28-phenyl-4,11-dioxa-18,38,43,47-tetrathianonacyclo[22.17.3.314,32.26,9.13,40.112,16.126,30.020,25.031,36]dopentaconta-1,3(45),6(52),7,9(51),12,14,16(50),20,22,24,26,28,30(49),31(36),32,34,40-octadecaene | 126790-20-3

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 28-phenyl-4,11-dioxa-18,38,43,47-tetrathianonacyclo[22.17.3.314,32.26,9.13,40.112,16.126,30.020,25.031,36]dopentaconta-1,3(45),6(52),7,9(51),12,14,16(50),20,22,24,26,28,30(49),31(36),32,34,40-octadecaene
• CAS: 126790-20-3
• 化学式: C₅₂H₄₄O₂S₄
• 分子量: 829.184
• InChiKey: DAKOCZHBTYQITR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.52
• 重原子数：
  58.0
• 可旋转键数：
  1.0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2,4,6-溴碘苯 在 吡啶 、 氢氧化钾 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 sodium acetate 、 三溴化磷 、 silver nitrate 、 magnesium 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙醇 、 水 、 苯 为溶剂， 反应 92.0h， 生成 28-phenyl-4,11-dioxa-18,38,43,47-tetrathianonacyclo[22.17.3.314,32.26,9.13,40.112,16.126,30.020,25.031,36]dopentaconta-1,3(45),6(52),7,9(51),12,14,16(50),20,22,24,26,28,30(49),31(36),32,34,40-octadecaene
  参考文献：
  名称：

  Synthesis of self-filled, vaulted, and intracavity functionalized cappedophanes

  摘要：

  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.

  DOI：

  10.1021/jo00019a032

文献信息

• 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