3-(4-methoxyphenyl)-1-(2-(phenylethynyl)phenyl)prop-2-yn-1-ol | 936855-54-8

• 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-(4-methoxyphenyl)-1-(2-(phenylethynyl)phenyl)prop-2-yn-1-ol
• CAS: 936855-54-8
• 化学式: C₂₄H₁₈O₂
• 分子量: 338.406
• InChiKey: LGSSLRIWWNRLIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-1-(2-(phenylethynyl)phenyl)prop-2-yn-1-ol 在 N-溴代丁二酰亚胺(NBS) 、 silver tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以69%的产率得到6-bromo-9-methoxy-11-phenyl-11H-benzo[a]fluoren-11-ol
  参考文献：
  名称：

  Novel Silver Tetrafluoroborate Catalyzed Electrophilic Cascade Cyclization Reaction: A Facile Approach to the Synthesis of Halo-Substituted Benzo[a]fluorenols

  摘要：

  A facile and novel silver tetrafluoroborate catalyzed electrophilic cascade cyclization reaction to generate halo-substituted benzo[a]fluorenols under mild conditions is disclosed. Good chemical selectivity and mild reaction conditions were involved in the transformation. The halide-containing benzo[a]fluorenols could be further elaborated via palladium-catalyzed cross-coupling reactions to introduce complexity.

  DOI：

  10.1021/ol301153t
• 作为产物：
  描述：

  苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 3-(4-methoxyphenyl)-1-(2-(phenylethynyl)phenyl)prop-2-yn-1-ol
  参考文献：
  名称：

  二炔醇与 (RO)2P(O)SH 串联环化直接合成苯并[b]芴基硫代磷酸酯

  摘要：

  通过简单制备的二炔醇和 (RO) 2 P(O)SH 的级联环化，开发了一种用于构建苯并 [ b ] 芴基硫代磷酸酯的通用且无金属方案，水是唯一的副产物。新的转化以丙二烯硫代磷酸酯为关键中间体，然后进行施密特型环化以获得所需的产物。值得注意的是，(RO) 2 P(O)SH 不仅作为亲核试剂，而且作为启动反应的酸促进剂。

  DOI：

  10.1021/acs.orglett.3c00009

文献信息

• Gold-Catalyzed Oxidative Cyclizations of {<i>o</i>-(Alkynyl)phenyl propargyl} Silyl Ether Derivatives Involving 1,2-Enynyl Migration: Synthesis of Functionalized 1<i>H</i>-Isochromenes and 2<i>H</i>-Pyrans
  作者：Jidong Zhao、Wei Xu、Xin Xie、Ning Sun、Xiangdong Li、Yuanhong Liu

  DOI：10.1021/acs.orglett.8b02380

  日期：2018.9.7

  A new and convenient strategy for the synthesis of functionalized 1H-isochromene and 2H-pyran derivatives based on gold-catalyzed oxidative cyclizations of o-(alkynyl)phenyl propargyl ether derivatives has been developed. The reaction proceeds via gold-catalyzed highly regioselective oxidation, followed by 1,2-migration of an enynyl group and nucleophlic addition. Isocoumarins were also constructed

  基于金催化的邻-（炔基）苯基炔丙基醚衍生物的氧化环化反应，开发了一种新的方便的合成功能化的1 H-异戊二烯和2 H-吡喃衍生物的策略。该反应通过金催化的高度区域选择性氧化进行，然后进行烯键基的1，2-迁移和核苷加成。还通过氧化裂解所获得的1 H-异色酮的环外双键来构建异香豆素。
• Gold-catalyzed cyclo-isomerization of 1,6-diyne-4-en-3-ols to form naphthyl ketone derivatives
  作者：Jian-Jou Lian、Rai-Shung Liu

  DOI：10.1039/b618291g

  日期：——

  We report a new efficient gold-catalyzed cyclization of 1,6-diyne-4-en-3-ols to give naphthyl ketone derivatives under ambient conditions. The value of this cyclization is reflected by its applicability to a wide range of alcohol substrates.

  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。
• <i>Exo</i>-<i>Dig</i>Radical Cascades of Skipped Enediynes: Building a Naphthalene Moiety within a Polycyclic Framework
  作者：Kamalkishore Pati、Audrey M. Hughes、Hoa Phan、Igor V. Alabugin

  DOI：10.1002/chem.201304092

  日期：2014.1.7

  Cascade radical transformations of acyclic precursors open efficient, convenient and atom‐economical access to functionalized compounds of increased structural complexity. This report describes a selective sequence of 5‐exo‐dig and 6‐exo‐dig cyclizations followed by attack at a pendant aromatic moiety and rearomatization.

  无环前体的级联自由基转化为结构复杂性增加的功能化化合物提供了高效，便捷和原子经济的途径。本报告介绍了5 exo - dig和6 exo - dig环化的选择性序列，然后攻击侧链芳族部分并进行了重新芳构化。
• Gold-catalyzed cyclization of 1,6-diynyl dithioacetals via 1,7-carbene transfer and aromatic C–H functionalization
  作者：Wei Xu、Ming Chen、Ning Sun、Yuanhong Liu

  DOI：10.1039/c6cc05302e

  日期：——

  A gold-catalyzed cyclization of 1,6-diynyl dithioacetals has been developed, which provides an attractive route to diverse-substituted benzo[a]fluorene derivatives. The reaction is initiated through 1,2-sulfur migration of propargyl dithioacetal moiety to...

  已经开发了金催化的1，6-二炔基二硫缩醛的环化，这为各种取代的苯并[a]芴衍生物提供了诱人的途径。该反应是通过炔丙基二硫缩醛部分的1,2-硫迁移至...
• TBAF-Catalyzed Cyclization Reactions of <i>o</i> -(Alkynyl)phenyl Propargyl Alcohols with Malonate Esters: A Possible Cation-π Interaction as The Activation Approach
  作者：Yulei Zhao、Xuqiang Guo、Zongkang Wang、Duyi Shen、Tingting Chen、Nan Wu、Shina Yan、Jinmao You

  DOI：10.1002/ejoc.201901790

  日期：2020.2.28

  method has been devised for the synthesis of dihydroisobenzofuran derivatives through the reaction of in situ generated ynones with potentially C‐nucleophilic malonate esters. Both the basicity of fluoride anion and ammonium cation–π interaction with alkyne unit might play a crucial role in the cyclization reaction.

  通过原位产生的炔酮与潜在的C-亲核丙二酸酯的反应，已设计出一种有效的方法来合成二氢异苯并呋喃衍生物。氟阴离子和与阳离子单元的铵阳离子-π相互作用的碱性都可能在环化反应中起关键作用。