9,10,9',10'-tetrahydro-9,9'-biacridyl | 4838-42-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9,10,9',10'-tetrahydro-9,9'-biacridyl
• 英文别名: 9,10,9',10'-tetrahydro-[9,9']biacridinyl；9,9'-Biacridan；9-(9,10-dihydroacridin-9-yl)-9,10-dihydroacridine
• CAS: 4838-42-0
• 化学式: C₂₆H₂₀N₂
• 分子量: 360.458
• InChiKey: PWBKDZWODDXCDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9,10,9',10'-tetrahydro-9,9'-biacridyl 在 硫酸 作用下， 生成 吖啶 、 2,2'-dianilino-bibenzyl-α,α'-diol
  参考文献：
  名称：

  Lehmstedt; Hundertmark, Chemische Berichte, 1930, vol. 63, p. 1229

  摘要：

  DOI：
• 作为产物：
  描述：

  吖啶 在 丙泊酚 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以52%的产率得到9,10,9',10'-tetrahydro-9,9'-biacridyl
  参考文献：
  名称：

  CIDEP机械探测吖啶存在下受阻酚的新型光化学偶联

  摘要：

  在作为光吸收剂的吖啶存在下受阻酚的辐照得到双酚和联吖啶。CIDEP 研究建立了三联体吖啶提取氢的途径。总体机制由产品分析和 CIDEP 研究提出。

  DOI：

  10.1246/cl.1995.845

文献信息

• Photodecarboxylation of unmodified carboxylic acids with use of aza aromatic compounds
  作者：Keiji Okada、Katsura Okubo、Masaji Oda

  DOI：10.1016/s0040-4039(00)70663-0

  日期：——

  A very simple procedure for photodecarboxylation of intact carboxylic acids leading to alkanes is developed with use of aza aromatic compounds as light absorbers and t-BuSH as a hydrogen donor.

  通过使用氮杂芳族化合物作为光吸收剂和使用t-BuSH作为氢供体，开发了一种非常简单的方法，将完整的羧酸光脱羧生成烷烃。
• Stoichiometrically Sensitized Decarboxylation Occurring in the Two-Component Molecular Crystals of Aza Aromatic Compounds and Aralkyl Carboxylic Acids
  作者：Hideko Koshima、Kuiling Ding、Yosuke Chisaka、Teruo Matsuura、Ikuko Miyahara、Ken Hirotsu

  DOI：10.1021/ja971156a

  日期：1997.10.1

  crystals of aralkyl carboxylic acids such as 3-indolepropionic acid (a) and 1-naphthylacetic acid (b) combined with acridine (1) or phenanthridine (2) as an electron acceptor. The 1:1 hydrogen bonded crystals were prepared by recrystallization from the solutions. Irradiation of the crystals at −70 °C caused highly selective decarboxylation to give corresponding decarboxylated compounds alone in nearly

  通过利用一系列芳烷基羧酸如 3-吲哚丙酸 (a) 和 1-萘基乙酸 (b) 与吖啶 (1) 或菲啶 (2) 结合的双组分分子晶体，可以实现高度选择性的光脱羧反应。电子受体。通过从溶液中重结晶制备 1:1 氢键晶体。由于晶格中自由基物质的热运动较小，在 -70 °C 下对晶体进行辐照会导致高度选择性脱羧，从而以几乎定量的产率单独得到相应的脱羧化合物。在照射晶体时，通过从酸到 1 或 2 的电子转移以及随后的质子转移和脱羧作用产生羧酸根和氢吖啶或氢菲啶自由基。
• Photochemical Reductive Acylation and Oxidative Acyl Activation on Phenazine and Related Nitrogen Heterocycles
  作者：Makoto Takagi、Setsuo Goto、Tsutomu Matsuda

  DOI：10.1246/bcsj.53.1777

  日期：1980.6

  Irradiation of phenazine in acetaldehyde or propionaldehyde solution gave an N-acylated 5,10-dihydrophenazine. Acridine similarly gave 9-acyl-9,10-dihydroacridine, and 10-methylacridinium salt gave 9-acyl-10-methyl-9,10-dihydroacridine. In methanol N-acylated dihydro-phenazines reacted with N-bromosuccinimide to give phenazine and methyl car boxy lates in quantitative yield.

