1-phenyl-3-ethoxypropyne | 27975-60-6

• 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: 1-phenyl-3-ethoxypropyne
• 英文别名: ethyl 3-phenyl-2-propynyl ether；(3-ethoxyprop-1-yn-1-yl)benzene；1-Phenyl-3-ethoxypropin；Ethyl-(3-phenyl-2-propin-1-yl)ether；1-Ethoxy-3-phenyl-prop-2-in；3-Ethoxyprop-1-ynylbenzene
• CAS: 27975-60-6
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: ACXLHZKVVCFAGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-phenyl-3-ethoxypropyne 在 triethyloxonium fluoroborate 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 pentacarbonyl{1-ethoxy-3-phenyl-3-(phenylamino)-(Z)-2-propenylidene}chromium
  参考文献：
  名称：

  炔基菲舍尔羧甲基苯作为通过β-氨基氮二烯生产二氟二氮杂硼硼烷配合物的平台

  摘要：

  研究了β-氨基-1-氮杂二烯支架中Cr（0）的β-氨基-α，β-不饱和Fischer卡宾的反应性。这些被β-给体基团官能化的配合物经历了以铜催化剂为主要中间体的金属转移过程，从而提示了可能的反应机理。所获得的氮杂二烯被用于二氟二氮杂硼烷酮的合成，其被寻找为荧光材料。

  DOI：

  10.1002/ejoc.201901047
• 作为产物：
  描述：

  3-苯基-2-丙炔-1-胺 盐酸盐 在 吡啶 、 sodium hydroxide 、 nitrosonium tetrafluoroborate 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-phenyl-3-ethoxypropyne
  参考文献：
  名称：

  Carbene-Carbene Interconversion between 1- and 3-Phenyl-2-propynylidenes

  摘要：

  1-Phenyl-3-diazopropyne (Id) and 3-phenyl-3-diazopropyne (2d) were prepared and photolyzed under various conditions. In ethanol at ambient temperatures, both 1d and 2d gave a 1:10 +/- 1 mixture of 1-phenyl-3-ethoxypropyne (3) and 3-phenyl-3-ethoxypropyne (4). The photolyses of matrix-isolated 1d and 2d at cryogenic temperatures were followed by EPR, IR, and UV-visible spectroscopy. EPR experiments in 2-methyltetrahydrofuran (MTHF), isopentane, and ethanol-d(6) matrices at 9 K showed spectra due to a mixture of the corresponding triplet carbenes 1c (\D/hc\ = 0.543 and \E/hc\ = 0.003 cm(-1)) and 2c (\D/hc\ = 0.526 and \E/hc\ = 0.010 cm(-1)). The ratio of the generated carbenes carried the memory of the starting diazo compounds; 1c and 2c were produced mainly from 1d and 2d, respectively. Carbene 2c isomerized to 1c at 70-90 K in MTHF and ethanol-d(6) and at 44-68 K in isopentane, indicating that 1c was thermodynamically more stable than 2c on the triplet ground-state potential energy surface. IR and UV-visible absorption experiments employing various media (argon, isopentane, N-2, CO/Ar, O-2/N-2, and O-2/Ar) revealed that the photolysis of 2d afforded mostly absorptions due to 2c. Photolysis of 1d produced similar spectra, due mainly to 2c, together with weak absorptions due to 1c. The different results observed in EPR and IR experiments were explained by the difference in the matrices in which the diazo groups were photolyzed. Calculations at the ab initio MP2/DZV(d) level of theory showed that the triplet ground state of 1c was more thermodynamically stable than 2c by 1.41 kcal/mol, in agreement with the experimental results. The situation is reversed in the singlet manifold, where 2c was computed to be much lower in energy than 1c. The energy differences (Delta E(ST)) between the singlet and triplet states were computed to be 15.7 and 11.0 kcal/mol for 1c and 2c, respectively, with the DZV(d) basis set.

  DOI：

  10.1021/ja00093a017

文献信息

• Nickel-Catalyzed Highly Chemo-, Regio-, and Stereoselective Three-Component Reaction of Norbornene with Two Alkynes
  作者：Kenichi Ogata、Jun Sugasawa、Yuka Atsuumi、Shin-ichi Fukuzawa

  DOI：10.1021/ol9025556

  日期：2010.1.1

  The first three-component reaction of norbornene with two alkynes leading to 1,5-enyne via C−H bond activation of terminal silylacetylene was achieved using a Ni(cod)2/phosphine catalyst. This reaction is applicable for various internal alkynes and norbornene derivatives with high regio- and stereoselectivities.

