1-溴-4-[2-(2-碘苯基)乙炔基]苯 | 832744-29-3

• 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-溴-4-[2-(2-碘苯基)乙炔基]苯
• 英文名称: 1-(4-bromophenyl)-2-(2-iodophenyl)ethyne
• 英文别名: 1-((4-bromophenyl)ethynyl)-2-iodobenzene；1‑((4‑bromophenyl)ethynyl)‑2‑iodobenzene；1-[(4-Bromophenyl)ethynyl]-2-iodobenzene；1-bromo-4-[2-(2-iodophenyl)ethynyl]benzene
• CAS: 832744-29-3
• 化学式: C₁₄H₈BrI
• 分子量: 383.026
• InChiKey: ZUAMUSAWWMTYCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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-溴-4-[2-(2-碘苯基)乙炔基]苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 indium(III) bromide 、 三乙胺 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (Z)-6-(bromo(4-bromophenyl)methylene)-5-(4-bromophenyl)-5,6-dihydropyrazolo[5,1-a]isoquinoline
  参考文献：
  名称：

  Synthesis of 5,6-Dihydropyrazolo[5,1-a]isoquinolines through Indium(III)-Promoted Halocyclizations of N-Propargylic Sulfonylhydrazones

  摘要：

  A novel method for the preparation of 5,6-dihydropyrazolo [5,1-a]isoquinoline via indium(III)-promoted halocyclizations of N-propargylic sulfonylhydrazones has been developed. The pyrazole and 3,4-dihydroisoquinoline moieties were synchronously formed via a cascade cyclization reaction using easily assembled open-chain compounds. The pyrazole and 3,4-dihydroisoquinoline moieties were formed via a cascade cyclization reaction using easily assembled open chain compounds.

  DOI：

  10.1021/acs.orglett.6b00534
• 作为产物：
  描述：

  2-碘苯甲基溴 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 1-溴-4-[2-(2-碘苯基)乙炔基]苯
  参考文献：
  名称：

  便利地合成二卤代二苯乙炔的双消除方案：量身定制的苯撑乙炔的多功能构建基块

  摘要：

  二卤代二苯基乙炔可通过β-取代的砜的双消除反应方便地合成，所述β-取代的砜容易从卤素取代的苄基砜和苯甲醛衍生物获得。仅通过选择起始化合物的芳环上卤素的取代位置，就可以在二苯乙炔骨架中的任何所需位置掺入卤素。由此获得的具有不同卤素取代基的二苯基乙炔由于卤素的不同反应性而经历了顺序的碳-碳键形成。因此，可以在任何位置的二苯基乙炔骨架上结合各种部分，从而可以设计各种具有调节的结构和组成的量身定制的亚苯基-亚乙炔基。

  DOI：

  10.1002/adsc.200404014

文献信息

• TBAI/TBHP-Mediated Cascade Cyclization toward Sulfonylated Indeno[1,2-<i>c</i>]quinolines
  作者：Jatuporn Meesin、Manat Pohmakotr、Vichai Reutrakul、Darunee Soorukram、Pawaret Leowanawat、Saowanit Saithong、Chutima Kuhakarn

  DOI：10.1021/acs.orglett.7b03246

  日期：2017.12.15

  aryldiyne derivatives with sulfonyl hydrazides in the presence of tetrabutylammonium iodide (TBAI) and tert-butyl hydroperoxide (TBHP) led to a cascade cyclization reaction to yield sulfonylated indeno[1,2-c]quinolines in moderate to good yields. The features of the methodology include metal-free reaction, the ease of reagent handling, and a broad functional group tolerance.

