Tris-decyl 15,21,39,45,63,69-hexahydroxy-16,20,40,44,64,68-hexamethylhexadecacyclo[57.13.3.311,25.335,49.14,8.128,32.152,56.012,17.019,24.036,41.043,48.060,65.066,74.067,72.018,82.042,78]tetraoctaconta-1(73),4(84),5,7,11(83),12(17),13,15,18,20,22,24,28,30,32(80),35(79),36(41),37,39,42,44,46,48,52(76),53,55,59,61,63,65,67(72),68,70,74,77,81-hexatriacontaen-2,9,26,33,50,57-hexayne-6,30,54-tricarboxylate | 860783-07-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: Tris-decyl 15,21,39,45,63,69-hexahydroxy-16,20,40,44,64,68-hexamethylhexadecacyclo[57.13.3.311,25.335,49.14,8.128,32.152,56.012,17.019,24.036,41.043,48.060,65.066,74.067,72.018,82.042,78]tetraoctaconta-1(73),4(84),5,7,11(83),12(17),13,15,18,20,22,24,28,30,32(80),35(79),36(41),37,39,42,44,46,48,52(76),53,55,59,61,63,65,67(72),68,70,74,77,81-hexatriacontaen-2,9,26,33,50,57-hexayne-6,30,54-tricarboxylate
• CAS: 860783-07-9
• 化学式: C₁₂₃H₁₁₄O₁₂
• 分子量: 1784.25
• InChiKey: CGPFOKJBHVHDNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  36.5
• 重原子数：
  135
• 可旋转键数：
  33
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  200
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Tris-decyl 15,21,39,45,63,69-hexahydroxy-16,20,40,44,64,68-hexamethylhexadecacyclo[57.13.3.311,25.335,49.14,8.128,32.152,56.012,17.019,24.036,41.043,48.060,65.066,74.067,72.018,82.042,78]tetraoctaconta-1(73),4(84),5,7,11(83),12(17),13,15,18,20,22,24,28,30,32(80),35(79),36(41),37,39,42,44,46,48,52(76),53,55,59,61,63,65,67(72),68,70,74,77,81-hexatriacontaen-2,9,26,33,50,57-hexayne-6,30,54-tricarboxylate 、 全氟丁基磺酰氟 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以80%的产率得到Tris-decyl 16,20,40,44,64,68-hexamethyl-15,21,39,45,63,69-hexakis(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyloxy)hexadecacyclo[57.13.3.311,25.335,49.14,8.128,32.152,56.012,17.019,24.036,41.043,48.060,65.066,74.067,72.018,82.042,78]tetraoctaconta-1(73),4(84),5,7,11(83),12(17),13,15,18,20,22,24,28,30,32(80),35(79),36(41),37,39,42,44,46,48,52(76),53,55,59,61,63,65,67(72),68,70,74,77,81-hexatriacontaen-2,9,26,33,50,57-hexayne-6,30,54-tricarboxylate
  参考文献：
  名称：

  Functionalized [3 + 3]Cycloalkynes:  Substituent Effect on Self-Aggregation by Nonplanar π−π Interactions

  摘要：

  Optically active (M)-2,11-dihydroxy-1,12-dimethylbenzolclphenanthrene-5,8-dicarbonitrile was synthesized from (M)-1,12-dimethyl-2,11-dinitrobenzo[c]phenanthrene-5,8-dicarbonitrile by the reduction and hydroxylation of nitro groups. The compound was converted to several oxygen-functionalized [3 + 3]cycloalkynes with -OH, -OSiMe2-t-Bu, -OAc, -OTf, or -ONf groups, which are chiral arylene ethynylene macrocycles containing three helicenes. The aggregation behaviors of these [3 + 3]cycloalkynes were examined in CHCl3, THF, and acetone using H-1 NMR, CD, and vapor pressure osmometry (VPO) studies and were compared with that of the parent [3 + 3]cycloalkyne. An increasing strength of aggregation in CHCl3 was observed in the following order of the substituted derivatives: -H > -ONf > -OTf > -OAc > -OSiMe2-t-Bu. In THF the following strength of aggregation was observed: -OTf > -ONf > -OAc > -H > -OSiMe2-t-Bu > -OH. The aggregation of the functionalized [3 + 3]cycloalkynes is stronger for the compounds with electron-withdrawing substituents than for those with electron-donating substituents. (M)-1,12-dimethylbenzo[c]phenanthrene-2,5,8,11-tetraol was also synthesized from the same intermediate. This electron-rich helicene was readily oxidized to 5,6-quinone in air, and the quinone was suggested to form a self-charge-transfer complex in solid state.

