3-phenyl-1-(2-(p-tolylethynyl)phenyl)prop-2-yn-1-ol | 192935-78-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 3-phenyl-1-(2-(p-tolylethynyl)phenyl)prop-2-yn-1-ol
• CAS: 192935-78-7
• 化学式: C₂₄H₁₈O
• 分子量: 322.406
• InChiKey: XBSVCIMUDNLHRE-UHFFFAOYSA-N

物化性质

• 沸点：
  522.9±50.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-phenyl-1-(2-(p-tolylethynyl)phenyl)prop-2-yn-1-ol 在 三苯基膦氯金 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到(2-phenylnaphthalen-1-yl)(p-tolyl)methanone
  参考文献：
  名称：

  1，6-二炔-4-en-3-ols的金催化环异构化反应，形成萘基酮衍生物。

  摘要：

  我们报告了一种新的高效的金催化的1,6-diyne-4-en-3-ols环化反应，在环境条件下可得到萘基酮衍生物。这种环化的价值体现在其对多种醇底物的适用性上。

  DOI：

  10.1039/b618291g
• 作为产物：
  描述：

  4-碘甲苯 在 copper(l) iodide 、 四(三苯基膦)钯 三乙胺 作用下， 反应 1.0h， 生成 3-phenyl-1-(2-(p-tolylethynyl)phenyl)prop-2-yn-1-ol
  参考文献：
  名称：

  A Surprising Switch from the Myers–Saito Cyclization to a Novel Biradical Cyclization in Enyne–Allenes: Formal Diels–Alder and Ene Reactions with High Synthetic Potential

  摘要：

  AbstractIf there is an aryl substituent on the acetylene terminus of enyne‐allenes, then its reaction mode may be changed from the Myers‐Saito cyclization to a novel C2–C6 cyclization resulting in a net intramolecular Diels‐Alder or ene reaction. As a consequence, the thermal cyclization of readily accessible acyclic enyne‐allenes can be utilized for the synthesis of complex benzofulvene and benzofluorene derivatives. Kinetic results of the C2–C6 cyclization reaction indicate a two‐step reaction pathway with a benzofulvene biradical intermediate.

  DOI：

  10.1002/chem.19970030521

文献信息

• Gold-Catalyzed Cyclization of 1,6-Diyne-4-en-3-ols: Stannyl Transfer from 2-Tributylstannylfuran Through Au/Sn Transmetalation
  作者：Yifeng Chen、Ming Chen、Yuanhong Liu

  DOI：10.1002/anie.201201523

  日期：2012.6.18

  Gold‐tinted: A gold catalyzed cyclization reaction of 1,6‐diyne‐4‐en‐3‐ols, incorporating an in situ stannyl transfer reaction involving 2‐tributylstannylfuran, gives synthetically valuable 2‐stannylnaphthalenes (see scheme; DCE=dichloroethane). A gem‐diaurated furan complex, was isolated and fully characterized by X‐ray crystallographic analysis, and provides strong evidence for a tin to gold transmetalation

  金染色的：1,6-二炔-4-烯-3-醇的金催化环化反应，结合涉及2-三丁基锡烷基呋喃的原位锡烷基转移反应，产生了合成上有价值的2-锡烷基萘（见示意图; DCE =二氯乙烷） 。通过X射线晶体学分析分离出了一种由宝石渗析出的呋喃配合物，并对其进行了全面表征，并为从锡到金的过渡金属化步骤提供了有力的证据。
• Cobalt-catalyzed regioselective syntheses of indeno[2,1-<i>c</i>]pyridines from nitriles and diynes bearing propargyl fragments
  作者：Murong Xu、Zhong Zheng、Mengdan Wang、Lingkai Kong、Yujuan Ao、Yanzhong Li

