4-trans-styryl-hepta-1,6-dien-4-ol | 92581-12-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: 4-trans-styryl-hepta-1,6-dien-4-ol
• 英文别名: Styryldiallylcarbinol；4-[(E)-2-phenylethenyl]hepta-1,6-dien-4-ol
• CAS: 92581-12-9
• 化学式: C₁₅H₁₈O
• 分子量: 214.307
• InChiKey: LNQTWWDXPHHJHS-JLHYYAGUSA-N

物化性质

• 沸点：
  117-118 °C(Press: 0.9 Torr)
• 密度：
  0.986±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  Methyl cinnamate 、 3-溴丙烯 在 二氯二茂钛 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到4-trans-styryl-hepta-1,6-dien-4-ol
  参考文献：
  名称：

  通过钛茂金属催化的烯丙基卤化物活化生成烯丙基格氏试剂

  摘要：

  本文描述了通过烯丙基卤的催化活化产生烯丙基格氏试剂的方案。随后的亲核加成羰基衍生物提供了所需的均烯丙基醇，产率极高（84-99％）。有证据表明，二茂钛二氯化物催化烯丙基格氏试剂的形成，该烯丙基格利雅试剂仅与羰基亲电试剂反应，这完全不存在Würtz偶联现象。该方法在高反应性有机金属试剂的产生中将具有广泛的适用性。

  DOI：

  10.1016/j.tetlet.2010.02.144

文献信息

• Organometallic-type reactions in aqueous media mediated by indium. Allylation of acyloyl-imidazoles and pyrazoles. Regioselective synthesis of β,γ-unsaturated ketones
  作者：Vernal J. Bryan、Tak-Hang Chan

  DOI：10.1016/s0040-4039(97)01512-8

  日期：1997.9

  Indium mediated coupling of allylic bromide with acyloyl-imidazoles or pyrazoles in aqueous media gives the corresponding tertiary alcohols or ketones in good yield. The reaction provides a facile regioselective synthesis of β,γ-unsaturated ketones and its usefulness is demonstrated by the synthesis of the monoterpene artemesia ketone.

  在水性介质中，铟介导的烯丙基溴与酰基酰咪唑或吡唑的偶合以良好的收率得到相应的叔醇或酮。该反应提供了β，γ-不饱和酮的容易的区域选择性合成，并且其有效性由单萜蒿蒿酮的合成证明。
• Regio- and diastereoselective conjugate addition of Grignard reagents to aryl substituted α,β-unsaturated carbonyl compounds derived from Oppolzer's sultam
  作者：Xiufang Cao、Fang Liu、Wenchang Lu、Gang Chen、Guang-Ao Yu、Sheng Hua Liu

  DOI：10.1016/j.tet.2008.04.048

  日期：2008.6

  Asymmetric conjugate addition of Grignard reagents to aryl substituted α,β-unsaturated carbonyl compounds (1) has been achieved with great regioselectivity (>20:1) and good to excellent diastereoselectivity (de up to 98%). The nucleophilicity and stereospecific blockade of the Grignard reagents play a key role in controlling the regioselectivities and diastereoselectivities of the conjugate addition

  已经实现了格氏试剂向芳基取代的α，β-不饱和羰基化合物（1）的不对称共轭加成，具有很高的区域选择性（> 20：1）和良好的至优异的非对映选择性（高达98％）。格氏试剂的亲核性和立体特异性阻断在控制缀合物加成反应的区域选择性和非对映选择性中起关键作用。
• Tellurium-Zinc exchange between organotelluronium salts and diethylzinc—reaction of the in situ generated mixed diorganozinc with carbonyl compounds
  作者：Wen-Hua Huang、Yao-Zeng Huang、Li-Xin Dai

  DOI：10.1016/s0040-4039(98)01443-9

  日期：1998.9

  Organotelluronium salts undergo a smooth tellurium-zinc exchange reaction with diethylzinc. The in situ generated mixed diorganozinc reagents reacted with carbonyl compounds to give secondary or tertiary alcohols in good to excellent yields, (C) 1998 Elsevier Science Ltd. All rights reserved.
• 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.