10,10-dioxo-10λ⁶-thioxanthen-9-ol | 10445-85-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻喃类
• 英文名称: 10,10-dioxo-10λ⁶-thioxanthen-9-ol
• 英文别名: 10,10-dioxo-9H-thioxanthen-9-ol
• CAS: 10445-85-9
• 化学式: C₁₃H₁₀O₃S
• 分子量: 246.287
• InChiKey: WZGGHJXZYQKKSV-UHFFFAOYSA-N

物化性质

• 熔点：
  185-186 °C
• 沸点：
  468.5±24.0 °C(Predicted)
• 密度：
  1.451±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10,10-dioxo-10λ⁶-thioxanthen-9-ol 生成 bis-(10,10-dioxo-10λ⁶-thioxanthen-9-yl)-ether
  参考文献：
  名称：

  The Two-Step Reduction--Oxidation of Thiaxanthone-5-dioxide and Thiaxanthenol-5-dioxide

  摘要：

  DOI：

  10.1021/ja01169a067
• 作为产物：
  描述：

  10,10-二氧代噻吨-9-酮 在 溶剂黄146 、 锌 作用下， 生成 10,10-dioxo-10λ⁶-thioxanthen-9-ol
  参考文献：
  名称：

  Fehnel, Journal of the American Chemical Society, 1949, vol. 71, p. 1063,1066

  摘要：

  DOI：

文献信息

• Tandem O–H Insertion/[1,3]-Alkyl Shift of Rhodium Azavinyl Carbenoids with Benzylic Alcohols: A Route To Convert C–OH Bonds into C–C Bonds
  作者：Pengbing Mi、Rapolu Kiran Kumar、Peiqiu Liao、Xihe Bi

  DOI：10.1021/acs.orglett.6b02459

  日期：2016.10.7

  Alcohols are among the most abundant and commonly used organic feedstock in industrial processes and academic research. The first tandem O–H insertion/[1,3]-alkyl shift reaction reported is between benzylic alcohols and rhodium azavinyl carbenoids derived from N-sulfonyl-1,2,3-triazoles, which provides a strategically novel way of cleaving C–OH bonds and forming C–C bonds. The substrate scope is broad

  酒精是工业过程和学术研究中最丰富，最常用的有机原料之一。报道的第一个串联的O–H插入/ [1,3]-烷基转移反应是在苄醇与衍生自N-磺酰基-1,2,3-三唑的氮杂氮杂乙烯基铑类化合物之间进行的，这提供了一种策略性地裂解C-的新方法。 OH键并形成C–C键。底物的范围很广，能够覆盖1°-，2°-和3°-苄醇。而且，它构成了构造α-氨基酮的新的有力的合成方法。机理研究表明，氧鎓叶立德的[1,3]-烷基移位是C-OH键断裂的原因。
• A Metallomicellar Catalyst for Controlled Oxidation of Alcohols and Lignin Mimics in Water using Open Air as Oxidant
  作者：Prabaharan Thiruvengetam、Pragyansmruti Sunani、Dillip Kumar Chand

  DOI：10.1002/cssc.202301754

  日期：——

  Alcohol groups and β‐O‐4 (C−C) linkages are widespread in biomass feedstock that are abundant renewable resource for value‐added chemicals. The development of sustainable protocols for direct oxidation or oxidative cleavage of feedstock materials in a controlled fashion, using open air as an oxidant is an intellectually stimulating task to produce industrially important value‐added carbonyls. Further, the oxidative depolymerization of lignin into fine chemicals has evoked interest in recent times. Herein, we report the first example of a catalyst system that could activate molecular oxygen from atmospheric air for controlled oxidation and oxidative cleavage/depolymerization of feedstock materials such as alcohols, β‐O‐4 (C−C) linkages and real lignin in water under open air conditions. The selectivity of carbonyl products is controlled by altering the pH between ~7.0 and ~12.0. The current strategy highlights the non‐involvement of any external co‐catalyst, oxidant, radical additives, and/or destructive organic solvents. The catalyst shows a wide substrate scope and eminent functional group tolerance. The upscaled multigram synthesis using an inexpensive catalyst and easily available oxidant evidences the practical utility of the developed protocol. A plausible mechanism has been proposed with the help of a few controlled experiments, and kinetic and computational studies.

  摘要 醇基和 β-O-4 (C-C) 链广泛存在于生物质原料中，它们是丰富的可再生增值化学品资源。利用露天空气作为氧化剂，以可控方式开发原料材料的直接氧化或氧化裂解的可持续方案，是生产具有重要工业价值的羰基化合物的一项具有启发性的任务。此外，将木质素氧化解聚成精细化学品近来也引起了人们的兴趣。在此，我们报告了首个催化剂系统实例，该催化剂系统可激活大气中的分子氧，在露天条件下对醇类、β-O-4（C-C）连接和水中真正的木质素等原料进行受控氧化和氧化裂解/解聚。羰基产物的选择性可通过在 ~7.0 和 ~12.0 之间改变 pH 值来控制。目前的策略突出了不使用任何外部助催化剂、氧化剂、自由基添加剂和/或破坏性有机溶剂的特点。该催化剂具有广泛的底物范围和出色的官能团耐受性。使用廉价的催化剂和易于获得的氧化剂进行多克级合成，证明了所开发方案的实用性。在一些对照实验、动力学和计算研究的帮助下，我们提出了一种合理的机制。
• Etlis; Razuwaew, Zhurnal Obshchei Khimii, 1957, vol. 27, p. 3092,3094; engl. Ausg. S. 3132, 3134
  作者：Etlis、Razuwaew

  DOI：——

  日期：——
• OKABAYASHI, ICHIZO, J. HETEROCYCL. CHEM., 1982, 19, N 2, 437-438
  作者：OKABAYASHI, ICHIZO

  DOI：——

  日期：——
• COMPOUND AND ORGANIC ELECTRO-OPTICAL DEVICE CONTAINING THE SAME
  申请人：Shanghai Tianma AM-OLED Co., Ltd.

  公开号：US20200395554A1

  公开（公告）日：2020-12-17

  Provided are a compound and an organic electro-optical device containing the same. The compound has a structure represented by Formula I. The organic electro-optical device comprises an anode, a cathode, and at least one organic thin film layer located between the cathode and the anode. The molecule of the compound provided by the present disclosure has higher rigidity, a large conjugated system, a deeper LUMO energy level, a higher triplet energy level and good molecular stability, and is not easy to crystallize, and thus the compound can be used as an electron transport material or a hole blocking material of the organic electro-optical device, facilitating the reduction of the turn-on voltage of the device, the improvement of current efficiency and the increase of service life.