4-thia-1,7-methano[11]annulene-2,6-dione | 159640-23-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-thia-1,7-methano[11]annulene-2,6-dione
• 英文别名: 4-Thiabicyclo[5.4.1]dodeca-1(11),7,9-triene-2,6-dione
• CAS: 159640-23-0
• 化学式: C₁₁H₁₀O₂S
• 分子量: 206.265
• InChiKey: PQHPVOUTBQBROJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-thia-1,7-methano[11]annulene-2,6-dione 在 sodium methylate 、 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 (10Z)-20,20-dioxo-2-oxa-20λ6-thiapentacyclo[9.8.1.14,9.113,18.01,3]docosa-4,6,8,10,13,15,17-heptaene-12,19-dione
  参考文献：
  名称：

  Synthesis and properties of anti, anti-8,17-Epithia-1,6;10,15-bismethano[18]annulene-7,18-dione and its dicationic species

  摘要：

  The titled quinone compound has been synthesized and the X-ray crystallographic analysis of this compound revealed that it has anti-anti-configuration for stereochemical relationship between two methylene and sulfur bridges. Its H-1 C-13 NMR spectra in D2SO4 indicate that the cationic species formed by protonation has localized positive charges on the carbony carbons, mainly due to the unfavorable p-orbital overlap. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10203-9
• 作为产物：
  描述：

  1,6-diacetylcyclohepta-1,3,5-triene 在 sodium sulfide 、 copper(ll) bromide 作用下， 以 氯仿 、 水 、 丙酮 为溶剂， 反应 17.0h， 生成 4-thia-1,7-methano[11]annulene-2,6-dione
  参考文献：
  名称：

  抗-6,15-上皮-8,13-甲氧基-苯并[ d ] [14]环戊烯-7,14-二酮及其阳离子和双阴离子类化合物的合成及性能

  摘要：

  已合成标题化合物，其在D 2 SO 4中的1 H和13 C NMR光谱表明，由于亚甲基和硫之间的反构型，由于不利的共轭作用，质子化形成的阳离子物种在羰基碳上具有局部正电荷桥梁。

  DOI：

  10.1016/0040-4039(94)85326-6

文献信息

• Synthesis and conformation of 3,10-di(t-butyl)- and 3,10-dichloro-4,9-methanothia[11]annulenes
  作者：Ryuta Miyatake、Shigeyasu Kuroda、Takanori Kajioka、Akihide Taketani、Mitsunori Oda

  DOI：10.1016/s0040-4020(02)00353-8

  日期：2002.5

  First two derivatives of 4,9-methanothia[11]annulene, 3,10-di(t-butyl)- and 3,10-dichloro-4,9-methanothia[11]annulenes (4 and 5), were synthesized from the diketosulfide 6. Spectroscopic properties and X-ray crystallographic analyses revealed that 4 exists as an anti-conformer in respect of stereochemical relationship between the methano bridge and the sulfur atom both in solid state and in solution

  由以下化合物合成了4,9-甲硫基[11]环戊烯的前两个衍生物3,10-二（叔丁基）-和3,10-二氯-4,9-甲硫基[11]环戊烯（4和5）。二酮硫醚6。光谱性质和X射线晶体学分析表明，就固态和溶液中的甲醇桥和硫原子之间的立体化学关系而言，4作为反式构象异构体而存在，而5与对苯二酚的相似性作为顺式构象异构体存在。4，9-甲硫噻[11]环戊烯的母体（3）。
• Zuo, Shengli; Kuroda, Shigeyasu; Oda, Mitsunori, Heterocycles, 2001, vol. 54, # 1, p. 159 - 170
  作者：Zuo, Shengli、Kuroda, Shigeyasu、Oda, Mitsunori、Kuramoto, Shin-Ya、Mizukami, Yoshihiro、Fukuta, Atsushi、Hirano, Yukiyasu、Nishikawa, Teruhiko、Furuta, Shinji、Miyatake, Ryuta、Shaheen、Kajioka, Takanori、Kyogoku, Mayumi

  DOI：——

  日期：——
• Duplicated ring enlargement of 4,9-methanothia[11]annulene to 6,11-methanothia[15]annulene
  作者：Shigeyasu Kuroda、Rie Kasai、Ryo Nagaya、Ryuta Miyatake、Yoshikazu Horino、Naoko Matsumoto、Mitsunori Oda

  DOI：10.1016/j.tetlet.2010.11.072

  日期：2011.3

  3,10-Dipyrrolidinyl-4,9-methanothia[11]annulene reacts with excess dimethyl acetylenedicarboxylate (DMAD) in refluxing toluene to give ring-enlarged 6,11-methanothia[15]annulene. X-ray crystallographic analysis of the product shows two different cis,trans-dienyl parts in the ring system. Product formation possibly involves pi-facial selective addition of the enamine with DMAD and torque-selective ring opening of the intermediate cyclobutenes. (c) 2010 Elsevier Ltd. All rights reserved.