3-methyl-1-phenylhexa-4,5-dien-3-ol | 84920-35-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methyl-1-phenylhexa-4,5-dien-3-ol
• 英文别名: 4-methyl-6-phenyl-1,2-hexadien-4-ol
• CAS: 84920-35-4
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: ZZQJNLMOQINZFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  苄基丙酮 、 prop-2-yn-1-yl 4-methylbenzoate 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以36%的产率得到3-methyl-1-phenylhex-5-yn-3-ol
  参考文献：
  名称：

  Toluates: unexpectedly versatile reagents

  摘要：

  The mechanism of the monoelectronic reduction of aromatic esters has been investigated. The unexpected synthetic utility of the toluate moiety in the deoxygenation of alcohols and the allylation of ketones is also reported. Finally, the use of aromatic esters as robust, though easily removable, protecting groups is depicted. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.111

文献信息

• Regioselective Addition Reactions of Propargyl Bromides to Carbonyl Compounds with Gallium Catalyzed by Indium
  作者：Phil Ho Lee、Hyun Kim、Kooyeon Lee

  DOI：10.1002/adsc.200505046

  日期：2005.7

  propargyl bromides having substituents at the γ-position and gallium in the presence of 5 mol % of indium with aldehydes and ketones selectively produced homoallenyl alcohols in good to excellent yields. Treatment of organogallium reagents obtained from propargyl bromide or propargyl bromides having substituents at the α-position and gallium in the presence of 5 mol % of indium with carbonyl compounds selectively

  在5mol％的铟存在下，由在γ-位具有取代基的炔丙基溴和镓产生的有机镓试剂与醛和酮的反应选择性地以良好或优异的产率产生了高均烯基醇。在5mol％的铟存在下，用羰基化合物处理由在α位具有取代基的炔丙基溴或炔丙基溴和镓获得的有机镓试剂，选择性地得到高炔丙醇。
• Silver-Catalyzed Allenylation and Enantioselective Propargylation Reactions of Ketones
  作者：Benjamin L. Kohn、Naoko Ichiishi、Elizabeth R. Jarvo

  DOI：10.1002/anie.201206971

  日期：2013.4.15

  lining: Certain silver complexes are capable of selective catalysis of either allenylation or asymmetric propargylation reactions of ketones. Ligand‐free conditions lead to allenyl alcohols as the major product, whereas ligation with Walphos‐8 gives enantioenriched homopropargyl alcohols. This method can be applied to reactions of prochiral diarylketones to provide optically enriched tertiary diaryl alcohols

  不只是银衬：某些银络合物能够选择性催化酮的烯丙基化或不对称炔丙基化反应。无配体条件导致以烯丙醇为主要产物，而与Walphos-8的连接产生了对映体富集的高炔丙醇。该方法可用于前手性二芳基酮的反应以提供光学富集的叔二芳基醇。
• Palladium-Catalyzed Reaction of Propargylic Acetates with Carbonyl Compounds by SmI₂
  作者：Takanori Tabuchi、Junji Inanaga、Masaru Yamaguchi

  DOI：10.1246/cl.1987.2275

  日期：1987.11.5

  Reductive addition of propargylic acetates to carbonyl compounds proceeded smoothly at room temperature by using SmI2 and a catalytic amount of Pd(PPh3)4 to give the corresponding acetylenic and/or allenic alcohols with appreciable selectivity. The method is useful especially for the preparation of tri- and tetrasubstituted allenic alcohols.

  使用 SmI2 和一定量的 Pd(PPh3)4，丙炔基乙酸酯与羰基化合物的还原加成反应在室温下顺利进行，并以明显的选择性得到相应的乙炔醇和/或烯醇。该方法尤其适用于制备三取代和四取代的联烯醇。
• Zinc-Catalyzed Allenylations of Aldehydes and Ketones
  作者：Daniel R. Fandrick、Jaideep Saha、Keith R. Fandrick、Sanjit Sanyal、Junichi Ogikubo、Heewon Lee、Frank Roschangar、Jinhua J. Song、Chris H. Senanayake

  DOI：10.1021/ol202343c

  日期：2011.10.21

  The general zinc-catalyzed allenylation of aldehydes and ketones with an allenyl boronate Is presented. Preliminary mechanistic studies support a kinetically controlled process wherein, after a site-selective Ban exchange to generate a propargyl zinc intermediate, the addition to the electrophile effectively competes with propargyl-allenyl zinc equilibration. The utility of the methodology was demonstrated by application to a rhodium-catalyzed [4 + 2] cycloaddition.
• Zinc Amide Catalyzed Regioselective Allenylation and Propargylation of Ketones with Allenyl Boronate
  作者：Yasuhiro Yamashita、Yi Cui、Peizhong Xie、Shu̅ Kobayashi

  DOI：10.1021/acs.orglett.5b03045

  日期：2015.12.18

  Zinc amide catalyzed, regioselective allenylation and propargylation of ketones with allenyl boronate is reported. Tertiary allenyl and homopropargyl alcohols were obtained, respectively, in high selectivities, from the same starting materials, simply by changing the reaction conditions. The substrate scope was wide. Mechanistic studies suggest that the reactions are controlled under kinetic and thermodynamic conditions.