10,33-dihydroxy-25-bromo-13H,15H-1,19-(methanothiomethano<1,3>benzenomethanothiomethano)-8,12:20,24-dimetheno-5H,7H-dibenzo<1,9>dithiacycloeicosin | 135990-11-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 10,33-dihydroxy-25-bromo-13H,15H-1,19-(methanothiomethano<1,3>benzenomethanothiomethano)-8,12:20,24-dimetheno-5H,7H-dibenzo<1,9>dithiacycloeicosin
• 英文别名: 40-bromo-3,11,19,27-tetrathiaheptacyclo[15.15.7.15,9.121,25.134,38.013,39.029,33]dotetraconta-1(33),5(42),6,8,13(39),14,16,21,23,25(41),29,31,34(40),35,37-pentadecaene-7,23-diol
• CAS: 135990-11-3
• 化学式: C₃₈H₃₃BrO₂S₄
• 分子量: 729.847
• InChiKey: YGYLTEMTOKRYOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.55
• 重原子数：
  45.0
• 可旋转键数：
  0.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,4-二(溴甲基)苯 、 10,33-dihydroxy-25-bromo-13H,15H-1,19-(methanothiomethano<1,3>benzenomethanothiomethano)-8,12:20,24-dimetheno-5H,7H-dibenzo<1,9>dithiacycloeicosin 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以47%的产率得到
  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：

  在 氢氧化钾 、 乙二胺 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 苯 为溶剂， 反应 8.0h， 生成 10,33-dihydroxy-25-bromo-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 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