  在乙醛或丙醛溶液中辐照吩嗪得到 N-酰化的 5,10-二氢吩嗪。吖啶类似地得到9-酰基-9,10-二氢吖啶，10-甲基吖啶盐得到9-酰基-10-甲基-9,10-二氢吖啶。在甲醇中，N-酰化二氢吩嗪与 N-溴代琥珀酰亚胺反应以定量收率得到吩嗪和甲基羧酸酯。
• Solid-State Photoreaction in Two-Component Molecular Crystals of Thienylacetic Acids and Aza Aromatic Compounds
  作者：Hideko Koshima、Daisuke Matsushige、Masashi Miyauchi、Junko Fujita

  DOI：10.1016/s0040-4020(00)00506-8

  日期：2000.9

  two-component molecular crystals of 2-thienylacetic acid (1) or bis(2-thienyl)acetic acid (2) with aza aromatic compounds such as acridine (a) and phenanthridine (b) were prepared by crystallization from the solutions of both components. Irradiation of the crystals caused photodecarboxylation and radical intermediates which give decarboxylated and condensation products. The relationship between the crystal

  通过从溶液中结晶，制备了一系列2-噻吩基乙酸（1）或双（2-噻吩基）乙酸（2）与氮杂芳族化合物（如（啶（a）和菲啶（b））的两组分分子晶体。这两个组成部分。晶体的照射引起光脱羧和自由基中间体，这些中间体产生脱羧和缩合产物。讨论了晶体结构与反应路径之间的关系。
• Photoreactivities of two kinds of bimolecular crystals formed from acridine and phenothiazine
  作者：Hideko Koshima、Yang Wang、Teruo Matsuura、Ikuko Miyahara、Hisashi Mizutani、Ken Hirotsu、Tsuyoshi Asahi、Hiroshi Masuhara

  DOI：10.1039/a701221g

  日期：——

  A yellow crystal 3 and a red crystal 4 simultaneously crystallize from a solution of acridine 1 and phenothiazine 2 in acetonitrile. Similar N · · · H–N hydrogen bonding pairs of 1 and 2 are formed in the two crystals. The 3∶4 crystal 3 has a slightly uncommon molecular arrangement of which four acridine molecules out of twelve are disordered in the unit cell. The 1∶1 crystal 4 has a more rigid packing of the hydrogen bonding pairs. Irradiation of 3 gives a photoadduct 5 as the sole product, whereas 4 shows almost no photoreactivity. The occurrence of photoinduced electron transfer has been confirmed by the measurement of transient absorption spectra of the crystals 3 and 4. However, the two-stage decay of the transient absorption of 3 with lifetimes of 2 and 50 ps is different from that of 4 with a single short lifetime of 2 ps. Upon irradiating 3, electron transfer, proton transfer and subsequent radical coupling occur over the shortest distance of 4.1 Å between the preradical carbon and nitrogen atoms in the crystal lattice followed by dehydrogenation to afford the product 5. In the case of the red crystal 4, the radical coupling is difficult because of the longer coupling distance of 5.6 Å and the more restricted movement in the rigid crystal lattice. The results indicate that the observed photochemical behaviour of 3 and 4 are controlled by the molecular arrangement in the crystal lattice.

  黄色晶体3和红色晶体4同时从吖啶1和吩噻嗪2的乙腈溶液中结晶出来。类似的 N · · · H-N 氢键对 1 和 2 在两个晶体中形成。 3:4晶体3的分子排列有点不常见，其中12个吖啶分子中的4个在晶胞中是无序的。 1:1晶体4具有更刚性的氢键对堆积。 3 的照射产生光加合物 5 作为唯一产物，而 4 几乎没有显示出光反应性。晶体3和4的瞬态吸收光谱的测量证实了光致电子转移的发生。然而，寿命分别为2和50 ps的3的瞬态吸收的两级衰减与寿命为2和50 ps的4的瞬态吸收的两阶段衰减不同。单个寿命较短，为 2 ps。照射 3 后，晶格中自由基前碳原子和氮原子之间最短距离 4.1 Å 内发生电子转移、质子转移和随后的自由基偶联，然后脱氢得到产物 5。在红色晶体 4 的情况下，由于 5.6 Å 的较长耦合距离以及刚性晶格中的运动受到更多限制，自由基耦合很困难。结果表明，观察到的3和4的光化学行为是由晶格中的分子排列控制的。