for application in olefin metathesis. Different commercially available and most frequently applied ruthenium catalysts were employed. The data obtained can be used as a guide to facilitate replacement of environmentally detrimental chlorinated or aromatic solvents with greener reaction media in order to make applications of olefin metathesis in both industry and academia more environmentally benign and sustainable processes.

  一系列环境友好型溶剂被评估应用于烯烃复分解反应中。采用了不同市售且广泛应用的钌催化剂。所得数据可作为指南，促进以更绿色的反应介质替代对环境有害的氯化或芳香族溶剂，从而使烯烃复分解技术在工业和学术领域的应用更加环保、可持续。