7-Tert-butyl-24,24-dioxo-17,31-dioxa-20,24lambda6,28-trithia-3,11-diazapentacyclo[30.2.2.213,16.15,9.022,26]nonatriaconta-1(35),5(39),6,8,13,15,22(26),32(36),33,37-decaene-4,10,18,30-tetrone | 381725-25-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 7-Tert-butyl-24,24-dioxo-17,31-dioxa-20,24lambda6,28-trithia-3,11-diazapentacyclo[30.2.2.213,16.15,9.022,26]nonatriaconta-1(35),5(39),6,8,13,15,22(26),32(36),33,37-decaene-4,10,18,30-tetrone
• 英文别名: 7-tert-butyl-24,24-dioxo-17,31-dioxa-20,24λ6,28-trithia-3,11-diazapentacyclo[30.2.2.213,16.15,9.022,26]nonatriaconta-1(35),5(39),6,8,13,15,22(26),32(36),33,37-decaene-4,10,18,30-tetrone
• CAS: 381725-25-3
• 化学式: C₃₆H₃₈N₂O₈S₃
• 分子量: 722.904
• InChiKey: ZSAPEDFOOHIUKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  49
• 可旋转键数：
  1
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  204
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  富马酸二乙酯 、 7-Tert-butyl-24,24-dioxo-17,31-dioxa-20,24lambda6,28-trithia-3,11-diazapentacyclo[30.2.2.213,16.15,9.022,26]nonatriaconta-1(35),5(39),6,8,13,15,22(26),32(36),33,37-decaene-4,10,18,30-tetrone 以 二甲基亚砜 、 邻二氯苯 为溶剂， 以84%的产率得到
  参考文献：
  名称：

  Change of Connectivity on Catenane Ring:  Ring Expansion by Annulation−Ring Scission Sequence

  摘要：

  [GRAPHICS]Ring expansion of a catenane without destruction of the interlocked structure was attained by Diels-Alder reaction followed by ozonolysis. Annulation by Diels-Alder reaction introduced a C4 fragment onto the ring, and the ozonolysis scissored the resulting double bond to expand the catenane ring. The annulation-ring scission sequence provides a general approach for changing the connectivity on a catenane ring without destroying the interlocked structure.

  DOI：

  10.1021/ol016586r
• 作为产物：
  描述：

  5-tert-butylisophthaloyl dichloride 在 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 18.0h， 生成 7-Tert-butyl-24,24-dioxo-17,31-dioxa-20,24lambda6,28-trithia-3,11-diazapentacyclo[30.2.2.213,16.15,9.022,26]nonatriaconta-1(35),5(39),6,8,13,15,22(26),32(36),33,37-decaene-4,10,18,30-tetrone
  参考文献：
  名称：

  Change of Connectivity on Catenane Ring:  Ring Expansion by Annulation−Ring Scission Sequence

  摘要：

  [GRAPHICS]Ring expansion of a catenane without destruction of the interlocked structure was attained by Diels-Alder reaction followed by ozonolysis. Annulation by Diels-Alder reaction introduced a C4 fragment onto the ring, and the ozonolysis scissored the resulting double bond to expand the catenane ring. The annulation-ring scission sequence provides a general approach for changing the connectivity on a catenane ring without destroying the interlocked structure.

  DOI：

  10.1021/ol016586r

文献信息

• Synthesis of [60]fullerene-functionalized rotaxanes
  作者：Hisahiro Sasabe、Kei-ichiro Ikeshita、G. Abraham Rajkumar、Nobuhiro Watanabe、Nobuhiro Kihara、Yoshio Furusho、Kazuhiko Mizuno、Akiya Ogawa、Toshikazu Takata

  DOI：10.1016/j.tet.2005.09.149

  日期：2006.2

  Synthesis of [60]fullerene (C60)-functionalized rotaxanes via Diels–Alder reactions with C60 is described. Diels–Alder reaction of C60 and sulfolene moiety as masked diene attached on the wheels of rotaxanes results in high yields of C60 incorporation. Rotaxanes are prepared by tin-catalyzed urethane-forming end-capping reaction with isocyanate of pseudorotaxane having the wheel carrying C60 functionality

  描述了通过Diels–Alder与C 60反应合成[60]富勒烯（C 60）-官能化轮烷的方法。Diels-C 60和环戊烷轮子上附着的被掩蔽的二烯所形成的亚砜部分的Diels-Alder反应导致C 60的掺入量很高。轮烷是通过锡催化氨基甲酸酯与端轮烷的异氰酸酯的端基封端反应而制备的，轮烷具有Diels-Alder反应引入的带有C 60官能度的轮子。Diels–Alder反应是通过C 60和假轮烷中带有端基的伪轮烷的端基反应（作为掩蔽的二烯）完成的。各种C 60这些Diels-Alder规程以中等到良好的收率制备了含[2]轮烷的化合物。
• Syntheses of [60]Fullerene and<i>N,N</i>-Bis(4-biphenyl)aniline-Tethered Rotaxane: Photoinduced Electron-Transfer Processes via Singlet and Triplet States of [60]Fullerene
  作者：Atula S. D. Sandanayaka、Kei-ichiro Ikeshita、Nobuhiro Watanabe、Yasuyuki Araki、Yoshio Furusho、Nobuhiro Kihara、Toshikazu Takata、Osamu Ito

