N-(2-((4-chlorophenyl)ethynyl)phenyl)benzamide | 1612876-08-0

• 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: N-(2-((4-chlorophenyl)ethynyl)phenyl)benzamide
• CAS: 1612876-08-0
• 化学式: C₂₁H₁₄ClNO
• 分子量: 331.801
• InChiKey: NBHPKCUVSDSTCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  二苯基二硒醚 、 N-(2-((4-chlorophenyl)ethynyl)phenyl)benzamide 在 iron(III) chloride 、 ammonium acetate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  氯化铁/三有机二硒化物促进邻炔基丙二胺的区域和立体选择性环化：( Z）-4-（硫属元素）亚甲基苯并恶嗪的合成

  摘要：

  AbstractIntramolecular 6‐exo‐dig cyclization of ortho‐alkynylanilides has been employed in a regio‐ and stereoselective synthesis of (Z)‐4‐(chalcogen)methylenebenzoxazines. Several reaction parameters were screened for the efficient cyclization of ortho‐alkynylanilides. Among them, the reaction of ortho‐alkynylanilides (0.25 mmol) with iron(III) chloride (3.0 equiv.) and diorganyl diselenides (0.75 equiv.) in dichloromethane as solvent gave the products in acceptable to good yields. The resulting products were then subjected to a nitrogen–oxygen exchange reaction with ammonium acetate to furnish quinazoline derivatives. The one‐pot version of this cyclization, starting directly from 2‐alkynylanilines, avoiding the previous preparation of ortho‐alkynylanilides was also briefly studied.magnified image

  DOI：

  10.1002/adsc.201300925

文献信息

• Palladium-catalyzed highly regioselective 6-exo-dig cyclization and alkenylation of ortho-ethynylanilides: the synthesis of polyene-substituted benzo[d][1,3]oxazines
  作者：Zhong-Jian Cai、Chao Yang、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1039/c5cc06510k

  日期：——

  A Pd-catalyzed highly regioselective 6-exo-dig cyclization/alkenylation reaction of ortho-ethynylanilides has been developed.

  一种钯催化的高区域选择性6-exo-dig环化/烯基化反应已经被开发出来，用于ortho-乙炔基苯胺。
• Synthesis of Tribenzo[<i>b</i>,<i>e</i>,<i>g</i>]phosphindole Oxides via Radical Bicyclization Cascades of <i>o</i>-Arylalkynylanilines
  作者：Jie Li、Wen-Wen Zhang、Xiao-Jing Wei、Wen-Juan Hao、Guigen Li、Shu-Jiang Tu、Bo Jiang

  DOI：10.1021/acs.orglett.7b02071

  日期：2017.9.1

  oxides has been developed, enabling dual C(sp2)–H functionalization along with the cleavage of the C–N bond. The combination between regioselective P-centered radical-triggered [3 + 2] cyclization and C-centered radical-induced cross-coupling in a one-pot manner delivered 27 examples of tribenzo[b,e,g]phosphindole oxides with generally high regioselectivity. A reasonable mechanism for forming such products

  已开发出一种新的DTBP / Mg（NO 3）2介导的邻芳基炔基苯胺与仲芳基膦氧化物的双环化级联反应，使双C（sp 2）-H官能化以及C-N键的裂解成为可能。区域选择性的P中心自由基触发的[3 + 2]环化与C中心的自由基诱导的交叉耦合的一锅法相结合，提供了27个通常具有较高区域选择性的三苯并[ b，e，g ]磷吲哚氧化物实例。提出了形成这种涉及自由基加成-环化级联反应的产物的合理机理。