1-(1'-naphthyl)-2-propyn-1-ol | 1791-23-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(1'-naphthyl)-2-propyn-1-ol
• 英文别名: 1-(naphthalen-1-yl)prop-2-yn-1-ol；1-naphthyl-2-propyn-1-ol；1-naphthalen-1-ylprop-2-yn-1-ol
• CAS: 1791-23-7
• 化学式: C₁₃H₁₀O
• 分子量: 182.222
• InChiKey: YQFFHWHTTIHIHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  1-(1'-naphthyl)-2-propyn-1-ol 在 4-二甲氨基吡啶 、 palladium on activated charcoal 、 氢气 、 silver nitrate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯苯 为溶剂， 反应 25.0h， 生成 1-(naphthalen-1-yl)-2-(1H-pyrazol-1-yl)propan-1-ol
  参考文献：
  名称：

  Silver(I)-Catalyzed Reaction between Pyrazole and Propargyl Acetates: Stereoselective Synthesis of the Scorpionate Ligands (E)-Allyl-gem-dipyrazoles (ADPs)

  摘要：

  The reaction between readily accessible pyrazole and propargyl acetates in the presence of Ag(I) catalyst yielded a new class of (E)-allyl-gem-dipyrazole scorpionate ligands: 1-aryl-2-N-pyrazolyl allyl acetates and 1,3-dipyrazolyl-3-arylpropene. The reaction showed broad substrate scope, and various functional and protecting groups were tolerated under the reaction conditions. The palladium(II) scorpionate complex could thus be easily prepared and successfully employed in Suzuki-Miyaura cross-couplings in water.

  DOI：

  10.1021/jo401867e
• 作为产物：
  描述：

  2-ethynyl-naphthalene-1-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以0.305 g的产率得到1-(1'-naphthyl)-2-propyn-1-ol
  参考文献：
  名称：

  [EN] ANTIPROLIFERATIVE BENZO [B] AZEPIN- 2 - ONES
  [FR] BENZO[B]AZÉPIN-2-ONES INHIBITRICES DE LA PROLIFÉRATION

  摘要：

  公开了公式(I)的化合物或其药物可接受的盐，其中W、X、Y、Z、R1、R2、R3和R4在本申请中有所描述，以及使用所述化合物治疗癌症的方法。

  公开号：

  WO2014009495A1

文献信息

• One-Pot Three-Component Catalytic Synthesis of Fully Substituted Pyrroles from Readily Available Propargylic Alcohols, 1,3-Dicarbonyl Compounds and Primary Amines
  作者：Victorio Cadierno、José Gimeno、Noel Nebra

  DOI：10.1002/chem.200701132

  日期：——

  preparation of fully substituted pyrroles, from readily accessible secondary propargylic alcohols, 1,3-dicarbonyl compounds and primary amines, has been developed. The one-pot multicomponent reaction, which is catalysed by the system [Ru(eta(3)-2-C(3)H(4)Me)(CO)(dppf)][SbF(6)]/CF(3)CO(2)H (dppf: 1,1'-bis(diphenylphosphanyl)ferrocene), involves initial propargylation of the 1,3-dicarbonyl compound promoted by

  已经开发了一种简单高效的方法，该方法可从容易获得的仲炔丙醇，1,3-二羰基化合物和伯胺制备完全取代的吡咯。一锅多组分反应，由系统[Ru（eta（3）-2-C（3）H（4）Me）（CO）（dppf）] [SbF（6）] / CF（3）催化）CO（2）H（dppf：1,1'-双（二苯基膦基）二茂铁），涉及CF（3）CO（2）H促进的1,3-二羰基化合物的初始炔丙基化，以及随后生成的γ之间的缩合-酮炔和伯胺得到炔丙基化的β-烯氨基酯或酮，将其进行钌催化的5-exo-dig环化反应，形成最终的吡咯。
• Cyclization Reaction of 4-Acyl-1-sulfonyl-1,2,3-triazoles Possessing Phenyl Rings through Generation of Electron-deficient Carbenoids
  作者：Qiang Zhao、Tomoya Miura、Masahiro Murakami

  DOI：10.1246/cl.190074

  日期：2019.6.5

  A rhodium-catalyzed cyclization reaction of 4-acyl-1-sulfonyl-1,2,3-triazoles possessing a phenyl ring is reported. Generated acceptor/acceptor carbenoids undergo cyclization by reacting either wit...

