5'-phenyl-2,6,2'',6''-tetrakis(hydroxymethyl)-1,1':3',1''-terphenyl | 135990-04-4

• 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: 5'-phenyl-2,6,2'',6''-tetrakis(hydroxymethyl)-1,1':3',1''-terphenyl
• 英文别名: 5'-phenyl-2,6,2",6"-tetrakis(hydroxymethyl)-1,1':3',1"-terphenyl
• CAS: 135990-04-4
• 化学式: C₂₈H₂₆O₄
• 分子量: 426.512
• InChiKey: XYOSZZJWFNOBHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  80.92
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5'-phenyl-2,6,2'',6''-tetrakis(hydroxymethyl)-1,1':3',1''-terphenyl 在 吡啶 、 氢氧化钾 、 三溴化磷 作用下， 以 乙醇 、 苯 为溶剂， 反应 8.0h， 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
• 作为产物：
  描述：

  2,6-二甲基溴苯 在 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 sodium acetate 、 silver nitrate 、 magnesium 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 水 为溶剂， 反应 84.0h， 生成 5'-phenyl-2,6,2'',6''-tetrakis(hydroxymethyl)-1,1':3',1''-terphenyl
  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 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.