(3E,5E)-2,5-dimethylhepta-3,5-dien-1-ol | 1263103-64-5

• 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: (3E,5E)-2,5-dimethylhepta-3,5-dien-1-ol
• CAS: 1263103-64-5
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: UAXYJEBXQZTRSB-PTFSRLPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  10.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (3E,5E)-2,5-dimethylhepta-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， 以87%的产率得到(3E,5E)-2,5-dimethylhepta-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
• 作为产物：
  描述：

  反式-2-甲基-2-丁烯醛 、 (3-Hydroxy-2-methylpropyl)triphenylphosphanium iodide 在 正丁基锂 作用下， 以 四氢呋喃 、 hexanes 为溶剂， 反应 0.5h， 以50%的产率得到(3E,5E)-2,5-dimethylhepta-3,5-dien-1-ol
  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

• Catalytic Asymmetric Vinylogous Prins Cyclization: A Highly Diastereo- and Enantioselective Entry to Tetrahydrofurans
  作者：Youwei Xie、Gui-Juan Cheng、Sunggi Lee、Philip S. J. Kaib、Walter Thiel、Benjamin List

  DOI：10.1021/jacs.6b09129

  日期：2016.11.9

  cyclization. This reaction constitutes an efficient approach for highly diastereo- and enantioselective synthesis of tetrahydrofurans (THFs) and is catalyzed by a confined chiral imidodiphosphoric acid (IDP). Aromatic and heteroaromatic aldehydes react with various 3,5-dien-1-ols to afford 2,3-disubstituted THFs in excellent selectivity (d.r. > 20:1, e.r. up to 99:1). Aliphatic aldehydes react with similarly

  我们描述了第一个催化不对称乙烯基 Prins 环化的设计和开发。该反应构成了四氢呋喃 (THF) 的高度非对映选择性和对映选择性合成的有效方法，并由受限的手性亚胺二磷酸 (IDP) 催化。芳香族和杂芳香族醛与各种 3,5-二烯-1-醇反应，以优异的选择性（dr > 20:1，er 高达 99:1）得到 2,3-二取代的 THF。当使用高酸性的亚氨基二磷亚胺酯 (IDPi) 催化剂时，脂肪醛的反应结果也同样出色。对于外消旋二烯醇，反应通过动力学拆分进行。DFT 计算提出了异常高立体选择性的解释。
• 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.