<2-<2-(2-Methoxyphenyl)ethynyl>phenyl>methanol | 166757-00-2

• 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-<2-(2-Methoxyphenyl)ethynyl>phenyl>methanol
• 英文别名: (2-((2-methoxyphenyl)ethynyl)phenyl)methanol；(2-(2-(2-methoxyphenyl)ethynyl)phenyl)methanol；2-(2-(2-Methoxyphenyl)ethynyl)phenylmethanol；[2-[2-(2-methoxyphenyl)ethynyl]phenyl]methanol
• CAS: 166757-00-2
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: VHEWUBNTTCKYMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  <2-<2-(2-Methoxyphenyl)ethynyl>phenyl>methanol 在 溴 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 C₁₆H₁₃BrO
  参考文献：
  名称：

  (2-炔基苯基) 苄基醚的碱催化顺序 5-exo-dig/7-endo-dig 环化：范围、机理研究和光物理性质

  摘要：

  通过连续叔丁醇钾催化的一锅环化，以高度选择性的方式从 (2-炔基苯基) 苄基醚合成了稠合到七元环的杂环。

  DOI：

  10.1002/ejoc.202200984
• 作为产物：
  描述：

  2-(三甲基甲硅烷基乙炔基)苯甲醚 在 copper(l) iodide 、 bis(triphenylphosphine)palladium(II)-chloride 、 四丁基氟化铵 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 <2-<2-(2-Methoxyphenyl)ethynyl>phenyl>methanol
  参考文献：
  名称：

  An Unusual Example of a 6-Endo-Dig Addition to an Unactivated Carbon-Carbon Triple Bond

  摘要：

  Methyl 2-[2-[2-(1-hydroxy-1-ethyl)phenyl]ethynyl]benzoate was prepared as an intermediate for subsequent conversion to an a-diazo ketone. Under the basic conditions used to hydrolyze the methyl ester, the neighboring hydroxyl functionality underwent reaction with the unactivated acetylenic group, producing a benzopyranyl-substituted alpha-diazoacetophenone. Treatment of this diazocarbonyl compound with a catalytic quantity of rhodium(II) mandelate afforded a novel dibenzo[a,e]cyclononenone derivative. The reaction proceeds via an initially formed oxonium ylide which rearranges further by means of a 1,2-alkyl shift. A prime factor in determining the direction of internal cyclization to the triple bond is the presence of the carbomethoxy group in the ortho position of the beta-phenyl ring. Thus, in contrast with related systems which exhibit a clear preference for 5-exo-dig cyclization at the acetylenic center, the 6-endo-dig addition is the preferred pathway for the o-formyl- and o-carbomethoxy-substituted alkynyl alcohols. Careful monitoring of the reaction actually showed that the reaction proceeds by initial formation of the 5-exo-dig product followed by a novel rearrangement to the 6-endo product.

  DOI：

  10.1021/jo00122a047

文献信息

• 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。
• Regioselective synthesis of phthalans via Cu(OTf)2-catalyzed 5-exo-dig intramolecular hydroalkoxylation of 2-(ethynyl)benzyl alcohols
  作者：Chandrasekaran Praveen、Chandran Iyyappan、Paramasivan Thirumalai Perumal

  DOI：10.1016/j.tetlet.2010.07.030

  日期：2010.9

  efficient, regioselective Cu(OTf)2-catalyzed 5-exo-dig intramolecular hydroalkoxylation of 2-(ethynyl)benzyl alcohol, which provides a concise access to functionalized phthalan in high yields has been developed. A wide range of substrates possessing terminal, internal, and heteroaromatic alkynes can be efficiently transformed into the targeted phthalans. Substrates with primary, secondary, and tertiary benzyl

  一种高效，区域选择性的Cu（OTF）2催化的5-外型-挖2-（乙炔基）苄醇，它提供一个简明的访问以高收率官能phthalan的分子内hydroalkoxylation已经研制成功。具有末端，内部和杂芳族炔烃的多种底物可以有效地转化为目标邻苯二甲酸酯。具有伯，仲和叔苄醇的底物也进展良好，以高收率生产了相应的邻苯二甲酸酯。不论底物的性质如何，当区域选择性成为一个问题时，环化反应都遵循高度选择性的5- exo - dig区域化学。
• Regioselective synthesis and evaluation of 3-alkylidene-1, 3-dihydroisobenzofurans as potential antidepressant agents
  作者：C PRAVEEN、C IYYAPPAN、K GIRIJA、K SURESH KUMAR、P T PERUMAL

  DOI：10.1007/s12039-011-0150-z

  日期：2012.3

  3-Alkylidene-1,3-dihydroisobenzofurans exhibited moderate antidepressant activity as evaluated by forced swim and tail suspension test methods. Virtual screening was carried out by docking the designed compounds into the serotonin binding sites of arabinase protein to predict the analogue binding mode of the compounds to the SSRIs.

  3-亚烷基-1,3-二氢异苯并呋喃在强迫游泳和尾悬试验方法的评估中表现出中等程度的抗抑郁活性。通过将设计的化合物与阿拉伯蛋白酶的血清素结合位点对接，进行了虚拟筛选，以预测化合物与 SSRIs 的类似结合模式。
• Synthesis of 2-Aryl Acetophenones via Hydrobromination and Oxy-isomerization of (<i>o</i>-Arylethynyl)benzyl Alcohols
  作者：Tzu-Hsuan Kuan、Duen-Ren Hou

  DOI：10.1021/acs.joc.1c00294

  日期：2021.5.7

  Hydrobromination and oxy-isomerization of (o-arylethynyl)benzyl alcohols to yield brominated aryl ketones were achieved with bromotrimethylsilane. The substrate scope suggested that vinyl carbocations, stabilized by the conjugated aryl groups, are the reaction intermediates. 1H-Isochromene was also detected by 1H NMR, and an isolated 1H-isochromene was converted to the product when retreated with TMSBr

  用溴代三甲基硅烷实现了（邻-芳基乙炔基）苄醇的氢溴化和氧异构化，生成溴化的芳基酮。底物范围表明，通过共轭芳基稳定的乙烯基碳阳离子是反应中间体。还通过1 H NMR检测到1 H-异戊二烯，当用TMSBr处理时，分离出的1 H-异戊二烯转化为产物。1 H-异戊二烯的形成等同于6-内挖-环化，并与在基本条件下的相应反应形成对比，在该条件下，以5-外-挖为主导。
• Selective cyclization of alkynols and alkynylamines catalyzed by potassium tert-butoxide
  作者：Deng Yuan Li、Ke Ji Shi、Xiao Feng Mao、Zheng Le Zhao、Xin Yan Wu、Pei Nian Liu

  DOI：10.1016/j.tet.2014.06.078

  日期：2014.9