2,6,2'',6''-tetrakis(bromomethyl)-1,1':3',1''-terphenyl | 116129-61-4

• 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: 2,6,2'',6''-tetrakis(bromomethyl)-1,1':3',1''-terphenyl
• 英文别名: 1,1':3',1''-Terphenyl, 2,2'',6,6''-tetrakis(bromomethyl)-；2-[3-[2,6-bis(bromomethyl)phenyl]phenyl]-1,3-bis(bromomethyl)benzene
• CAS: 116129-61-4
• 化学式: C₂₂H₁₈Br₄
• 分子量: 602.001
• InChiKey: JLXQRMVKTNNZDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2903999090

反应信息

• 作为反应物：
  描述：

  1,2,4,5-tetrakis(mercaptomethyl)benzene 、 2,6,2'',6''-tetrakis(bromomethyl)-1,1':3',1''-terphenyl 在 氢氧化钾 作用下， 以 乙醇 、 苯 为溶剂， 以16%的产率得到7,12-dihydro-14H-1,9:10,18-bis(methanothiomethano)-19,23-metheno-5H-tribenzo<1,6>-dithiacycloheptadecin
  参考文献：
  名称：

  Cupped-and capophanes，两类新的具有分子腔的化合物

  摘要：

  合成这些 du m-phenylene [2.2] 2 metacyclophane et de m, p, o-phenylene [2] 3 metacyclophanes

  DOI：

  10.1021/ja00227a054
• 作为产物：
  描述：

  tetramethylterphenyl 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 以27%的产率得到2,6,2'',6''-tetrakis(bromomethyl)-1,1':3',1''-terphenyl
  参考文献：
  名称：

  Synthesis of novel lantern-shaped molecules based on resorcin[4]arene and m-terphenyl units

  摘要：

  Novel lantern-shaped molecules with a large enclosure were synthesized by taking advantage of resorcin[4]arene and m-terphenyl units as the capping and bottom fragments, respectively. Two conformers with different cavity volume were obtained selectively by changing the substituent on the bottom unit.

  DOI：

  10.1016/0040-4039(95)01610-t

文献信息

• The First Electrochemically Active Cuppedophanes:  Bis(tetrathiafulvalene)cuppedophanes
  作者：Jan Oskar Jeppesen、Kazuo Takimiya、Jan Becher

  DOI：10.1021/ol000138m

  日期：2000.8.1

  The synthesis of the first tetrathiafulvalene-containing cuppedophanes is reported, together with conformational study of the structures by (1)H NMR spectroscopy. The bis(TTF)cuppedophane 6 represents a novel type of cuppedophane.

  报道了第一种含四硫富瓦烯的铜蝶烷的合成，以及通过（1）H NMR光谱对结构进行构象研究。bis（TTF）cuppedophane 6代表一种新型的cuppedophane。
• Synthesis of two noninterconvertible conformers of a single host. Self-filled and vaulted cappedophanes
  作者：Thottumkara K. Vinod、Harold Hart

  DOI：10.1021/ja00164a077

  日期：1990.4

  La synthese de deux conformeres de l'α-methyl m-phenylene p-phenylenedioxy tetrathia [3 4 ] metacyclophane est effectuee a partir de l'acetate de dibromo-3,5 phenyle, de tetrakis-mercaptomethyl terphenyle et de bis-bromomethyl-1,4 benzene

  La 合成 de deux conformeres de l'α-methyl m-phenylene p-phenylenedioxy tetrathia [3 4 ] metacyclophane est effectuee a partir de l'acetate de dibromo-3,5 phenyle, de tetrakis-mercaptomethyl terphenyle et de bis-bromomethyl- 1,4苯
• 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.
• Synthesis of cuppedophanes and cappedophanes. Two new classes of cyclophanes with molecular cavities
  作者：Thottumkara Vinod、Harold Hart

  DOI：10.1021/jo00290a017

  日期：1990.2
• Reduction of DMAD-anthracene adducts. Synthesis and conformations of substituted cyclodecadienes
  作者：Ashok Anantanarayan、Harold Hart

  DOI：10.1021/jo00003a019

  日期：1991.2

  A general method for reducing DMAD-anthracene adducts to the corresponding enediols is described. Thus, the ester groups of 1 were reduced without C = C reduction using the DIBAH-nBuLi ''ate'' complex to give previously unknown 2 in high yield. Analogous enediols 5-7 were similarly prepared. Base treatment of dibromide 3 and dithiol 9, both prepared from 2 by standard methods, gave conformationally rigid dithiacyclodecadiene 10. With o-, m-, and p-xylylenedithiols, dibromide 3 gave respectively the conformationally labile cyclophanes 12 and 13 and the rigid cyclophane 14. Tetrabromide 16 and dithiol 9 gave cuppedophane 17, but tetrabromide 18 and 9 formed bis-m-cyclophane 19 instead.