  使用Ni（cod）2 /膦催化剂实现了降冰片烯与两个炔烃的第一个三组分反应，通过末端甲硅烷基乙炔的CH键活化反应生成1,5-炔烃。该反应适用于具有高区域和立体选择性的各种内部炔烃和降冰片烯衍生物。
• Copper-Catalyzed Hydroxyl-Directed Aminoarylation of Alkynes
  作者：Jiaqiong Sun、Guangfan Zheng、Tao Xiong、Qiao Zhang、Jinbo Zhao、Yan Li、Qian Zhang

  DOI：10.1021/acscatal.6b00759

  日期：2016.6.3

  A facile, copper-catalyzed aminoarylation reaction of various aryl/alkyl alkynes was realized by utilizing N-fluoroarylsulfonimides (NFSI) as aminoarylation or amination reagent with hydroxyl as directing group. With this methodology, various α,β-unsaturated carbonyl compounds and indenones were efficiently constructed, and the synthetic application for indole derivatives was also provided. The aminoarylation

  利用N-氟芳基磺酰亚胺（NFSI）作为氨基芳基化或胺化试剂，以羟基为导向基团，实现了各种芳基/烷基炔烃的简便的铜催化的氨基芳基化反应。利用该方法，可以有效地构建各种α，β-不饱和羰基化合物和茚满，并提供了吲哚衍生物的合成应用。氨基芳基化反应是通过在C-C三键/ C-乙烯基-C芳基键的形成过程中将铜配位的氮自由基区域特异性加成来进行的，随后进行其他一系列自由基过程。
• Highly Chemoselective Nickel-Catalyzed Three-Component Cross-Trimerization of Three Distinct Alkynes Leading to 1,3-Dien-5-ynes
  作者：Kenichi Ogata、Jun Sugasawa、Shin-ichi Fukuzawa

  DOI：10.1002/anie.200902099

  日期：2009.8.3

  Cross‐yned: The first highly chemoselective three‐component cross‐trimerization between a triisopropylsilylacetylene, an ether‐functionalized unsymmetrical internal alkyne, and a symmetrical internal alkyne leading to a 1,3‐dien‐5‐yne was achieved using a [Ni(cod)2]/PPh3 catalyst. This reaction is applicable for various internal alkynes with high regio‐ and stereoselectivities.

  交叉式：使用[Ni（ cod）2 ] / PPh 3催化剂。该反应适用于具有高区域和立体选择性的各种内部炔烃。
• [EN] QUINOLINONE LYSYL OXIDASE-LIKE 2 INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS QUINOLINONE DE LA LYSYL OXYDASE-LIKE 2 ET UTILISATIONS DESDITS INHIBITEURS
  申请人：PHARMAKEA INC

  公开号：WO2017139274A1

  公开（公告）日：2017-08-17

  Described herein are compounds that are LOXL2 inhibitors, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders associated with LOXL2 activity.

  本文描述了一些具有LOXL2抑制剂作用的化合物，制备这些化合物的方法，包含这些化合物的药物组合物和药物，以及使用这些化合物治疗与LOXL2活性相关的疾病、病症或障碍的方法。
• Catalyst-Free Trans-Selective Oxyiodination and Oxychlorination of Alkynes Employing N–X (Halogen) Reagents
  作者：Jiaqiong Sun、Yunliang Guo、Jiuli Xia、Guangfan Zheng、Qian Zhang

  DOI：10.3390/molecules28217420

  日期：——

  β-halogenated enol esters and ethers are versatile building blocks in organic synthesis, which has attracted increasing attention. In this study, we report the facile trans-oxyiodination and oxychlorination of alkynes, leading to the direct construction of versatile halogenated enol esters and ethers. This transformation features an easy operation, optimal atomic economy, a strong functional group

  β-卤代烯醇酯和醚是有机合成中的通用结构单元，引起了越来越多的关注。在这项研究中，我们报道了炔烃的简单反式氧化碘化和氧氯化，从而直接构建了多功能的卤代烯醇酯和醚。该转化具有操作简单、原子经济性好、官能团耐受性强、底物范围广、反式选择性优异等特点。采用高亲电子双功能 N-X（卤素）试剂是实现广泛反应通用性的关键。据我们所知，这种转变代表了第一个采用 N-X（卤素）试剂作为氧化源和卤化源的卤氧化系统。