10,10-Dibenzyl-anthron | 5452-34-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 10,10-Dibenzyl-anthron
• 英文别名: 10,10-dibenzylanthrone；10,10-Dibenzylanthracen-9-one
• CAS: 5452-34-6
• 化学式: C₂₈H₂₂O
• 分子量: 374.482
• InChiKey: GDPNODKPUYAGCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  10,10-Dibenzyl-anthron 在 盐酸 、 溶剂黄146 、 锌 作用下， 生成 10,10,10'',10''-tetrabenzyl-10H,10''H-dispiro[anthracen-9,2'-oxiran-3',9''-anthracene]
  参考文献：
  名称：

  Barnett; Matthews, Journal of the Chemical Society, 1923, vol. 123, p. 390

  摘要：

  DOI：
• 作为产物：
  描述：

  9,9-Dibenzyl-9,10-dihydroanthracene 在 sodium dichromate 、 溶剂黄146 作用下， 反应 12.0h， 生成 10,10-Dibenzyl-anthron
  参考文献：
  名称：

  A convenient synthesis of 9,9-dialkyl-9,10-dihydroanthracenes and 10,10-dialkylanthrones: silicon-mediated regioselective dialkylation of 9,10-dihydroanthracene

  摘要：

  Described is a short and convenient approach to the synthesis of 9,9-dialkyl-9,10-dihydroanthracenes, 9,9,10-trialkyl-9,10-dihydroanthracenes, and 10,10-dialkylanthrones, some of which are otherwise unknown or inaccessible by conventional methods. Deprotonation of 9-(trimethylsilyl)-9,10-dihydroanthracene (2; 9-(trimethylsilyl)-9,10-DHA) followed by reaction with alkyl halides (RX) produces 9-alkyl-9-(trimethylsilyl)-9,10-DHAs 3-7 in 80-90% yields. Treatment of 3-7 with n-BuLi produces the 10-lithio derivatives that rearrange to 9-alkyl-9-lithio-10-(trimethylsilyl) intermediates; subsequent alkylation with RX generates 9,9-dialkyl-10-(trimethylsilyl)-9,10-DHAs 8-19. Formation of single stereoisomers 13-19 was suggested by NMR and confirmed in two cases, 15 and 16, by X-ray structure determination. The trimethylsilyl group is removed by tetra-butlyammonium fluoride (TBAF) to provide 9,9-dialkyl-9,10-DHAs 20-29 with impressive yields. Oxidation of either the 9,9-dialkyl-9,10-DHAs or 9,9-dialkyl-10-(trimethylsilyl)-9,10-DHAs with Cr(VI) oxidant furnished 10,10-dialkylanthrones 36-41 in 80-90% yields.

  DOI：

  10.1021/jo00036a029

文献信息

• Restricted Rotation Involving the Tetrahedral Carbon. XXXIII. Restricted Rotation about a C_sp³–C_sp²Bond in 10,10-Disubstituted 9-(2,6-Xylyl)-9,10-dihydroanthracene Derivatives
  作者：Mikio Nakamura、Michinori Oki

  DOI：10.1246/bcsj.53.2977

  日期：1980.10

  10-disubstituted 9-(2,6-xylyl)-9,10-dihydroanthracene derivatives have been prepared and their conformations and barriers to internal rotation about the Cxylyl–C9 bond have been examined. These compounds exist predominantly as a pseudo-equatorial form in the ground state for rotation. A large effect is inserted by the substituents in 10 position on barriers to rotation and is interpreted in terms of a rotation-inversion

  已经制备了一系列 10,10-二取代的 9-(2,6-二甲苯基)-9,10-二氢蒽衍生物，并研究了它们的构象和围绕 Cxylyl-C9 键的内部旋转障碍。这些化合物主要以旋转基态的伪赤道形式存在。在旋转障碍上的 10 位取代基插入了一个很大的影响，并根据旋转反转机制而不是甲基交换过程的简单旋转机制来解释，这是通过 1H NMR 光谱观察到的。在具有两个全氯基团和 9 位羟基的化合物中发现了最高的旋转障碍。高势垒归因于过渡态的不稳定，其中 9-芳基采用轴向构象，由于三个带负电的基团被迫在相当近的区域平行排列。因此，当存在周围氯时，9-OH 变为 9-H 会降低旋转障碍，而...
• Acid-Catalyzed Cyclization of Anthracenol Derivatives to Homotriptycenes
  作者：Chunmei Gao、Derong Cao、Sheyang Xu、Herbert Meier

