1-bromo-2-phenylpent-4-yn-2-ol | 70987-14-3

• 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: 1-bromo-2-phenylpent-4-yn-2-ol
• 英文别名: 1-Brom-2-phenylpentin-4-ol-2
• CAS: 70987-14-3
• 化学式: C₁₁H₁₁BrO
• 分子量: 239.112
• InChiKey: NKFKZYWUCMIDRA-UHFFFAOYSA-N

物化性质

• 沸点：
  342.9±42.0 °C(Predicted)
• 密度：
  1.3246 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  1-bromo-2-phenylpent-4-yn-2-ol 、 氢氧化钾 以30%的产率得到
  参考文献：
  名称：

  SHIXIEV I. A.; KARAEV S. F.; KAZIEVA S. F.; DZHAFAROV D. S., AZERB. XIM. ZH., 1978, HO 6, 70-75

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴苯乙酮 、 allenylmagnesium bromide 生成 1-bromo-2-phenylpent-4-yn-2-ol
  参考文献：
  名称：

  SHIXIEV I. A.; KARAEV S. F.; KAZIEVA S. F.; DZHAFAROV D. S., AZERB. XIM. ZH., 1978, HO 6, 70-75

  摘要：

  DOI：

文献信息

• γ-Halo-enones: A Method for their Synthesis from Arylacyl Halides and Their Application to the Preparation of Five-Membered Ring Heterocycles
  作者：Mei-Huey Lin、Yen-Chih Huang、Chung-Kai Kuo、Chang-Hsien Tsai、Yi-Syuan Li、Ting-Chia Hu、Tsung-Hsun Chuang

  DOI：10.1021/jo5001274

  日期：2014.3.21

  A simple method has been developed for synthesis of γ-halo-enones. The approach employs a sequence involving initial indium-mediated allenylation reactions of phenacyl halides with propargyl bromide. This process is followed by acid-promoted rearrangement reactions of the formed homoallenic halohydrins. The new method can be incorporated into routes for the efficient synthesis of various five-membered

  已开发出一种简单的方法来合成γ-卤代烯酮。该方法采用的序列涉及初始的铟介导的苯甲酰卤与炔丙基溴的烯丙基化反应。该过程之后是形成的高烯丙基卤代醇的酸促进的重排反应。可以将新方法结合到有效合成各种五元杂环化合物的途径中。
• 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.
• Indium-mediated allylation/propargylation of α-diazoketones: a facile synthesis of 1-bromo-2-alkyl- or 2-arylpent-4-en-2-ols
  作者：J.S. Yadav、B.V. Subba Reddy、P. Vishnumurthy、Swapan Kr. Biswas

  DOI：10.1016/j.tetlet.2007.07.136

  日期：2007.9

  alpha-Diazoketones undergo smooth allylation with successive bromide insertion with allylindium bromide generated in situ from allyl bromide and indium metal to produce 1-bromo-2-alkyl- or 2-arylpent-4-en-2-ols in high yields. Addition of propargylindium bromide produces 1-bromo-2-alkyl-or 2-arylpent-4-yn-2-ols under similar conditions. (c) 2007 Published by Elsevier Ltd.