  DOI：

  10.1021/jo050732f
• 作为产物：
  描述：

  Tris-decyl 15,21,39,45,63,69-hexakis[[tert-butyl(dimethyl)silyl]oxy]-16,20,40,44,64,68-hexamethylhexadecacyclo[57.13.3.311,25.335,49.14,8.128,32.152,56.012,17.019,24.036,41.043,48.060,65.066,74.067,72.018,82.042,78]tetraoctaconta-1(73),4(84),5,7,11(83),12(17),13,15,18,20,22,24,28,30,32(80),35(79),36(41),37,39,42,44,46,48,52(76),53,55,59,61,63,65,67(72),68,70,74,77,81-hexatriacontaen-2,9,26,33,50,57-hexayne-6,30,54-tricarboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以97%的产率得到Tris-decyl 15,21,39,45,63,69-hexahydroxy-16,20,40,44,64,68-hexamethylhexadecacyclo[57.13.3.311,25.335,49.14,8.128,32.152,56.012,17.019,24.036,41.043,48.060,65.066,74.067,72.018,82.042,78]tetraoctaconta-1(73),4(84),5,7,11(83),12(17),13,15,18,20,22,24,28,30,32(80),35(79),36(41),37,39,42,44,46,48,52(76),53,55,59,61,63,65,67(72),68,70,74,77,81-hexatriacontaen-2,9,26,33,50,57-hexayne-6,30,54-tricarboxylate
  参考文献：
  名称：

  Functionalized [3 + 3]Cycloalkynes:  Substituent Effect on Self-Aggregation by Nonplanar π−π Interactions

  摘要：

  Optically active (M)-2,11-dihydroxy-1,12-dimethylbenzolclphenanthrene-5,8-dicarbonitrile was synthesized from (M)-1,12-dimethyl-2,11-dinitrobenzo[c]phenanthrene-5,8-dicarbonitrile by the reduction and hydroxylation of nitro groups. The compound was converted to several oxygen-functionalized [3 + 3]cycloalkynes with -OH, -OSiMe2-t-Bu, -OAc, -OTf, or -ONf groups, which are chiral arylene ethynylene macrocycles containing three helicenes. The aggregation behaviors of these [3 + 3]cycloalkynes were examined in CHCl3, THF, and acetone using H-1 NMR, CD, and vapor pressure osmometry (VPO) studies and were compared with that of the parent [3 + 3]cycloalkyne. An increasing strength of aggregation in CHCl3 was observed in the following order of the substituted derivatives: -H > -ONf > -OTf > -OAc > -OSiMe2-t-Bu. In THF the following strength of aggregation was observed: -OTf > -ONf > -OAc > -H > -OSiMe2-t-Bu > -OH. The aggregation of the functionalized [3 + 3]cycloalkynes is stronger for the compounds with electron-withdrawing substituents than for those with electron-donating substituents. (M)-1,12-dimethylbenzo[c]phenanthrene-2,5,8,11-tetraol was also synthesized from the same intermediate. This electron-rich helicene was readily oxidized to 5,6-quinone in air, and the quinone was suggested to form a self-charge-transfer complex in solid state.

  DOI：

  10.1021/jo050732f

文献信息

• Functionalized [3 + 3]Cycloalkynes:  Substituent Effect on Self-Aggregation by Nonplanar π−π Interactions
  作者：Hiroki Sugiura、Yusuke Takahira、Masahiko Yamaguchi

  DOI：10.1021/jo050732f

  日期：2005.7.1

  Optically active (M)-2,11-dihydroxy-1,12-dimethylbenzolclphenanthrene-5,8-dicarbonitrile was synthesized from (M)-1,12-dimethyl-2,11-dinitrobenzo[c]phenanthrene-5,8-dicarbonitrile by the reduction and hydroxylation of nitro groups. The compound was converted to several oxygen-functionalized [3 + 3]cycloalkynes with -OH, -OSiMe2-t-Bu, -OAc, -OTf, or -ONf groups, which are chiral arylene ethynylene macrocycles containing three helicenes. The aggregation behaviors of these [3 + 3]cycloalkynes were examined in CHCl3, THF, and acetone using H-1 NMR, CD, and vapor pressure osmometry (VPO) studies and were compared with that of the parent [3 + 3]cycloalkyne. An increasing strength of aggregation in CHCl3 was observed in the following order of the substituted derivatives: -H > -ONf > -OTf > -OAc > -OSiMe2-t-Bu. In THF the following strength of aggregation was observed: -OTf > -ONf > -OAc > -H > -OSiMe2-t-Bu > -OH. The aggregation of the functionalized [3 + 3]cycloalkynes is stronger for the compounds with electron-withdrawing substituents than for those with electron-donating substituents. (M)-1,12-dimethylbenzo[c]phenanthrene-2,5,8,11-tetraol was also synthesized from the same intermediate. This electron-rich helicene was readily oxidized to 5,6-quinone in air, and the quinone was suggested to form a self-charge-transfer complex in solid state.