  DOI：10.1021/jo0526791

  日期：2006.4.1

  quantitative yields. Since the starting compounds are easily accessible from 9(10H)-anthracenone, this process represents the most facile route to such pentacyclic systems. An electron-releasing methoxy group enables the intramolecular electrophilic substitution in its para position. In the absence of such an activation, a number of alternative processes can occur, namely the acid-catalyzed dehydration to anthracene

  在苯环中具有高电子密度的10-苄基-9,10-二氢蒽基-9-ols在酸存在下以几乎定量的产率显示出与相应的同三联体的环过环的闭合。由于起始化合物很容易从9（10 H）-蒽酮获得，因此该方法代表了通往此类五环系统的最简便方法。释放电子的甲氧基能够在其对位进行分子内亲电取代。在没有这种活化的情况下，会发生许多替代过程，即酸催化脱水成蒽衍生物，其中（R≠H）或不进行（R = H）重排或仲醇歧化成相应的酮和碳氢化合物。
• PHOTOCHROMIC SPIROPYRANS, AND COMPOSITIONS AND ARTICLES CONTAINING SAME
  申请人：——

  公开号：US20020049341A1

  公开（公告）日：2002-04-25

  Novel spiropyran compounds, particularly with photochromic properties, are disclosed, as well as photochromic compositions and ophthalmic articles (e.g. lenses) containing said compounds. The photochromes have been designed so as to have a high colorability, a high sensitivity to activating radiation breaking the pyran ring, to be entirely or practically free from coloration in a non activated (non exposed) state, to have an intense coloration following activation and a high coverage of the visible spectrum in combination with at least one other photochrome, and to have high rates of coloration/decoloration. The spiropyrans are easily produced and photochemically stable, and are, e.g., of formula (i), wherein L=(a);(b).

  本发明涉及新颖的螺环吡喃化合物，特别是具有光致变色性质的化合物，以及含有该化合物的光致变色组合物和眼科制品（例如镜片）。这些光致变色剂被设计为具有高染色性、对破坏吡喃环的激活辐射敏感、在未被激活（未暴露）状态下完全或几乎不染色、在激活后具有强烈的染色和与至少一种其他光致变色剂相结合的可见光谱高覆盖率，以及高染色/脱色速率。这些螺环吡喃化合物易于生产和光化学稳定，例如式（i）其中L=（a）;（b）。
• Photochemistry and photophysics of ketyl radicals containing the anthrone moiety
  作者：J. C. Netto-Ferreira、W. F. Murphy、R. W. Redmond、J. C. Scaiano

  DOI：10.1021/ja00167a053

  日期：1990.5

  employed to produce the corresponding ketyl radicals 1-4 by photoreduction in the presence of suitable hydrogen donors. The excited-state behavior of these radicals has been examined with use of two-laser, two-color techniques. The lifetimes for the excited ketyl radicals, ranging from 7.9 ns for 3 to 33 ns for 2, are longer than that observed for benzophenone ketyl, thus suggesting that conformational

  几种含有蒽酮部分的酮的光化学已被用于在合适的氢供体存在下通过光还原产生相应的羰基自由基 1-4。已经使用双激光、双色技术检查了这些自由基的激发态行为。激发的 ketyl 自由基的寿命从 3 的 7.9 ns 到 2 的 33 ns，比观察到的二苯甲酮 ketyl 长，因此表明构象限制在控制激发的自由基寿命方面起着关键作用。在 3 的情况下，主要的衰变模式涉及从 10 位失去一个苄基，而对于 1 和 2，该过程涉及从羟基位置失去一个氢原子；在 2 的情况下，这已被拉曼光谱证实。
• 一种芳香化链转移试剂及其制备方法
  申请人：北京大学

  公开号：CN114656340B

  公开（公告）日：2023-03-21

  本发明提供一种芳香化链转移试剂及其制备方法，具体为提供一种具有自由基加成碎裂化链转移活性的9,9‑二苄基‑10‑亚甲基‑9,10‑二氢蒽类化合物及其制备方法；本发明的9,9‑二苄基‑10‑亚甲基‑9,10‑二氢蒽类化合物具有二苯乙烯骨架从而具有相当高的自由基加成活性，其芳构化的碎裂化途径则为其提供了较高的碎裂化驱动力；该类化合物添加进口腔树脂材料中时，可在不明显改变力学性质和双键转化率的情况下，显著降低聚合收缩应力。