N,N-tetramethylene-N'-(2-iodophenyl)triazene | 214628-08-7

• 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,N-tetramethylene-N'-(2-iodophenyl)triazene
• 英文别名: 2-[2-[4-(2-Iodophenyl)buta-1,3-diynyl]phenyl]ethynyl-tri(propan-2-yl)silane
• CAS: 214628-08-7
• 化学式: C₂₇H₂₉ISi
• 分子量: 508.517
• InChiKey: WESGNTQHXHNZGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.26
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  N,N-tetramethylene-N'-(2-iodophenyl)triazene 在 bis-triphenylphosphine-palladium(II) chloride 、 氢氧化钾 、 copper(l) iodide 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 、 水 、 三乙胺 为溶剂， 反应 0.5h， 生成 C₃₂H₁₄
  参考文献：
  名称：

  A versatile synthetic route to dehydrobenzoannulenes via in situ generation of reactive alkynes

  摘要：

  This paper outlines the development of a protocol that allows in situ generation of unstable alkynes under Pd-catalyzed cross-coupling conditions. Cu-mediated intramolecular cyclization of the resultant alpha,omega -polyynes provides dehydrobenzoannulenes as singular species, in very good overall yields, and in a variety of topologies that are inaccessible by traditional routes or previously available in low yield only. In addition, we will discuss the solid-state structure and reactivity of these macrocycles, as well as the ability of the planar dehydrobenzoannulenes to support weak induced ring currents. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00229-0
• 作为产物：
  描述：

  N,N-tetramethylene-N'-(2'-iodophenyl)triazene 在 bis-triphenylphosphine-palladium(II) chloride 、 氢氧化钾 、 copper(l) iodide 、 碘甲烷 作用下， 以 四氢呋喃 、 水 、 三乙胺 为溶剂， 生成 N,N-tetramethylene-N'-(2-iodophenyl)triazene
  参考文献：
  名称：

  A versatile synthetic route to dehydrobenzoannulenes via in situ generation of reactive alkynes

  摘要：

  This paper outlines the development of a protocol that allows in situ generation of unstable alkynes under Pd-catalyzed cross-coupling conditions. Cu-mediated intramolecular cyclization of the resultant alpha,omega -polyynes provides dehydrobenzoannulenes as singular species, in very good overall yields, and in a variety of topologies that are inaccessible by traditional routes or previously available in low yield only. In addition, we will discuss the solid-state structure and reactivity of these macrocycles, as well as the ability of the planar dehydrobenzoannulenes to support weak induced ring currents. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00229-0

文献信息

• Synthesis and Spectroscopic Studies of Expanded Planar Dehydrotribenzo[n]annulenes Containing One or Two Isolated Alkene Units
  作者：W. Brad Wan、Ryan C. Chiechi、Timothy J. R. Weakley、Michael M. Haley

  DOI：10.1002/1099-0690(200109)2001:18<3485::aid-ejoc3485>3.0.co;2-i

  日期：2001.9

  cross-coupling with an intramolecular cyclization strategy. 1H NMR studies of these macrocycles and comparison with related systems verify that highly alkynylated dehydrobenzoannulenes possess weak induced ring currents, indicative of aromatic (4n+2 π-systems) and anti-aromatic (4n π-systems) behavior, in spite of their large size and extensive benzannulation.

  通过将原位 Pd/Cu 介导的交叉偶联与分子内环化策略相结合，合成了含有分离的烯烃键的脱氢苯并环烯衍生物。这些大环的 1H NMR 研究以及与相关系统的比较证实，高度炔化的脱氢苯并环烯具有弱的感应环电流，表明芳香族（4n+2 π 系统）和反芳香族（4n π 系统）行为，尽管它们很大大小和广泛的苯环化。
• Synthesis of expanded planar dehydrobenzoannulenes: Weakly diatropic, weakly paratropic, or atropic?
  作者：W.Brad Wan、David B. Kimball、Michael M. Haley

  DOI：10.1016/s0040-4039(98)01583-4

  日期：1998.9

  Use of a Cu/Pd cross-coupling strategy has led to the synthesis of the first dehydrobenzoannulenes containing triacetylenic linkages. NMR studies of these macrocycles and comparison with other known systems indicate that, in spite of their large size and extensive benzannelation, dehydrobenzoannulenes possess weak induced ring currents. (C) 1998 Elsevier Science Ltd. All rights reserved.
• A versatile synthetic route to dehydrobenzoannulenes via in situ generation of reactive alkynes
  作者：Michael L Bell、Ryan C Chiechi、Charles A Johnson、David B Kimball、Adam J Matzger、W Brad Wan、Timothy J.R Weakley、Michael M Haley

  DOI：10.1016/s0040-4020(01)00229-0

  日期：2001.4

  This paper outlines the development of a protocol that allows in situ generation of unstable alkynes under Pd-catalyzed cross-coupling conditions. Cu-mediated intramolecular cyclization of the resultant alpha,omega -polyynes provides dehydrobenzoannulenes as singular species, in very good overall yields, and in a variety of topologies that are inaccessible by traditional routes or previously available in low yield only. In addition, we will discuss the solid-state structure and reactivity of these macrocycles, as well as the ability of the planar dehydrobenzoannulenes to support weak induced ring currents. (C) 2001 Elsevier Science Ltd. All rights reserved.