(2-((4-methoxyphenyl)ethynyl)phenyl)methanol | 405198-79-0

• 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-((4-methoxyphenyl)ethynyl)phenyl)methanol
• 英文别名: [2-[2-(4-Methoxyphenyl)ethynyl]phenyl]methanol；[2-[2-(4-methoxyphenyl)ethynyl]phenyl]methanol
• CAS: 405198-79-0
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: ZCKZWEQZISDSBG-UHFFFAOYSA-N

物化性质

• 熔点：
  99-100 °C
• 沸点：
  421.8±35.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

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-((4-methoxyphenyl)ethynyl)phenyl)methanol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到2-（2-（4-甲氧基苯基）乙炔基）苯甲醛
  参考文献：
  名称：

  钯催化的 2-炔基苯甲醛与芳基碘在甲醇中的酯化-氢芳基化反应

  摘要：

  在 Pd(PPh 3 ) 4 和 K 2 CO 3 存在下，2-炔基苯甲醛与芳基碘在甲醇回流下反应 24 小时，得到脱氢加成产物，即 2-(2,2-二取代-乙烯基)苯甲酸甲酯收益率适中；与环化产物一起，3-甲氧基-1-单取代-亚甲基-3-氢异苯并呋喃的产率为 3-18%。

  DOI：

  10.1055/s-2004-829056
• 作为产物：
  描述：

  2-碘苄醇 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 10.5h， 生成 (2-((4-methoxyphenyl)ethynyl)phenyl)methanol
  参考文献：
  名称：

  Cyclization reactions of 2-alkynylbenzyl alcohol and 2-alkynylbenzylamine derivatives promoted by tetrabutylammonium fluoride

  摘要：

  The regioselectivity of the cyclization reaction of 2-ethynylbenzyl alcohol and 2-ethynylbenzylamine derivatives promoted by TBAF was investigated. Six-membered ring derivatives were obtained from the compounds, which have a butyl group on the triple bond. Whereas five-membered ring products were afforded from the substrates having hydrogen or aromatic substituents. on the acetylene moiety. It was also concluded that both the tetrabutylammonium cation and fluoride anion were essential for the cyclization. Thus, the actual mechanism and catalytic cycle were also suggested. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00991-7

文献信息

• Stabilisation of Carbon-Supported Palladium Nanoparticles through the Formation of an Alloy with Gold: Application to the Sonogashira Reaction
  作者：Cybille Rossy、Jérôme Majimel、Eric Fouquet、Cyril Delacôte、Mohammed Boujtita、Christine Labrugère、Mona Tréguer-Delapierre、François-Xavier Felpin

  DOI：10.1002/chem.201300347

  日期：2013.10.11

  Oh my Gold! Gold atoms stabilise catalytically active palladium nanoparticles when engaged in an alloy heterogenised on carbon. The increased durability makes the Pd–Au/C catalyst more recyclable than the gold‐free Pd/C catalyst for the Sonogashira reaction.

  哦，天哪！当金原子与碳上异质化的合金结合后，它可以稳定具有催化活性的钯纳米粒子。耐用性的提高使Pd–Au / C催化剂比Sonogashira反应中的无金Pd / C催化剂更具可回收性。
• Catalytic Asymmetric Total Synthesis of (−)-Galanthamine and (−)-Lycoramine
  作者：Lei Li、Qiao Yang、Yuan Wang、Yanxing Jia

  DOI：10.1002/anie.201411338

  日期：2015.5.18

  conceptually new strategy featuring two metal‐catalyzed reactions as the key steps. A new method for the construction of 3,4‐fused benzofurans has been developed through a palladium‐catalyzed intramolecular Larock annulation reaction, which was successfully applied to the construction of the ABD tricyclic skeleton of 1 and 2. To achieve the asymmetric synthesis of 1 and 2, a ScIII/N,N′‐dioxide complex was used

  （-）-加兰他敏（1）和（-）-lycoramine（2）的催化不对称全合成反应已通过采用概念上新颖的策略来实现，该策略以两个金属催化的反应为关键步骤。通过钯催化的分子内Larock环化反应，开发了一种3,4-稠合苯并呋喃的构建新方法，该方法已成功应用于1和2的ABD三环骨架的构建。为了实现1和2的不对称合成，Sc III / N，N'-二氧化物络合物被用来催化3-烷基取代的苯并呋喃酮向甲基乙烯基酮的对映选择性共轭加成反应，以构建手性季碳中心。
• 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。
• Efficient Synthesis of Isothiochromene Derivatives by Pd-Catalyzed Hydrothiolation Reaction
  作者：Jie Feng、Meifang Lv、Guoping Lu、Chun Cai

  DOI：10.1002/ejoc.201402611

  日期：2014.8

  An efficient method for the preparation of isothiochromene derivatives through the palladium-catalyzed intramolecular hydrothiolation reaction of halides and thiourea is reported. Two carbon–sulfur bonds are formed in this one-pot palladium-catalyzed cascade reaction. This new protocol is free from foul-smelling thiols and operates under mild conditions to give isothiochromene derivatives in excellent

  报道了一种通过钯催化卤化物和硫脲的分子内氢硫醇化反应制备异硫色烯衍生物的有效方法。在这种一锅钯催化的级联反应中形成了两个碳硫键。这种新方案不含恶臭的硫醇，在温和条件下运行，以优异的产率和出色的 6-endo-dig 选择性提供异硫色烯衍生物。
• Fused-Ring Formation by an Intramolecular “Cut-and-Sew” Reaction between Cyclobutanones and Alkynes
  作者：Lin Deng、Likun Jin、Guangbin Dong

  DOI：10.1002/anie.201712487

  日期：2018.3.1

  alkynes to construct cyclohexenone‐fused rings is described herein. The challenge arises from the need for selective coupling at the more sterically hindered proximal position, and can be addressed by using an electron‐rich, but less bulky, phosphine ligand. The control experiment and 13C‐labelling study suggest that the reaction may start with cleavage of the less hindered distal C−C bond of cyclobutanones

  本文描述了在环丁酮和炔烃之间进行分子内“切割和缝合”催化转化以构建环己烯酮稠合环的过程。挑战来自在空间上受阻较大的近端位置进行选择性偶联的需求，可以通过使用富含电子但体积较小的膦配体来解决。对照实验和13 C标记研究表明，该反应可能始于裂解环丁烯酮受阻较少的远端C-C键，然后脱羰和CO重新插入以使Rh插入受阻较近的位置开始。