(2E,4E)-hexa-2,4-dien-1-yl α-bromoacetate | 909731-01-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2E,4E)-hexa-2,4-dien-1-yl α-bromoacetate
• 英文别名: [(2E,4E)-hexa-2,4-dienyl] 2-bromoacetate
• CAS: 909731-01-7
• 化学式: C₈H₁₁BrO₂
• 分子量: 219.078
• InChiKey: FWVILEPMBIPKMF-MQQKCMAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,4E)-hexa-2,4-dien-1-yl α-bromoacetate 在 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 12.5h， 生成 (2'E,4'E)-hexa-2',4'-dien-1'-yl (2E)-4-phenyl-4-oxo-2-butenoate
  参考文献：
  名称：

  Microwave-assisted tandem Wittig–intramolecular Diels–Alder cycloaddition. Product distribution and stereochemical assignment

  摘要：

  The IMDA cycloadditions of 10 different ester-tethered 1,3,8-nonatrienes have been examined under controlled microwave heating (MeCN, 180 degrees C, 30 min), giving 90-99% yields, and the stereochemical outcome of the exo and endo adducts established together with X-ray crystal structural analysis. A microwave-assisted tandem Wittig-IMDA cycloaddition protocol has been established for a modular synthesis of the bicyclic lactones starting from alpha-bromoacetates of 2,4-pentadien-1-ols and alpha-oxo carbonyl compounds in the presence of PPh3 and 2,6-lutidine (MeCN, 180 degrees C, 30 min). The overall yields of the tandem reactions are 68-80% and the stereoselectivity of the major adducts formed from E-substituted 1,3,8-nonatriene is the same as that observed for the purified 1,3,8-nonatrienes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.039
• 作为产物：
  描述：

  (2E,4E)-2,4-己二烯-1-醇 、 溴乙酰溴 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 (2E,4E)-hexa-2,4-dien-1-yl α-bromoacetate
  参考文献：
  名称：

  水溶性手性钌（II）苯基恶唑啉配合物：分子内环丙烷化反应的可重用和高对映选择性催化剂。

  摘要：

  通过在水/醚中使用水溶性钌（II）/羟甲基（苯基）恶唑啉催化剂，已经实现了各种反式烯丙基重氮乙酸酯和烯基重氮酮的分子内环丙烷化，具有高达98％ee的优异对映选择性，并以定量产率获得双相介质。催化剂可以重复使用至少五次。

  DOI：

  10.1002/adsc.201200508

文献信息

• Water-Soluble Chiral Ruthenium(II) Phenyloxazoline Complex: Reusable and Highly Enantioselective Catalyst for Intramolecular Cyclopropanation Reactions
  作者：Abdel-Moneim Abu-Elfotoh、Diem Phuong Thi Nguyen、Soda Chanthamath、Kesiny Phomkeona、Kazutaka Shibatomi、Seiji Iwasa

  DOI：10.1002/adsc.201200508

  日期：2012.12.14

  The intramolecular cyclopropanation of various trans-allylic diazoacetates and alkenyl diazoketones has been achieved with excellent enantioselectivities of up to 98% ee and in quantitative yields by using a water-soluble ruthenium(II)/hydroxymethyl(phenyl)oxazoline catalyst in a water/ether biphasic medium. The catalyst could be reused at least five times.

  通过在水/醚中使用水溶性钌（II）/羟甲基（苯基）恶唑啉催化剂，已经实现了各种反式烯丙基重氮乙酸酯和烯基重氮酮的分子内环丙烷化，具有高达98％ee的优异对映选择性，并以定量产率获得双相介质。催化剂可以重复使用至少五次。
• Microwave-assisted tandem Wittig–intramolecular Diels–Alder cycloaddition. Product distribution and stereochemical assignment
  作者：Jinlong Wu、Lijie Sun、Wei-Min Dai

  DOI：10.1016/j.tet.2006.06.039

  日期：2006.8

  The IMDA cycloadditions of 10 different ester-tethered 1,3,8-nonatrienes have been examined under controlled microwave heating (MeCN, 180 degrees C, 30 min), giving 90-99% yields, and the stereochemical outcome of the exo and endo adducts established together with X-ray crystal structural analysis. A microwave-assisted tandem Wittig-IMDA cycloaddition protocol has been established for a modular synthesis of the bicyclic lactones starting from alpha-bromoacetates of 2,4-pentadien-1-ols and alpha-oxo carbonyl compounds in the presence of PPh3 and 2,6-lutidine (MeCN, 180 degrees C, 30 min). The overall yields of the tandem reactions are 68-80% and the stereoselectivity of the major adducts formed from E-substituted 1,3,8-nonatriene is the same as that observed for the purified 1,3,8-nonatrienes. (c) 2006 Elsevier Ltd. All rights reserved.
• Visible-Light-Induced Photocatalytic Aerobic Oxidation/Povarov Cyclization Reaction: Synthesis of Substituted Quinoline-Fused Lactones
  作者：Wuheng Dong、Bei Hu、Xiaoshuang Gao、Yuyuan Li、Xiaomin Xie、Zhaoguo Zhang

  DOI：10.1021/acs.joc.6b01253

  日期：2016.10.7

  A one-step construction of quinoline-fused lactones was achieved by visible-light-induced photocatalytic aerobic oxidation/Povarov cyclization reaction. This method provides a new access to the synthesis of important fused heterocycles under mild reaction conditions.

  通过可见光诱导的光催化好氧氧化/ Povarov环化反应实现了喹啉融合内酯的一步制备。该方法为在温和的反应条件下合成重要的稠合杂环提供了新途径。