3-hydroxy-4-cyclohexylethynylbenzene | 1174270-86-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-hydroxy-4-cyclohexylethynylbenzene
• 英文别名: 2-(2-Cyclohexylethynyl)phenol
• CAS: 1174270-86-0
• 化学式: C₁₄H₁₆O
• 分子量: 200.28
• InChiKey: DISRMQXXDYZVJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  3-hydroxy-4-cyclohexylethynylbenzene 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 氢气 、 potassium carbonate 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 39.0h， 生成 (-)-(E)-3-cyclohexylmethylene-2-isopropenyl-2,3-dihydrobenzofuran
  参考文献：
  名称：

  Rhodium-Catalyzed Olefin Isomerization/Enantioselective Intramolecular Alder-Ene Reaction Cascade

  摘要：

  The olefin isomerization/enantioselective intramolecular Alder-ene reaction cascade was achieved by using a cationic rhodium(I)/(R)-BINAP complex as a catalyst. A variety of substituted dihydrobenzofurans and dihydronaphthofurans were obtained from phenol- or naphthol-linked 1,7-enynes, respectively, with good yields and ee values.

  DOI：

  10.1021/ol201986e
• 作为产物：
  描述：

  1-(cyclohexylethynyl)-2-(methoxymethoxy)benzene 在 盐酸 作用下， 以 四氢呋喃 、 水 、 异丙醇 为溶剂， 反应 16.0h， 生成 3-hydroxy-4-cyclohexylethynylbenzene
  参考文献：
  名称：

  Rhodium-Catalyzed Olefin Isomerization/Enantioselective Intramolecular Alder-Ene Reaction Cascade

  摘要：

  The olefin isomerization/enantioselective intramolecular Alder-ene reaction cascade was achieved by using a cationic rhodium(I)/(R)-BINAP complex as a catalyst. A variety of substituted dihydrobenzofurans and dihydronaphthofurans were obtained from phenol- or naphthol-linked 1,7-enynes, respectively, with good yields and ee values.

  DOI：

  10.1021/ol201986e

文献信息

• Gold-Catalyzed Fluorination-Hydration: Synthesis of α-Fluorobenzofuranones from 2-Alkynylphenol Derivatives
  作者：Qiang Wang、Yu Jiang、Run Sun、Xiang-Ying Tang、Min Shi

  DOI：10.1002/chem.201602545

  日期：2016.10.4

  The AuI‐catalyzed fluorination–hydration of 2‐alkynylphenol derivatives in the presence of Selectfluor [1‐chloromethyl‐4‐fluoro‐1,4‐diazoniabicyclo‐[2.2.2]octane bis(tetrafluoroborate)] has been developed. This method provides straightforward access to α‐fluorobenzofuranones with the construction of C−O, C=O, and C−F bonds in a single step on the basis of an AuI/AuIII redox catalytic cycle. Several

  在Au我催化的2- alkynylphenol衍生物的氟化水合的Selectfluor的存在[1-氯甲基-4-氟-1,4- diazoniabicyclo- [2.2.2]辛烷双（四氟硼酸盐）]已被开发。该方法可在Au I / Au III氧化还原催化循环的基础上，一步一步直接获得具有C-O，C = O和C-F键的α-氟苯并呋喃酮。还进行了一些对照实验，包括该反应的不对称变体，以深入了解反应机理。
• Meyer–Schuster-Type Rearrangement of Propargylic Alcohols into α-Selenoenals and -enones with Diselenides
  作者：Yong-Liang Ban、Long You、Kai-Wen Feng、Fei-Cen Ma、Xiao-Ling Jin、Qiang Liu

  DOI：10.1021/acs.joc.1c00167

  日期：2021.4.2

  preparation of a diverse array of multisubstituted α-selenoenals and -enones from readily accessible propargylic alcohols and diselenides. The transformation proceeds via the Selectfluor-promoted selenirenium pathway, which enables selenenylation/rearrangement of a variety of propargylic alcohols. Gram-scale experiments showed the potential of this synergistic protocol for practical application.

  我们描述了一种温和且广泛适用的方案，用于从易于获得的炔丙醇和二硒化物制备多种多样的多取代的α-硒烯醛和-烯酮阵列。转化通过Selectfluor促进的硒鎓途径进行，该途径可实现各种炔丙醇的硒烯基化/重排。克级实验显示了这种协同协议在实际应用中的潜力。
• Synthesis of novel oxygen heterocycles: 1,10-dioxa-cyclopenta[a]fluorene and benzo[b]naphtho[2, 1-d]furans via Dötz intramolecular benzannulation
  作者：Subhabrata Sen、Parag Kulkarni、Kailaskumar Borate、Nandini R. Pai

  DOI：10.1016/j.tetlet.2009.04.123

  日期：2009.7

  Novel fused heterocycles 1,10-dioxa-cyclopenta[a]fluorene and benzo[b]naphtho[2, 1-d]furans were synthesized via Dötz intramolecular benzannulation of alkyne tethered aryloxy chromium Fischer carbenes.

  新型的稠合杂环1,10-二氧杂环戊[ a ]芴和苯并[ b ]萘[2,1- d ]呋喃是通过炔烃系芳氧基铬菲舍尔苯甲酸酯的Dötz分子内苯环化反应合成的。
• An Annulative Electrophilic Amination Approach to 3-Aminobenzoheteroles
  作者：Naoki Matsuda、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/jo202207s

  日期：2012.1.6

  A copper-catalyzed annulative amination approach to 3-aminobenzofurans and -indoles from o-alkynylphenols and -anilines has been developed. The Cu-based catalysis is based on an umpolung, electrophilic amination with O-benzoyl hydroxylamines and enables the mild and convergent synthesis of various 3-aminobenzoheteroles of biological and pharmaceutical interest. Some mechanistic investigations and an application of this protocol to construction of more complex tricyclic framework are also described.
• Copper-Mediated Annulative Direct Coupling of <i>o</i>-Alkynylphenols with Oxadiazoles: A Dehydrogenative Cascade Construction of Biheteroaryls
  作者：Hitoshi Hachiya、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/ol200975j

  日期：2011.6.17

  A copper-mediated annulative direct coupling of o-alkynylphenols with 1,3,4-oxadiazoles proceeds smoothly even under ambient conditions to afford the corresponding biheteroaryls. The reaction system represents a new avenue for the construction of biheteroaryl molecules of interest in their biological and physical properties.