1-(trimethylsilyl)thianthrene 10-oxide | 135489-44-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1-(trimethylsilyl)thianthrene 10-oxide
• 英文别名: 4-trimethylsilylthianthrene 5-oxide；trimethyl-(10-oxothianthren-1-yl)silane
• CAS: 135489-44-0
• 化学式: C₁₅H₁₆OS₂Si
• 分子量: 304.509
• InChiKey: USGXOECMWLEJMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  trimethyl(thianthren-1-yl)silane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以50%的产率得到1-(trimethylsilyl)thianthrene 5-oxide
  参考文献：
  名称：

  Photo SN-bond cleavage and related reactions of thianthrene sulfilimine derivatives

  摘要：

  Several 1- and 2-substituted thianthrene sulfilimine derivatives were prepared and the selectivity toward oxidation and N-tosylimination under several conditions was studied. In the photolysis of trans-5-(N-p-tosyl) iminothianthrene 10-oxide (trans-10), photo isomerization to cis-10 was observed. Further, photoimino-transferreaction of sulfilimines and their 10-mono- and -dioxide derivatives to sulfides was intensively studied to make clear the ability as nitrene precursors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.004

文献信息

• Synthesis of 4,6-disubstituted thianthrenes; X-ray crystal structures of 4,6-diphenylthianthrene and 1-tetrathiafulvalenylnaphthalene
  作者：James M. Lovell、Roy L. Beddoes、John A. Joule

  DOI：10.1016/0040-4020(96)00145-7

  日期：1996.3

  Lithiation of thianthrene 5-oxide, then trapping with chlorotrimethylsilane gave 4-mono-, 4,6-di, 4b, and 4,6,9-tri-TMS derivatives. Reduction of oxide 4b to the thianthrene followed by reaction with bromine gave 4,6-dibromothianthrene which coupled smoothly with phenylboronic acid producing 4,6-diphenylthianthrene, 5c. The crystal structures of 5c and of 4-(1-naphthalenyl)-2-(1,3-dithiol-2-ylidene)-1

  氧化噻吩5-氧化物，然后用三甲基氯硅烷捕集，得到4-单-，4,6-di，4b和4,6,9-tri-TMS衍生物。将氧化物4b还原成噻吨，然后与溴反应，得到4，6-二溴噻吨，其与苯基硼酸平滑地偶联，产生4，6-二苯基噻吨5c。测定了5c和4-（1-萘基）-2-（1，3-二硫醇-2-亚烷基）-1，3-二硫醇的晶体结构。
• A Convenient Preparation of Sterically Crowded 1,9-Disubstituted Dibenzothiophenes and 3,3'-Disubstituted Diaryl Sulfides
  作者：Naomichi Furukawa、Takeshi Kimura、Yoji Horie、Satoshi Ogawa

  DOI：10.3987/com-91-5683

  日期：——

  Thianthrene-5-oxide (1) reacted with 2.2 equivalents of lithium diisopropylamide to give 4,6-dilithiated 1 which was converted to 4,6-disubstituted thianthrene-5-oxides (3). 3 afforded sterically crowded 1,9-disubstituted dibenzothiophenes (4) in moderate yields on treatment with n-butyllithium or phenyllithium.