2-(phenylethynyl)benzhydrol | 221458-84-0

• 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: 2-(phenylethynyl)benzhydrol
• 英文别名: phenyl(2-(phenylethynyl)phenyl)methanol；Phenyl(2-(phenyleth-ynyl)phenyl)methanol；phenyl-[2-(2-phenylethynyl)phenyl]methanol
• CAS: 221458-84-0
• 化学式: C₂₁H₁₆O
• 分子量: 284.357
• InChiKey: JDVKFAZNQPHSRD-UHFFFAOYSA-N

物化性质

• 熔点：
  99-101 °C
• 沸点：
  476.3±33.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  2-(phenylethynyl)benzhydrol 在 水 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以40%的产率得到2,3-二苯基-1-二氢茚酮
  参考文献：
  名称：

  Molecular iodine mediated cyclization reactions of 2-(1-alkynyl)benzylic alcohols to substituted indenones

  摘要：

  efficient I-2-mediated approach to the synthesis of disubstituted indenones from readily available 2-alkynylbenzyl alcohols in the presence of H2O has been developed. These results are different from the known iodocyclization reactions in which O-containing heterocycles are obtained. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.030
• 作为产物：
  描述：

  邻溴苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 生成 2-(phenylethynyl)benzhydrol
  参考文献：
  名称：

  Ni-Catalyzed Intramolecular Cycloaddition of Methylenecyclopropanes to Alkynes

  摘要：

  Ni-catalyzed intramolecular cycloaddition of methylenecyclopropanes (MCPs) to arkylalkynes via proximal bond cleavage is reported. The reaction provides a facile route for the preparation of cyclopenta[a]indene derivatives.

  DOI：

  10.1021/ol1028628

文献信息

• Redox-triggered hydroarylation of o-(hydroxyalkyl)arylalkynes with arylsulfonyl chlorides using visible light catalysis
  作者：Renjie Song、Jiadong Xia、Jiangxi Yu、Jinheng Li

  DOI：10.1007/s11426-015-5529-0

  日期：2016.2

  A new radical-mediated method for the synthesis of 1-(2-(1,2-diarylvinyl)phenyl)ethan-1-ones by the redox hydroarylation of o-(hydroxyalkyl)arylalkynes with arylsulfonyl chlorides is described. This visible light catalysis method proceeds via a sequence of the radical addition of aryl group across the C-C triple bond, protonation and redox reaction, and represents a new redox transformation reaction directed by a neighboring hydroxyl group.

  报道了一种通过邻（羟基烷基）芳基炔与芳基磺酰氯的氧化性氢芳基化反应，合成1-(2-(1,2-二芳基乙烯)苯基)乙酮的新型自由基介导方法。该可见光催化方法通过一系列反应过程实现，包括芳基团对碳-碳叁键的自由基加成、质子化和氧化还原反应，并代表了一种由邻位羟基引导的新型氧化还原转化反应。
• Synthesis of Functionalized 1<i>H</i>-Indenes via Copper-Catalyzed Arylative Cyclization of Arylalkynes with Aromatic Sulfonyl Chlorides
  作者：Xiaoming Zeng、Laurean Ilies、Eiichi Nakamura

  DOI：10.1021/ja209300c

  日期：2011.11.9

  with commercially available aromatic sulfonyl chlorides that function as an aryl group donor. The reaction tolerates a broad range of functional groups, including bromide and iodide, nitrile, ketone, and nitro groups. The reaction allowed the synthesis of polycyclic aromatic hydrocarbons, such as a bis(indene), indacene, and fused polyarene derivatives, some of them showing strong fluorescence in solution

  多种多取代的 1H-茚可以通过铜催化的简单芳炔与用作芳基供体的市售芳族磺酰氯的芳基化环化反应来制备。该反应耐受广泛的官能团，包括溴化物和碘化物、腈、酮和硝基。该反应允许合成多环芳烃，例如双（茚）、茚和稠合聚芳烃衍生物，其中一些在溶液和固态中显示出强烈的荧光。
• Synthesis of dibenzocyclohepta[1,2-<i>a</i>]naphthalene derivatives from phenylacetaldehyde and alkynyl benzyl alcohols <i>via</i> sequential electrophilic addition and double Friedel–Crafts reactions
  作者：Archana K. Sahu、Ramanjaneyulu Unnava、Bipin K. Behera、Anil K. Saikia

  DOI：10.1039/d1ob00057h

  日期：——

  been developed for the synthesis of substituted 9H-dibenzo[3,4:6,7]-cyclohepta[1,2-a]naphthalenes from phenylacetaldehydes and ortho-alkynyl benzyl alcohols in the presence of a Lewis acid in moderate to good yields within a short reaction time. Interestingly, the reaction proceeds through a highly regioselective electrophilic addition followed by double Friedel–Crafts reaction to form uncommon dibenzo-fused

  已经开发了一种简单的方法，用于在路易斯酸存在下，由苯乙醛和邻炔基苄基醇合成取代的9 H-二苯并[3,4：6,7]-环庚[1,2- a ]萘。在较短的反应时间内中度到良好的收率。有趣的是，该反应是通过高度区域选择性的亲电加成反应进行的，然后进行两次Friedel-Crafts反应，形成不常见的二苯并稠合的七元碳环。
• Intramolecular Reductive Double Cyclization of <i>o</i>,<i>o</i>′-Bis(arylcarbonyl)diphenylacetylenes: Synthesis of Ladder π-Conjugated Skeletons
  作者：Hongyu Zhang、Takashi Karasawa、Hiroshi Yamada、Atsushi Wakamiya、Shigehiro Yamaguchi

  DOI：10.1021/ol901148p

  日期：2009.7.16

  reduction dominantly occurs over the acetylene reduction. The produced bis(radical anion) intermediate undergoes a synchronous double-radical 5-endo-dig cyclization. This simple reduction procedure produces two intriguing classes of ladder π-conjugated skeletons, i.e., emissive methylene-bridged stilbenes and dibenzo[a,e]pentalenes regarded as a cyclic 1,4-diphenylbutadiene.

  用萘二甲酸锂处理双（芳基羰基）二苯基乙炔时，羰基还原反应主要发生在乙炔还原反应之上。产生的双（自由基阴离子）中间体经历同步的双自由基5-内切-挖掘环化。这种简单的还原过程产生了两个有趣的梯形π共轭骨架，即被认为是环状1,4-二苯基丁二烯的亚甲基桥联发光苯乙烯和二苯并[ a，e ]戊烯。
• Tandem C-3/C-2 annulation of indole, benzofuran, and benzothiophene with 2-alkynyl benzylalcohol: an efficient approach to the diverse tetracyclic heteroazulene ring systems
  作者：Soumen Sarkar、Krishnendu Bera、Umasish Jana

  DOI：10.1016/j.tetlet.2014.09.050

  日期：2014.11

  We demonstrate an efficient and flexible strategy toward the synthesis of a library of biologically and pharmaceutically important tetracyclic heteroazulene derivatives in the presence of inexpensive and less toxic molecular iodine. The present strategy involves a sequential alkylation and alkenylation of indole/benzofuran/benzothiophene with o-alkynyl benzyl alcohols derivatives to obtain tetracyclic

  我们展示了在廉价和毒性较小的分子碘存在下合成生物学和药学上重要的四环杂氮杂烯衍生物文库的有效而灵活的策略。本策略涉及用邻-炔基苄醇衍生物对吲哚/苯并呋喃/苯并噻吩进行顺序烷基化和烯基化，以中等至良好的产率获得四环杂氮杂烯衍生物。与其他方法相比，当前策略更加通用，通用且对环境友好。