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 properties of anti-6,15-epithia-8,13-methano-benzo[d][14]annulene-7,14-dione and its dicationic and dianionic species
  作者：Sigeyasu Kuroda、Mitsunori Oda、Shin-ya Kuramoto、Yoshihiro Mizukami、Ichiro Shimao

  DOI：10.1016/0040-4039(94)85326-6

  日期：1994.10

  The titled compound has been synthesized, and its 1H and 13C NMR spectra in D2SO4 indicate that the cationic species formed by protonation has localized positive charges at carbonyl carbons due to the unfavorable conjugation because of the anti configuration between methylene and sulfur bridges.

  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。
• 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）。
• 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.
• Synthesis and properties of anti, anti-8,17-Epithia-1,6;10,15-bismethano[18]annulene-7,18-dione and its dicationic species
  作者：Shigeyasu Kuroda、Mitsunori Oda、Shin-ya Kuramoto、Atsushi Fukuta、Yoshihiro Mizukami、Yoshihiko Nozawa、Ryuta Miyatake、Mayumi Izawa、Ichiro Shimao

  DOI：10.1016/s0040-4039(97)10203-9

  日期：1997.12

  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.
• 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：——