  报道了具有苯环的 4-酰基-1-磺酰基-1,2,3-三唑的铑催化环化反应。生成的受体/受体类卡宾通过与...
• Studies on Acetylenic Compounds. XXII. Ring Closure. (4). New Synthesis of Thiazoles and Imidazole.
  作者：Yasuo Yura

  DOI：10.1248/cpb.10.376

  日期：——

  It was found that the compounds having the general formula RCH(X)-C≡C-R'gave thiazole derivatives by reaction with thiourea. The relationship between the structure of thiazoles and substituent groups was clarified as follows : (1) When R=R'=Ph, 2-amino-4-benzyl-5-phenylthiazole (IId) is obtained, (2) When R=alkyl, R'=H, two kinds of thiazoles are obtained ; and (3) when R=R'=alkyl, thiazole derivative is not obtained. Similarly, propargyl bromide and phenylpropargyl bromide, when reacted with ammonium dithiocarbamate, afforded 2-mercapto-4-methylthiazole (XX) and 2-mercapto-4-benzylthiazole (XXIII), respectively. Further, 2-amino-4-methylimidazole (XXV) was obtained from guanidine and propargyl bromide.

  研究发现，具有通式RCH(X)-C≡C-R'的化合物在反应中与硫脲作用生成噻唑衍生物。噻唑结构和取代基之间的关系阐明如下：(1) 当R=R'=Ph时，获得2-氨基-4-苄基-5-苯基噻唑(IId)；(2) 当R=烷基，R'=H时，获得两种噻唑；(3) 当R=R'=烷基时，不生成噻唑衍生物。同样地，炔丙基溴和苯基炔丙基溴与氨荒酸盐反应，分别得到2-巯基-4-甲基噻唑(XX)和2-巯基-4-苄基噻唑(XXIII)。进一步地，从胍和炔丙基溴获得2-氨基-4-甲基咪唑(XXV)。
• Styrene as 4π-Component in Zn(II)-Catalyzed Intermolecular Diels–Alder/Ene Tandem Reaction
  作者：Min Zheng、Feng Wu、Kai Chen、Shifa Zhu

  DOI：10.1021/acs.orglett.6b01511

  日期：2016.8.5

  A mild Zn-catalyzed intermolecular Diels–Alder/ene tandem reaction with styrene as a 4π-component is reported. A variety of dihydronaphthalene products could be prepared in moderate to good yields. Moreover, a combination of DFT calculations and experiments was performed to further understand the mechanism of this unique tandem reaction.

  据报道，以苯乙烯为4π组分的轻度Zn催化的分子间Diels–Alder / ene串联反应。可以以中等到良好的产率制备各种二氢萘产物。此外，进行了DFT计算和实验的结合，以进一步了解这种独特的串联反应的机理。
• Phosphorous acid promoted isomerization of propargyl alcohols to α,β-unsaturated carbonyl compounds
  作者：Xiaotang Gan、Zuqi Fu、Lixin Liu、Yani Yan、Chao Chen、Yongbo Zhou、Jianyu Dong

  DOI：10.1016/j.tetlet.2019.06.065

  日期：2019.8

  A metal-free and two-phase protocol for the Meyer-Schuster isomerization of propargyl alcohols to the corresponding α,β-unsaturated carbonyl compounds has been achieved in the presence of stoichiometric phosphorous acid aqueous solution, which produces the desired products in high yields with excellent stereoselectivity. Compared with the traditional methods, the procedure features broad scope of the

  在化学计量的亚磷酸水溶液的存在下，已实现了炔丙醇Meyer-Schuster异构化为相应的α，β-不饱和羰基化合物的无金属两相方案，该方案可高收率地生产所需产物出色的立体选择性。与传统方法相比，该方法具有底物范围广，条件温和且易于分离的特点，是Meyer-Schuster反应的有吸引力的替代方法。