2'-bromo-2,6,2'',6''-tetrakis(bromomethyl)-1,1':3',1''-terphenyl | 124602-44-4

• 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: 2'-bromo-2,6,2'',6''-tetrakis(bromomethyl)-1,1':3',1''-terphenyl
• 英文别名: 1,3-bis[2,6-bis(bromomethyl)phenyl]-2-bromobenzene
• CAS: 124602-44-4
• 化学式: C₂₂H₁₇Br₅
• 分子量: 680.897
• InChiKey: FMZDUDBYUQPDGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.36
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  2'-bromo-2,6,2'',6''-tetrakis(bromomethyl)-1,1':3',1''-terphenyl 在 氢氧化钾 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 反应 6.0h， 生成 13H,15H-1,19-(methanothiomethano<1,3>-benzenomethanothiomethano)-8,12:20,24-dimetheno-5H,7H-dibenzo<1,9>dithiacycloeicosin
  参考文献：
  名称：

  Synthesis of cuppedophanes and cappedophanes. Two new classes of cyclophanes with molecular cavities

  摘要：

  DOI：

  10.1021/jo00290a017
• 作为产物：
  描述：

  2'-bromo-2,6,2'',6''-tetramethyl-1,1':3',1''-terphenyl 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 sodium acetate 、 三溴化磷 、 silver nitrate 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 苯 为溶剂， 反应 82.0h， 生成 2'-bromo-2,6,2'',6''-tetrakis(bromomethyl)-1,1':3',1''-terphenyl
  参考文献：
  名称：

  Synthesis of cuppedophanes and cappedophanes. Two new classes of cyclophanes with molecular cavities

  摘要：

  DOI：

  10.1021/jo00290a017

文献信息

• Synthesis of self-filled, vaulted, and intracavity functionalized cappedophanes
  作者：Thottumkara K. Vinod、Harold Hart

  DOI：10.1021/jo00019a032

  日期：1991.9

  Two approaches to the synthesis of vaulted cappedophanes 3v are described. In the first, the walls and ceiling were prefabricated as in tetrathiol 5 (10a and 10b, Scheme II, are specific examples), which was then coupled with a m-terphenyl tetrabromide such as 4. This route was most successful when the m-terphenyl base carried a large substituent (Ph, Br) in the 5' position. Thus tetrathiol 10a and tetrabromide 25 gave vaulted cappedophane 27v in good yield (Scheme VIII). In the absence of a 5' substituent, the major product was the self-filled conformer. For example, 10a and 4 gave mainly 11sf (62%) and only 2% of its vaulted conformer 11v (Scheme III), and tetrathiol 10b reacted with 4 to give (79%) only the self-filled conformer 15sf (Scheme IV). In the second approach, a cuppedophane with suitably functionalized walls was first constructed, and the cap was attached in a second step. For example, bisphenol 29, when coupled with p-xylylene dibromide, gave mainly vaulted conformer 11v (51%) and only a trace of 11sf (Scheme IX). Extension of this method to several other dihalides, however, gave mainly self-filled conformers (Schemes XI and XII) and even p-xylylene dibromide gave only self-filled product 33sf when the bisphenol contained a substituent at C2' of the m-terphenyl base (Scheme XIII). The reasons for the predominant formation of self-filled vis-a-vis vaulted cappedophane conformers are discussed. These studies open the way for the synthesis of vaulted cappedophanes containing functionality within the molecular cavity.