(3E,5E)-hepta-3,5-dien-1-yl α-bromoacetate | 1263103-96-3

• 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: (3E,5E)-hepta-3,5-dien-1-yl α-bromoacetate
• 英文别名: [(3E,5E)-hepta-3,5-dienyl] 2-bromoacetate
• CAS: 1263103-96-3
• 化学式: C₉H₁₃BrO₂
• 分子量: 233.105
• InChiKey: KKVYYFYRQSSTDK-MQQKCMAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  乙醛酸乙酯 、 (3E,5E)-hepta-3,5-dien-1-yl α-bromoacetate 在 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 ethyl (4aSR,7RS,8SR,8aSR)-7-methyl-1-oxo-3,4,4a,7,8,8a-hexahydro-1H-isochromene-8-carboxylate 、 ethyl (4aSR,7RS,8RS,8aRS)-7-methyl-1-oxo-3,4,4a,7,8,8a-hexahydro-1H-isochromene-8-carboxylate 、 ethyl (4aSR,7RS,8RS,8aSR)-7-methyl-1-oxo-3,4,4a,7,8,8a-hexahydro-1H-isochromene-8-carboxylate 、 ethyl (4aSR,7RS,8SR,8aRS)-7-methyl-1-oxo-3,4,4a,7,8,8a-hexahydro-1H-isochromene-8-carboxylate
  参考文献：
  名称：

  Tandem Wittig–intramolecular Diels–Alder cycloaddition of ester-tethered 1,3,9-decatrienes under microwave heating

  摘要：

  Intramolecular Diels Alder (IMDA) cycloaddition of the ester-tethered 1,3,9,-decatrienes possessing a carbonyl substituent at C10 has been investigated under controlled microwave heating (MeCN, 180 degrees C) to afford a variety of 3,4,4a,7,8,8a-hexahydroisochromen-1-ones in 53-89% yields and in 64:36-79:21 ratios for the cis and trans isomers. Under the same microwave heating conditions, a tandem Wittig-IMDA cycloaddition, starting from the alpha-bromoacetates of 3,5-hexadien-1-ols and glyoxalate/phenylglyoxal hydrates in the presence of PPh3 and 2,6-lutidine, has been demonstrated, furnishing 3,4,4a,7,8,8a-hexahydroisochromen-1-one adducts in 73-91% yields in favor of the cis isomers. During this tandem process, three consecutive carbon carbon bonds in the end products were efficiently formed with the aid of microwave irradiation within short reaction times. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.088
• 作为产物：
  描述：

  (5E)-hepta-3,5-dien-1-ol 、 溴乙酸 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， 生成 (3Z,5E)-hepta-3,5-dien-1-yl α-bromoacetate 、 (3E,5E)-hepta-3,5-dien-1-yl α-bromoacetate
  参考文献：
  名称：

  Tandem Wittig–intramolecular Diels–Alder cycloaddition of ester-tethered 1,3,9-decatrienes under microwave heating

  摘要：

  Intramolecular Diels Alder (IMDA) cycloaddition of the ester-tethered 1,3,9,-decatrienes possessing a carbonyl substituent at C10 has been investigated under controlled microwave heating (MeCN, 180 degrees C) to afford a variety of 3,4,4a,7,8,8a-hexahydroisochromen-1-ones in 53-89% yields and in 64:36-79:21 ratios for the cis and trans isomers. Under the same microwave heating conditions, a tandem Wittig-IMDA cycloaddition, starting from the alpha-bromoacetates of 3,5-hexadien-1-ols and glyoxalate/phenylglyoxal hydrates in the presence of PPh3 and 2,6-lutidine, has been demonstrated, furnishing 3,4,4a,7,8,8a-hexahydroisochromen-1-one adducts in 73-91% yields in favor of the cis isomers. During this tandem process, three consecutive carbon carbon bonds in the end products were efficiently formed with the aid of microwave irradiation within short reaction times. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.088

文献信息

• Tandem Wittig–intramolecular Diels–Alder cycloaddition of ester-tethered 1,3,9-decatrienes under microwave heating
  作者：Jinlong Wu、Xiuqing Jiang、Jingjing Xu、Wei-Min Dai

  DOI：10.1016/j.tet.2010.10.088

  日期：2011.1

  Intramolecular Diels Alder (IMDA) cycloaddition of the ester-tethered 1,3,9,-decatrienes possessing a carbonyl substituent at C10 has been investigated under controlled microwave heating (MeCN, 180 degrees C) to afford a variety of 3,4,4a,7,8,8a-hexahydroisochromen-1-ones in 53-89% yields and in 64:36-79:21 ratios for the cis and trans isomers. Under the same microwave heating conditions, a tandem Wittig-IMDA cycloaddition, starting from the alpha-bromoacetates of 3,5-hexadien-1-ols and glyoxalate/phenylglyoxal hydrates in the presence of PPh3 and 2,6-lutidine, has been demonstrated, furnishing 3,4,4a,7,8,8a-hexahydroisochromen-1-one adducts in 73-91% yields in favor of the cis isomers. During this tandem process, three consecutive carbon carbon bonds in the end products were efficiently formed with the aid of microwave irradiation within short reaction times. (C) 2010 Elsevier Ltd. All rights reserved.