1-[2-(p-tolylethynyl)phenyl]pentan-1-ol | 1205555-52-7

• 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-[2-(p-tolylethynyl)phenyl]pentan-1-ol
• 英文别名: 1-[2-[2-(4-Methylphenyl)ethynyl]phenyl]pentan-1-ol
• CAS: 1205555-52-7
• 化学式: C₂₀H₂₂O
• 分子量: 278.394
• InChiKey: RKVGQMDXRSLRBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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-[2-(p-tolylethynyl)phenyl]pentan-1-ol 在 bismuth(lll) trifluoromethanesulfonate 、 叠氮基三甲基硅烷 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 1.0h， 生成 8-butyl-3-(p-tolyl)-8H-[1,2,3]triazolo[5,1-a]isoindole
  参考文献：
  名称：

  由邻炔基苯甲醛和叠氮化三甲基硅一锅合成三唑稠合的异吲哚

  摘要：

  据报道，由邻炔基苯甲醛和三甲基硅烷基叠氮化物（TMSN 3）有效地一锅法合成1,2,3-三唑稠合的异吲哚。该反应通过形成二叠氮化物中间体和随后的分子内叠氮化物-炔烃环加成反应而进行，从而提供了一种新颖的途径来获得各种8-azido-8 H- [1,2,3] triazolo [5,1- a ] isoindoles高产。

  DOI：

  10.1016/j.tetlet.2018.03.002
• 作为产物：
  描述：

  正丁基锂 、 2-[ 2 -(4-甲基苯基)乙炔基]苯甲醛 以 四氢呋喃 、 正戊烷 为溶剂， 以6.6 g的产率得到1-[2-(p-tolylethynyl)phenyl]pentan-1-ol
  参考文献：
  名称：

  A Simple and Mild Synthesis of 1H-Isochromenes and (Z)-1-Alkylidene-1,3-dihydroisobenzofurans by the Iodocyclization of 2-(1-Alkynyl)benzylic Alcohols

  摘要：

  A variety of iodo-substituted isochromenes, dihydroisobenzofurans, and pyranopyridines are readily prepared in good to excellent yields under mild conditions by the iodocyclization of readily available 2-(1-alkynyl)benzylic alcohols or 2-(1-alkynyl)-3-(hydroxymethyl)pyridines. Reactions are carried out in MeCN at 25 degrees C with 3 equiv of I-2 as the iodine source and NaHCO3 (3 equiv) as the base. The regiochemical outcome of the reaction strongly depends on the substitution pattern of the starting material. In particular, the 5-exo-dig cyclization mode, leading to dihydroisobenzofurans, is observed in the case of substrates bearing a tertiary alcoholic group, owing to the gem-dialkyl effect, while the 6-endo-dig cyclization mode, leading to isochromene or pyranopyridines, is the usually preferred pathway in the case of substrates bearing a primary or secondary alcoholic group.

  DOI：

  10.1021/jo902333y

文献信息

• A Simple and Mild Synthesis of 1<i>H</i>-Isochromenes and (<i>Z</i>)-1-Alkylidene-1,3-dihydroisobenzofurans by the Iodocyclization of 2-(1-Alkynyl)benzylic Alcohols
  作者：Raffaella Mancuso、Saurabh Mehta、Bartolo Gabriele、Giuseppe Salerno、William S. Jenks、Richard C. Larock

  DOI：10.1021/jo902333y

  日期：2010.2.5

  A variety of iodo-substituted isochromenes, dihydroisobenzofurans, and pyranopyridines are readily prepared in good to excellent yields under mild conditions by the iodocyclization of readily available 2-(1-alkynyl)benzylic alcohols or 2-(1-alkynyl)-3-(hydroxymethyl)pyridines. Reactions are carried out in MeCN at 25 degrees C with 3 equiv of I-2 as the iodine source and NaHCO3 (3 equiv) as the base. The regiochemical outcome of the reaction strongly depends on the substitution pattern of the starting material. In particular, the 5-exo-dig cyclization mode, leading to dihydroisobenzofurans, is observed in the case of substrates bearing a tertiary alcoholic group, owing to the gem-dialkyl effect, while the 6-endo-dig cyclization mode, leading to isochromene or pyranopyridines, is the usually preferred pathway in the case of substrates bearing a primary or secondary alcoholic group.
• One-pot synthesis of triazole-fused isoindoles from o-alkynylbenzaldehydes and trimethylsilyl azide
  作者：Noriko Okamoto、Takuya Sueda、Hideki Minami、Reiko Yanada

  DOI：10.1016/j.tetlet.2018.03.002

  日期：2018.4

  An efficient one-pot synthesis of 1,2,3-triazole-fused isoindoles from o-alkynylbenzaldehydes and trimethylsilyl azide (TMSN3) is reported. The reaction proceeds through the formation of a diazide intermediate and a subsequent intramolecular azide-alkyne cycloaddition, providing a novel access to a variety of 8-azido-8H-[1,2,3]triazolo[5,1-a]isoindoles in high yields.

  据报道，由邻炔基苯甲醛和三甲基硅烷基叠氮化物（TMSN 3）有效地一锅法合成1,2,3-三唑稠合的异吲哚。该反应通过形成二叠氮化物中间体和随后的分子内叠氮化物-炔烃环加成反应而进行，从而提供了一种新颖的途径来获得各种8-azido-8 H- [1,2,3] triazolo [5,1- a ] isoindoles高产。