1-乙炔基-2-(戊-1-炔-1-基)苯 | 731857-18-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-乙炔基-2-(戊-1-炔-1-基)苯
• 英文名称: 1-ethynyl-2-(pent-1-yn-1-yl)benzene
• 英文别名: 1-ethynyl-2-(pent-1-ynyl)benzene；1-Ethynyl-2-pent-1-ynylbenzene
• CAS: 731857-18-4
• 化学式: C₁₃H₁₂
• 分子量: 168.238
• InChiKey: ZSSAMXQHPPGFIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  65 °C(Press: 0.2 Torr)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-乙炔基-2-(戊-1-炔-1-基)苯 在 platinum(II) chloride 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以48%的产率得到2,3-二氢-1H-苯并[e]茚
  参考文献：
  名称：

  通过链状烷烃的CH键插入，铂催化二烯炔的芳构化。

  摘要：

  PtCl 2（5mol％）是通过链状烷烃的CH键插入而使烯二炔芳构化的有效催化剂。提出该环化的反应机理涉及铂-π-炔烃中间体。这种环化不仅适用于末端炔烃，而且适用于内部炔烃。

  DOI：

  10.1021/ol052962m
• 作为产物：
  描述：

  1-bromo-2-(pent-1-ynyl)benzene 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 copper(l) iodide 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 72.5h， 生成 1-乙炔基-2-(戊-1-炔-1-基)苯
  参考文献：
  名称：

  Syntheses of Syn and Anti Doublebent [5]Phenylene

  摘要：

  [GRAPHICS]The parent and dipropyl-substituted anti (1a,b) and syn doublebent (2a,b) [5]phenylenes have been assembled by CpCo-catalyzed double cyclization of regiospecifically constructed appropriate hexaynes. H-1 NMR, NICS, and an X-ray structural analysis of is reflect the aromatizing effect of double angular fusion on the central ring of the linear [3]phenylene substructure.

  DOI：

  10.1021/ol049225v

文献信息

• Ruthenium-Catalyzed Aromatization of Enediynes via Highly Regioselective Nucleophilic Additions on a π-Alkyne Functionality. A Useful Method for the Synthesis of Functionalized Benzene Derivatives
  作者：Arjan Odedra、Chang-Jung Wu、Taduri Bhanu Pratap、Chun-Wei Huang、Ying-Fen Ran、Rai-Shung Liu

  DOI：10.1021/ja043047j

  日期：2005.3.1

  TpRu(PPh3)(CH3CN)2 PF6 (10 mol %) catalyst effected the nucleophilic addition of water, alcohols, aniline, acetylacetone, pyrroles, and dimethyl malonate to unfunctionalized enediynes under suitable conditions (100 degrees C, 12-24 h) and gave functionalized benzene products in good yields. In this novel cyclization, nucleophiles very regioselectively attack the internal C1' alkyne carbon of enediynes

  TpRu(PPh3)(CH3CN)2 PF6 (10 mol %) 催化剂在合适的条件下（100 摄氏度，12-24 小时）实现了水、醇、苯胺、乙酰丙酮、吡咯和丙二酸二甲酯与未官能化的烯二炔的亲核加成和以良好的收率得到官能化苯产物。在这种新颖的环化中，亲核试剂非常区域选择性地攻击烯二炔的内部 C1' 炔烃碳，得到苯衍生物作为单一区域异构体。使用甲氧基取代基的实验排除了萘基阳离子作为反应中间体参与（邻乙炔基苯基）炔烃环化的可能。氘标记实验表明催化活性物质是钌-π-炔烃而不是钌-亚乙烯基物质。o-(2' -碘乙炔基）苯基炔烃与醇。我们在一系列实验的基础上提出了这种亲核芳构化的亲核加成/插入机制。
• Gold(I)-Catalyzed Regioselective Inter-/Intramolecular Addition Cascade of Di- and Triynes for Direct Construction of Substituted Naphthalenes
  作者：Saori Naoe、Yamato Suzuki、Kimio Hirano、Yusuke Inaba、Shinya Oishi、Nobutaka Fujii、Hiroaki Ohno