  DOI：10.1039/c8ob02419g

  日期：——

  highly efficient CoI2/o-phenanthroline catalyzed cycloaddition reaction of diynes bearing TBS protected propargylic alcohol fragments with nitriles has been developed. This methodology offers regioselective access, with good functional group tolerance, to various indeno[2,1-c]pyridine derivatives in moderate to excellent yields. It was found that o-phenanthroline as a bidentate nitrogen ligand showed

  已开发出一种高效的CoI 2 /邻菲咯啉催化带有TBS保护的炔丙醇片段的丁炔与腈的环加成反应。该方法以中等至优异的产率提供了对多种茚并[2,1- c ]吡啶衍生物的区域选择性通路，具有良好的官能团耐受性。发现邻菲咯啉作为二齿氮配体在该环加成反应中显示出高功效。
• Gold-Catalyzed Cascade Cyclizations of 1,6-Diynyl Carbonates to Benzo[b]fluorenes Involving Arylation of Oxocarbenium Ion Intermediates and Decarboxylative Etherification
  作者：Yifeng Chen、Ming Chen、Yuanhong Liu

  DOI：10.1002/anie.201201799

  日期：2012.6.25

  cycloisomerizations give access to highly substituted benzo[b]fluorenes under mild reaction conditions (see scheme). Experimental results indicate that the in situ formed oxocarbenium ion intermediates, derived from gold‐catalyzed 3,3‐rearrangement and 6‐endo‐dig cyclization, undergo intramolecular arylation and subsequent decarboxylative etherification to furnish the final ether products.

  重排：在温和的反应条件下，所描述的金催化的环异构化反应可得到高度取代的苯并[ b ]芴（参见方案）。实验结果表明，在原位形成oxocarbenium离子中间体，衍生自金催化3,3-重排和6-内-挖环化，分子内经历芳基化和随后的脱羧醚化，得到最终的醚产物。
• Gold-Catalyzed Cascade Friedel-Crafts/Furan-Yne Cyclization/Heteroenyne Metathesis for the Highly Efficient Construction of Phenanthrene Derivatives
  作者：Yifeng Chen、Guijie Li、Yuanhong Liu

  DOI：10.1002/adsc.201000644

  日期：2011.2.11

  A rapid access to highly substituted phenanthrenyl ketones through gold-catalyzed cyclization of 1,6-diyn-4-en-3-ols with furans has been developed. Gold catalysts are effective to catalyze three cascade processes involving Friedel–Crafts/furan-yne cyclization/heteroenyne metathesis through CO bond and alkyne activation. This method offers several advantages such as high selectivities and easily accessible

  已经开发了通过呋喃与金催化的1,6-diyn-4-en-3-ols环化反应，快速获得高度取代的菲基酮的方法。金催化剂可有效地催化三个级联过程，包括通过CO键和炔烃活化进行的Friedel-Crafts /呋喃-炔环化/杂烯复分解。该方法具有许多优势，例如高选择性和易于获得的起始原料。
• Gold(I)-Catalyzed Regioselective Cyclization to Access Cyclopropane-Fused Tetrahydrobenzochromenes
  作者：Perla Bharath Kumar、Chittala Emmaniel Raju、Patel Hinal Chandubhai、Balasubramanian Sridhar、Galla V. Karunakar

  DOI：10.1021/acs.orglett.2c02564

  日期：2022.9.23

  Gold(I)-catalyzed efficient synthetic transformation was achieved to access the tetrahydrobenzo[h]cyclopropa[c]chromenes from allyl-substituted 1,6-diynes. Cyclopropane-fused tetrahydrobenzochromenes were obtained regioselectively in ≤92% yields. In this atom-economic organic transformation, three new C–C bonds were formed sequentially in one pot.

  实现了金（I）催化的高效合成转化，以从烯丙基取代的 1,6-二炔中获得四氢苯并[ h ]环丙[ c ]色烯。以≤92% 的产率区域选择性地获得了环丙烷稠合的四氢苯并色烯。在这种原子经济有机转化中，三个新的 C-C 键在一锅中依次形成。