  DOI：10.1246/bcsj.78.1008

  日期：2005.6

  A rotaxane containing [60]fullerene (C60) and N,N-bis(4-biphenyl)aniline (BBA) moieties was synthesized. In this structure, C60 acting as an electron acceptor, is attached to the crown-ether ring through which the axle with terminal BBA moieties acting as electron donors on both ends is penetrating. This rotaxane had a neutral amide moiety in the center of the axle in which two BBA moieties act as stoppers. The intra-rotaxane photoinduced electron-transfer processes of the C60 and BBA moieties were investigated by time-resolved transient absorption and fluorescence measurements while changing solvent polarity and temperature. Time-resolved transient absorption measurements of the rotaxanes confirmed that the long-lived charge-separated state (C60•−; BBA•+)rotaxane was formed via both the excited singlet and triplet states of C60 (1C60* and 3C60*, respectively) in polar solvents. The rate constants for charge-separation process were evaluated to be in the range of (3.6–3.7) × 108 s−1 via 1C60* and (5.1–5.6) × 107 s−1 via 3C60* in the ratio of (0.36–0.38):(0.43–0.51). The rate constants of charge recombination were 2.5 × 106 s−1 and 4.4 × 106 s−1, corresponding to the lifetimes of the charge-separated states of 400 ns and 230 ns in THF and benzonitrile, respectively. By the temperature dependences, the activation free-energy changes of charge-separation process via 3C60* were evaluated to be 0.10 eV, while those of the charge-recombination process were estimated to be 0.03 eV in THF and benzonitrile. These low activation energies are one of the characteristics of through-space electron transfer in the rotaxanes.

  我们合成了一种含有[60]富勒烯（C60）和 N,N-双（4-联苯）苯胺（BBA）分子的轮烷。在这种结构中，作为电子受体的 C60 连接到冠醚环上，而两端作为电子供体的末端 BBA 分子穿过冠醚环的轴。这种轮烷的轴中心有一个中性酰胺分子，其中两个 BBA 分子起阻挡作用。在改变溶剂极性和温度的情况下，通过时间分辨瞬态吸收和荧光测量，研究了 C60 和 BBA 分子在轮烷内部光诱导的电子转移过程。轮烷的时间分辨瞬态吸收测量结果证实，在极性溶剂中，长寿命电荷分离态（C60--; BBA-+）轮烷是通过 C60 的激发单线态和三线态（分别为 1C60* 和 3C60*）形成的。经评估，通过 1C60* 和 3C60* 电荷分离过程的速率常数分别为 (3.6-3.7) × 108 s-1 和 (5.1-5.6) × 107 s-1，其比例为 (0.36-0.38): (0.43-0.51)。电荷重组的速率常数分别为 2.5 × 106 s-1 和 4.4 × 106 s-1，对应于电荷分离态在 THF 和苯甲腈中的寿命分别为 400 ns 和 230 ns。根据温度相关性，通过 3C60* 进行电荷分离过程的活化自由能变化被估算为 0.10 eV，而在 THF 和苯甲腈中进行电荷重组过程的活化自由能变化被估算为 0.03 eV。这些低活化能是轮烷中通过空间电子转移的特征之一。
• Photoinduced Intrarotaxane Electron Transfer between Zinc Porphyrin and [60]Fullerene in Benzonitrile
  作者：Nobuhiro Watanabe、Nobuhiro Kihara、Yoshio Furusho、Toshikazu Takata、Yasuyuki Araki、Osamu Ito

  DOI：10.1002/anie.200390188

  日期：2003.2.10
• Bridged Polycatenane
  作者：Nobuhiro Watanabe、Yoshihiro Ikari、Nobuhiro Kihara、Toshikazu Takata

  DOI：10.1021/ma048782u

  日期：2004.9.1
• Change of Connectivity on Catenane Ring:  Ring Expansion by Annulation−Ring Scission Sequence
  作者：Nobuhiro Watanabe、Nobuhiro Kihara、Toshikazu Takata

  DOI：10.1021/ol016586r

  日期：2001.11.1

  [GRAPHICS]Ring expansion of a catenane without destruction of the interlocked structure was attained by Diels-Alder reaction followed by ozonolysis. Annulation by Diels-Alder reaction introduced a C4 fragment onto the ring, and the ozonolysis scissored the resulting double bond to expand the catenane ring. The annulation-ring scission sequence provides a general approach for changing the connectivity on a catenane ring without destroying the interlocked structure.