(2E,4E)-4-methyl-5-phenypenta-2,4-dien-1-yl α-bromoacetate

• 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: (2E,4E)-4-methyl-5-phenypenta-2,4-dien-1-yl α-bromoacetate
• 英文别名: [(2E,4E)-4-methyl-5-phenylpenta-2,4-dienyl] 2-bromoacetate
• 化学式: C₁₄H₁₅BrO₂
• 分子量: 295.176
• InChiKey: ALAIPSPNAVWBAY-VTNGQZISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 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)-4-methyl-5-phenypenta-2,4-dien-1-yl α-bromoacetate 、 乙醛酸乙酯水合物 在 2,6-二甲基吡啶 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 (3aR,4R,5R,7aS)-6-Methyl-3-oxo-5-phenyl-1,3,3a,4,5,7a-hexahydro-isobenzofuran-4-carboxylic acid ethyl ester 、 、 ethyl (3aS,4R,5S,7aS)-6-methyl-3-oxo-5-phenyl-3a,4,5,7a-tetrahydro-1H-2-benzofuran-4-carboxylate 、
  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：

  溴乙酸 、 (2E,4E)-4-methyl-5-phenylpenta-2,4-dien-1-ol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以86%的产率得到(2E,4E)-4-methyl-5-phenypenta-2,4-dien-1-yl α-bromoacetate
  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

文献信息

• 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.