4-methyl-1-phenyl-5-hexyn-3-ol | 103934-05-0

• 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: 4-methyl-1-phenyl-5-hexyn-3-ol
• 英文别名: 4-methyl-1-phenylhex-5-yn-3-ol
• CAS: 103934-05-0；103934-12-9
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: VJVUCUFOJRVKRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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-methyl-1-phenyl-5-hexyn-3-ol 在 Lindlar catalyst potassium fluoride 、 lithium aluminium tetrahydride 、 正丁基锂 、 氢气 、 氧气 、 对甲苯磺酸 、 臭氧 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 19.02h， 生成 2,2,5-trimethyl-4-(2-phenylethyl)-1,3-dioxane
  参考文献：
  名称：

  Scope and stereochemical course of the addition of (trimethylsilyl)allenes to ketones and aldehydes. A regiocontrolled synthesis of homopropargylic alcohols

  摘要：

  DOI：

  10.1021/jo00370a023
• 作为产物：
  描述：

  苯丙醛 、 3-丁炔-2-甲烷磺酸盐 在 palladium diacetate diethylzinc 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以54%的产率得到4-methyl-1-phenyl-5-hexyn-3-ol
  参考文献：
  名称：

  Second-Generation Synthesis of the Polypropionate Subunit of Callystatin A Based on Regioselective Internal Alkyne Hydrostannation

  摘要：

  [GRAPHICS]An improved route to the polypropionate segment of callystatin A is described in which the efficient directed hydrostannation of an internal alkyne and subsequent iodinolysis provides a key vinylic iodide intermediate.

  DOI：

  10.1021/ol026791m

文献信息

• Photoredox Propargylation of Aldehydes Catalytic in Titanium
  作者：Francesco Calogero、Andrea Gualandi、Marco Di Matteo、Simone Potenti、Andrea Fermi、Giacomo Bergamini、Pier Giorgio Cozzi

  DOI：10.1021/acs.joc.1c00521

  日期：2021.5.7

  A practical and effective photoredox propargylation of aldehydes promoted by 10 mol % of [Cp2TiCl2] is presented. No stoichiometric metals or scavengers are used for the process. A catalytic amount of the cheap and simply prepared organic dye 3DPAFIPN is used as the reductant for titanium. The reaction displayed a broad scope, and no traces of allenyl isomers were detected for simple propargyl bromide

  提出了一种实用且有效的由10 mol％的[Cp 2 TiCl 2 ]促进的醛的光氧化还原炔丙基化。该过程不使用化学计量的金属或清除剂。催化量的廉价且简单制备的有机染料3DPAFIPN用作钛的还原剂。该反应显示范围广，对于简单的炔丙基溴，未检测到痕量的烯丙基异构体，而对于取代的炔丙基溴，未观察到炔丙基和烯丙基异构体的混合物。
• Selective Formation of Propargylsilanes and Allenylsilanes and Their Reactions with Aldehydes for the Preparation of Homopropargylic and Allenic Alcohols
  作者：Shu Kobayashi、Koichi Nishio

  DOI：10.1021/ja00128a043

  日期：1995.6
• An effective and selective conjugate propargylation reaction of stannylallenes to .alpha.,.beta.-unsaturated carbonyl compounds and .alpha.-nitro olefins
  作者：Junichi Haruta、Koichi Nishi、Satoshi Matsuda、Shuji Akai、Yasumitsu Tamura、Yasuyuki Kita

  DOI：10.1021/jo00303a019

  日期：1990.8
• Scope and stereochemical course of the addition of (trimethylsilyl)allenes to ketones and aldehydes. A regiocontrolled synthesis of homopropargylic alcohols
  作者：Rick L. Danheiser、David J. Carini、Carrie A. Kwasigroch

  DOI：10.1021/jo00370a023

  日期：1986.10
• Second-Generation Synthesis of the Polypropionate Subunit of Callystatin A Based on Regioselective Internal Alkyne Hydrostannation
  作者：James A. Marshall、Matthew P. Bourbeau

  DOI：10.1021/ol026791m

  日期：2002.10.1

  [GRAPHICS]An improved route to the polypropionate segment of callystatin A is described in which the efficient directed hydrostannation of an internal alkyne and subsequent iodinolysis provides a key vinylic iodide intermediate.