  DOI：10.1021/jo300771f

  日期：2012.6.1

  intermolecular addition–intramolecular carbocyclization reaction of dialkynylbenzenes was developed. In this reaction, regioselective addition of an external nucleophile toward the terminal alkyne and subsequent 6-endo-dig cyclization proceeded to give the 1,3-disubstituted naphthalenes in good yields. The direct synthesis of disubstituted chrysenes via a gold-catalyzed addition and double cyclization cascade

  开发了金催化的二炔基苯的级联分子间加成-分子内碳环化反应。在该反应中，进行了向末端炔烃的区域亲核试剂的区域选择性加成和随后的6 -endo-dig环化，从而以良好的产率得到了1，3-二取代的萘。还实现了通过使用三炔类底物的金催化加成和双环化级联反应直接合成二取代的chrysenes。
• Gold-Catalyzed Three-Component Annulation: Efficient Synthesis of Highly Functionalized Dihydropyrazoles from Alkynes, Hydrazines, and Aldehydes or Ketones
  作者：Yamato Suzuki、Saori Naoe、Shinya Oishi、Nobutaka Fujii、Hiroaki Ohno

  DOI：10.1021/ol203072u

  日期：2012.1.6

  Polysubstituted dihydropyrazoles were directly obtained by a gold-catalyzed three-component annulation. This reaction consists of a Mannich-type coupling of alkynes with N,N′-disubstituted hydrazines and aldehydes/ketones followed by intramolecular hydroamination. Cascade cyclization using 1,2-dialkynylbenzene derivatives as the alkyne component was also performed producing fused tricyclic dihydropyrazoles

  多取代的二氢吡唑是通过金催化的三组分环合法直接获得的。该反应由炔与N，N′-二取代的肼和醛/酮的曼尼希型偶联，然后进行分子内加氢胺化组成。还进行了使用1,2-二炔基苯衍生物作为炔烃组分的级联环化反应，以高收率生产了稠合的三环二氢吡唑。
• An Intramolecular Reaction between Pyrroles and Alkynes Leads to Pyrrole Dearomatization under Cooperative Actions of a Gold Catalyst and Isoxazole Cocatalysts
  作者：Satish Bhausaheb Dawange、Rai-Shung Liu

  DOI：10.1021/acs.orglett.4c02601

  日期：2024.8.30

  The gold-catalyzed one-pot synthesis of 3H-benzo[e]isoindoles (3) from a mixture of isoxazole (2) and diynamides (1) is described. This tandem catalysis involves two separate steps: (i) initial synthesis of 2-(3-pyrrolyl)-1-alkynylbenzenes and (ii) a novel alkyne/pyrrole coupling reaction through pyrrole dearomatization. Our control experiments reveal the cooperative action of the gold catalyst and

  描述了由异恶唑( 2 )和二炔酰胺( 1 )的混合物金催化一锅法合成3H-苯并[ e ]异吲哚( 3 )。这种串联催化涉及两个独立的步骤：（i）2-（3-吡咯基）-1-炔基苯的初始合成和（ii）通过吡咯脱芳构化的新型炔/吡咯偶联反应。我们的对照实验揭示了金催化剂和异恶唑助催化剂的协同作用，使新型炔/吡咯偶联能够导致 1,2-酰基转移。
• Gold(I)-Catalyzed Polycyclizations of Polyenyne-Type Anilines Based on Hydroamination and Consecutive Hydroarylation Cascade
  作者：Kimio Hirano、Yusuke Inaba、Kiyosei Takasu、Shinya Oishi、Yoshiji Takemoto、Nobutaka Fujii、Hiroaki Ohno

  DOI：10.1021/jo2018119

  日期：2011.11.4

  A hydroamination-double hydroarylation cascade using aniline derivatives bearing a trienyne moiety as the substrate was efficiently promoted by a gold(I) catalyst to produce benzo[a]naphtho [2,1-c]carbazole derivatives in good yields. This reaction is applicable to various substituted trienyne-type anilines, including 2,3-diethynylthiophene derivatives. The reaction of anilines bearing a tetraenyne and pentaenyne moiety allows direct construction of highly fused carbazoles by tetra- and pentacyclization, respectively, through hydroamination and consecutive hydroarylation without producing any theoretical waste products from the substrates.