3-phenylhex-1-yn-3-ol | 141946-99-8

• 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: 3-phenylhex-1-yn-3-ol
• CAS: 141946-99-8
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: YVJDQQIGAUTHII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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-phenylhex-1-yn-3-ol 在 H₂O*H₂K₂O₂ 、 乙炔 作用下， 以 二甲基亚砜 为溶剂， 以70%的产率得到2,4-diethyl-3-methyl-7-methylene-1,5-diphenyl-6,8-dioxabicyclo[3.2.1]octane
  参考文献：
  名称：

  A peculiar transition-metal-free cyclodimerization of propargylic alcohols to vinyl bicyclic ketals

  摘要：

  Propargylic alcohols, alkylaryl(hetaryl)ethynyl carbinols, under transition-metal-free conditions (KOH/DMSO, 70-80 degrees C, 10-15 min) unexpectedly undergo stereoselective cyclodimerization to 7-methylene-6,8-dioxabicyclo[3.2.1]octanes having the scaffold of known insect pheromones and marine toxins. Under acetylenic pressure the yields of bicyclic ketals reach 80%. In all the cases, the cyclodimers are formed exclusively as one diastereomer. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.050
• 作为产物：
  描述：

  苯丁酮 、 乙炔 在 乙醇 、 potassium hydroxide semihydrate 作用下， 以 二甲基亚砜 为溶剂， 15.0 ℃ 、101.33 kPa 条件下， 反应 1.5h， 以68%的产率得到3-phenylhex-1-yn-3-ol
  参考文献：
  名称：

  Improved synthesis of tertiary propargyl alcohols by the Favorskii reaction of alkyl aryl (hetaryl) ketones with acetylene

  摘要：

  Alkyl aryl (hetaryl) ketones react with acetylene under atmospheric pressure in the superbasic system KOH-EtOH-H2O-DMSO at 10-15A degrees C (2 h) to give the corresponding tertiary propargyl alcohols in up to 91% yield. The procedure requires no large excess of KOH and low-boiling inflammable solvents, produces few wastes, and is safe and convenient on the laboratory scale; there are no limitations for its large-scale application. DOI: 10.1134/S1070428013010028

  DOI：

  10.1134/s1070428013010028

文献信息

• Transition metal-free ether coupling and hydroamidation enabling the efficient synthesis of congested heterocycles
  作者：Goki Hirata、Yusuke Shimoharai、Taisei Shimada、Takashi Nishikata

  DOI：10.1039/d1cc06871g

  日期：——

  The transition-metal-free synthesis of sterically congested ethers and heterocycles via the stereospecific etherification and hydroamidation of α-bromocarboxamides and alkynols.

  通过α-溴代羧酰胺和炔醇的立体特异性醚化和羟基化，实现了立体阻碍醚和杂环的过渡金属自由合成。
• Amine-Release Annulation of Enaminones: Bimetallic Co-Catalytic Synthesis of Cyclopentadienes from Alkynes
  作者：Kai Chen、Jie Lv、Jie Chen、Jian Zhang、Ling Li、Min Zhao、Yaojia Jiang

  DOI：10.1021/acs.orglett.3c01568

  日期：2023.6.30

  An efficient Au(III)/Ag(I) co-catalytic platform has been established for the synthesis of cyclopentadienes through amine-release annulation of enaminones with alkynes. Vinylcarbenoids that were generated from 1,2-migration of propargyl esters may undergo a tandem annulation process with enaminones to give aminocyclopentenes as key intermediates. The bimetal catalytic system is compatible with a broad

  建立了一个高效的 Au(III)/Ag(I) 共催化平台，用于通过烯胺酮与炔烃的胺释放成环合成环戊二烯。由炔丙酯的 1,2-迁移产生的乙烯基类胡萝卜素可以与烯胺酮进行串联环化过程，得到氨基环戊烯作为关键中间体。双金属催化体系在温和的反应条件下与广泛的底物范围兼容。获得的环戊二烯可以进行后期修饰，形成具有高化学和区域选择性的复杂分子。
• Platinum Catalysed Hydrostannylation of Terminal Alkynes; Highly Selective Synthesis of Vinyl Stannanes
  作者：Dean D. Roberts、Mark G. McLaughlin

  DOI：10.1002/adsc.202300379

  日期：2023.5.23

  β-(E)-vinyl stannane. The catalyst system is able to provide the corresponding vinyl stannane in selectivities which surpasses that which is typically afforded under palladium catalysis. Additionally, a telescoped hydrometallation/cross-coupling sequence has been developed, allowing for application of the vinyl stannanes without excessive manipulation or purification of the intermediate stannane.

  我们首次研究了铂络合物在末端炔烃氢化锡基化中的应用。筛选了一系列铂络合物，事实证明 PtCl 2 /XPhos 为 β-(E)-乙烯基锡烷提供了最佳选择性。该催化剂体系能够以超过通常在钯催化下提供的选择性提供相应的乙烯基锡烷。此外，还开发了一种伸缩式加氢金属化/交叉偶联序列，允许在不过度操作或纯化中间体锡烷的情况下应用乙烯基锡烷。
• Photoinduced Regioselective Fluorination and Vinylation of Remote C(sp³)–H Bonds Using Thianthrenium Salts
  作者：Mengqi Luo、Shibo Zhu、Chao Yang、Lin Guo、Wujiong Xia

  DOI：10.1021/acs.orglett.4c01420

  日期：2024.5.24

  fluorinated alkene synthesis using easily accessible and modular thianthrenium salts with electron-withdrawing alkynes or propargyl alcohols is reported. Vinyl radical intermediates, formed by the reaction between the alkyl or trifluoromethyl thianthrenium salts and electronically diverse alkynes, can mediate the key 1,5-HAT process of regioselective C(sp3)–H fluorination and vinylation. This protocol

  本文报道了一种光氧化还原驱动的氟化烯烃合成实用方案，该方案使用易于获得和模块化的铊盐与吸电子炔烃或炔丙醇进行合成。乙烯基自由基中间体由烷基或三氟甲基噻烯​​盐与电子多样化的炔烃反应形成，可以介导区域选择性 C(sp 3 )–H 氟化和乙烯基化的关键 1,5-HAT 过程。该协议提供了在温和光催化条件下以 21-79% 的产率和广泛的底物范围直接获得结构多样的三氟甲基或远端氟官能化烯烃产品的途径。
• O'Hagan, David; Zaidi, Naveed A., Journal of the Chemical Society. Perkin transactions I, 1992, # 8, p. 947 - 949
  作者：O'Hagan, David、Zaidi, Naveed A.

  DOI：——

  日期：——