  的治疗邻-氨基取代的衍生物aryldiyne在四丁基碘化铵（TBAI）的存在和磺酰基酰肼叔丁基过氧化氢（TBHP）导致级联环化反应，得到磺酰基茚并[1,2- Ç〕喹啉在中度至良品率高。该方法的特点包括无金属反应，易于处理试剂和宽泛的官能团耐受性。
• Copper-catalysed three-component carboiodination of arynes: expeditious synthesis of<i>o</i>-alkynyl aryl iodides
  作者：Wenxuan Cao、Sheng-Li Niu、Li Shuai、Qing Xiao

  DOI：10.1039/c9cc09160b

  日期：——

  A copper-catalysed three-component iodoalkynylation reaction of arynes for the expeditious and versatile synthesis of o-alkynyl aryl iodides has been developed. Mechanism research shows that the reaction goes through two steps enabled by copper catalysis: the formation of 1-iodo-2-arylacetylene and the insertion of the aryne into a C(sp)-I bond.

  已开发了铜催化的芳烃三组分碘代炔基化反应，用于快速通用地合成邻炔基芳基碘化物。机理研究表明，该反应经历了铜催化实现的两个步骤：1-碘-2-芳基乙炔的形成以及芳烃插入C（sp）-I键中。
• Synthesis of tetracyclic chromenones via platinum(ii) chloride catalysed cascade cyclization of enediyne–enones
  作者：Mahalingam Sivaraman、Paramasivan T. Perumal

  DOI：10.1039/c3ob41911h

  日期：——

  PtCl2 catalysed cascade cyclization of an enediyne–enone system to afford a tetracyclic chromenone is reported, which proceeds through two consecutive highly regioselective 6-endo–dig cyclizations in a single step with the formation of two new C–C bonds and two new rings in excellent yield. A mechanism for this transformation is proposed based on the isolated intermediates.

  报道了 PtCl2 催化烯二炔烯酮体系级联环化生成四环色烯酮的过程，该过程一步完成两个连续的高区域选择性 6-endoâdig 环化，形成两个新的 CâC 键和两个新的环，收率极高。根据分离出的中间产物，提出了这种转化的机理。
• Double Elimination Protocol for Convenient Synthesis of Dihalodiphenylacetylenes: Versatile Building Blocks for Tailor-Made Phenylene-Ethynylenes
  作者：Akihiro Orita、Kazuhiko Miyamoto、Mikio Nakashima、Fangguo Ye、Junzo Otera

  DOI：10.1002/adsc.200404014

  日期：2004.6

  Dihalodiphenylacetylenes are conveniently synthesized by a double elimination reaction of β-substituted sulfones which are readily obtained from halogen-substituted benzyl sulfone and benzaldehyde derivatives. Halogens can be incorporated at any desired positions in the diphenylacetylene skeleton simply by choosing the substitution position of the halogen on the aromatic rings of the starting compounds

  二卤代二苯基乙炔可通过β-取代的砜的双消除反应方便地合成，所述β-取代的砜容易从卤素取代的苄基砜和苯甲醛衍生物获得。仅通过选择起始化合物的芳环上卤素的取代位置，就可以在二苯乙炔骨架中的任何所需位置掺入卤素。由此获得的具有不同卤素取代基的二苯基乙炔由于卤素的不同反应性而经历了顺序的碳-碳键形成。因此，可以在任何位置的二苯基乙炔骨架上结合各种部分，从而可以设计各种具有调节的结构和组成的量身定制的亚苯基-亚乙炔基。
• Synthesis of 5,6-Dihydropyrazolo[5,1-<i>a</i>]isoquinolines through Indium(III)-Promoted Halocyclizations of <i>N</i>-Propargylic Sulfonylhydrazones
  作者：Ren-Hao Li、Cheng-Ke Ding、Ya-Nan Jiang、Zong-Cang Ding、Xiao-Ming An、Hai-Tao Tang、Qi-Wei Jing、Zhuang-Ping Zhan

  DOI：10.1021/acs.orglett.6b00534

  日期：2016.4.1

  A novel method for the preparation of 5,6-dihydropyrazolo [5,1-a]isoquinoline via indium(III)-promoted halocyclizations of N-propargylic sulfonylhydrazones has been developed. The pyrazole and 3,4-dihydroisoquinoline moieties were synchronously formed via a cascade cyclization reaction using easily assembled open-chain compounds. The pyrazole and 3,4-dihydroisoquinoline moieties were formed via a cascade cyclization reaction using easily assembled open chain compounds.