1,3-diphenyl-hexa-1,5-dien-3-ol | 21573-76-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 1,3-diphenyl-hexa-1,5-dien-3-ol
• 英文别名: 1,3-diphenylhexa-1,5-dien-3-ol
• CAS: 21573-76-2
• 化学式: C₁₈H₁₈O
• 分子量: 250.34
• InChiKey: DXVACVIQEVLTDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  170-170.5 °C
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  烯丙基三丁基锡 、 苯亚甲基苯乙酮 在 copper(l) iodide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以95%的产率得到1,3-diphenyl-hexa-1,5-dien-3-ol
  参考文献：
  名称：

  Facile chemoselective carbonyl allylation of chalcones with allyltributylstannane catalyzed by CuI

  摘要：

  Chemoselective allylation of carbonyl functionality of chalcones with allyltributylstannane was accomplished in the presence of CuI as catalyst. This reaction works well in DMF at 70 degrees C with exclusive formation of 1,2-addition product. Interesting feature of this reaction is that no conjugate addition product was produced. Various types of chalcones undergo carbonyl allylation in excellent yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.037

文献信息

• The reaction of allyl iodide with ketones in the presence of cerium amalgam. An efficient method for the preparation of homoallylic alcohols
  作者：Tsuneo Imamoto、Yasuo Hatanaka、Yoshinori Tawarayama、Masataka Yokoyama

  DOI：10.1016/s0040-4039(01)92399-8

  日期：1981.1

  Allyl iodide reacts in situ with cerium amalgam to generate allyl cerium iodide, which in turn reacts with ketones to yield homoallylic alcohols in good yields.

  烯丙基碘化物与铈汞齐原位反应生成烯丙基碘化铈，后者又与酮反应生成高收率的均烯丙基醇。
• Highly Regioselective Allylation of α-Enones and Epoxides with Lithium Tetraallyllanthanoid Ate Complex
  作者：Shin-ichi Fukuzawa、Shizuyoshi Sakai

  DOI：10.1246/bcsj.65.3308

  日期：1992.12

  be involved in this carbonyl allylation reaction with 1. Allylative ring opening of styrene oxide with 1 occurs at the more subsituted carbon (α-attack) in higher selectivity (α : β = 85 : 15) than with allyllithium and allylmagnesium bromide in diethyl ether. The complex 1 reacts with 3,4-epoxy-1-butene (35) in diethyl ether predominantly at the most substituted carbon of the oxirane to give 3-hydroxymethyl-1

  由四烯丙基锡、三氯化镧和丁基锂在四氢呋喃 (THF) 中很容易原位制备的四烯丙基镧系化合物 (1) 与 α-烯酮 (3-11) 以高度的 1,2-区域选择性 (1) 顺利反应,2 : 1,4 = >99 : 1) 以良好到极好的产率得到 1,5-二烯-3-醇。以 4,4-(乙二氧基)-2,6-二甲基-2,5-环己二烯酮 (29) 作为探针的机理研究表明，单电子转移 (SET) 可能参与了与 1. 烯丙基化环的羰基烯丙基化反应与烯丙基锂和烯丙基溴化镁在乙醚中相比，氧化苯乙烯与 1 的开环发生在更多取代的碳（α-攻击）上，选择性更高（α : β = 85 : 15）。络合物 1 与 3 反应，
• Mechanochemistry‐Amended Barbier Reaction as an Expedient Alternative to Grignard Synthesis**
  作者：Jagadeesh Varma Nallaparaju、Tatsiana Nikonovich、Tatsiana Jarg、Danylo Merzhyievskyi、Riina Aav、Dzmitry G. Kananovich

  DOI：10.1002/anie.202305775

  日期：2023.9.25

  Use of mechanochemistry enabled the rapid in situ generation of Grignard reagents, thereby overcoming the longstanding limitations of the Magnesium-mediated Barbier reaction in solution.

  机械化学的使用使得格氏试剂能够快速原位生成，从而克服了溶液中镁介导的巴比尔反应的长期限制。
• 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.
• Organoboron compounds
  作者：G. S. Ter-Sarkisyan、N. A. Nikolaeva、B. M. Mikhailov

  DOI：10.1007/bf00903385

  日期：1968.11