4-ethyl-1,6-heptadien-4-ol | 52939-62-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-ethyl-1,6-heptadien-4-ol
• 英文别名: 4-ethyl-hepta-1,6-dien-4-ol；4-Aethyl-hepta-1,6-dien-4-ol；Aethyl-diallyl-carbinol；4-ethylhepta-1,6-dien-4-ol
• CAS: 52939-62-5
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: ZNYOYPXOCNWHCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-ethyl-1,6-heptadien-4-ol 在 硫酸 、 双氧水 、 臭氧 、 溶剂黄146 作用下， 生成 3-羟基-3-乙基戊二酸
  参考文献：
  名称：

  3-Alkyl-3-hydroxyglutaric Acids: A New Class of Hypocholesterolemic HMG CoA Reductase Inhibitors. 1

  摘要：

  Derivatives of 3-hydroxy-3-methylglutaric acid (HMG), a portion of the substrate for HMG CoA reductase, were prepared and tested for their inhibitory action against rat liver HMG CoA reductase and for their hypocholesterolemic activity. Structure-dependent competitive inhibition was observed. Optimal structures had a free dicarboxylic acid with an alkyl group of 13-16 carbons at position 3. 3-n-Pentadecyl-3-hydroxyglutaric acid (3j) (IC50 = 50 microM) reduced serum cholesterol in the Triton-treated rat and HMG CoA reductase activity in the 20,25-diazacholesterol-treated rat.

  DOI：

  10.1021/jm50001a011
• 作为产物：
  描述：

  丙酸乙酯 、 3-溴丙烯 在 氢化镝(DyH3) 、 mercury dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以84%的产率得到4-ethyl-1,6-heptadien-4-ol
  参考文献：
  名称：

  在氯化汞存在下由金属镝促进的酯的烯丙基化

  摘要：

  摘要 在氯化汞存在下，酯与烯丙基溴和金属镝在无水 THF 中的反应以良好的收率得到二烯丙基烷基甲醇。当以γ-丁内酯为底物时，相应的产物为4-allyl-6-heptene-1, 4-diol。

  DOI：

  10.1081/scc-120006467

文献信息

• Metal zinc-promoted gem -bisallylation of acid chlorides with allyl chlorides in the presence of chlorotrimethylsilane
  作者：Yoshio Ishino、Masatoshi Mihara、Manabu Kageyama

  DOI：10.1016/s0040-4039(02)01437-5

  日期：2002.9

  Treatment of acid chlorides (2) with allyl chlorides (1) in the presence of zinc dust and a catalytic amount of chlorotrimethylsilane (TMSCl) in THF brought about highly facile and effective coupling to give the corresponding gem-bisallylation products. 4-hydroxy-penta-1,6-dienes (3), in good to excellent yields. These reactions are assumed to proceed through allylzinc intermediates generated in situ. (C) 2002 Elsevier Science Ltd. All rights reserved.
• An efficient of Grignard-type procedure for the preparation of gem-diallylated compound
  作者：Kao-Hsien Shen、Chun-Wei Kuo、Ching-Fa Yao

  DOI：10.1016/j.tetlet.2007.07.008

  日期：2007.9

  An efficient and a new procedure for the conversion of various carboxylic acid derivatives into the corresponding gemdiallylated compound under mild reaction condition has been developed. The triallyaluminum mediated Grignard-type addition of carboxylic acid derivative was utilized as a key operation to affect the transformation. The procedure is operationally simple, giving good to excellent product yields for a broad range of substrates. The chemoselectivity and regioselectivity of triallylaluminum were also demonstrated. (C) 2007 Elsevier Ltd. All rights reserved.
• Henze; Allen; Leslie, Journal of Organic Chemistry, 1942, vol. 7, p. 333
  作者：Henze、Allen、Leslie

  DOI：——

  日期：——
• γ-Substituted Organoalkali Compounds; Preparation and Synthetic Applications
  作者：José Barluenga、Josefa Florez、Miguel Yus

  DOI：10.1055/s-1983-30342

  日期：——
• Solvent- and catalyst-free gem-bisallylation of carboxylic acid derivatives with allylzinc bromide
  作者：Yu-Juan Wei、Heng Ren、Jin-Xian Wang

  DOI：10.1016/j.tetlet.2008.07.097

  日期：2008.9

  A rapid and efficient procedure for the solvent-free synthesis of gem-bisallylation products has been achieved by allylzinc bromide with carboxylic acid derivatives in the absence of any catalysts at room temperature. (C) 2008 Elsevier Ltd. All rights reserved.