2,3-naphthalenedicarboxylicthio anhydride | 111722-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-naphthalenedicarboxylicthio anhydride
• 英文别名: Naphtho[2,3-c]thiophene-1,3-dione；benzo[f][2]benzothiole-1,3-dione
• CAS: 111722-80-6
• 化学式: C₁₂H₆O₂S
• 分子量: 214.244
• InChiKey: AFRAAXZVWMNXGP-UHFFFAOYSA-N

物化性质

• 沸点：
  443.9±28.0 °C(Predicted)
• 密度：
  1.476±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2,3-naphthalenedicarboxylicthio anhydride 在 lithium bromide 、 三甲氧基磷 作用下， 以 六甲基磷酰三胺 、 甲苯 为溶剂， 反应 11.0h， 生成 1,3-Bis-[1,3]dithiol-2-ylidene-1,3-dihydro-naphtho[2,3-c]thiophene
  参考文献：
  名称：

  1,3-Bis(1,3-dithiol-2-ylidene)-1,3-dihydrobenzo[c]heterophenes. New Fused Heteocycle-extended Donors and Their Conducting TCNQ-Complexes

  摘要：

  A series of new fused-heterocycle-extended donors have been synthesized by convenient and short-step reactions. Of these benzo[c]furoquinonoid-extended one has the lowest oxidation potential. TCNQ complexes of these donors exhibit fairly high conductivities even when measured on compressed pellets.

  DOI：

  10.3987/com-97-7780
• 作为产物：
  描述：

  2，3-萘二酐 在 sodium sulfide 作用下， 生成 2,3-naphthalenedicarboxylicthio anhydride
  参考文献：
  名称：

  Cava, M. P.; Lakshmikantham, M. V., Phosphorus, Sulfur and Silicon and the Related Elements, 1989, vol. 43, # 1-2, p. 95 - 110

  摘要：

  DOI：

文献信息

• Photochemistry of Arenedicarboxylic Thioanhydride. Insertion of Alkene into C(=O)–S Bond of 1,2- and 2,3-Naphthalenedicarboxylic Thioanhydride
  作者：Yasuo Kubo、Kensen Okusako、Takeo Araki

  DOI：10.1246/cl.1987.811

  日期：1987.5.5

  2-naphthalenedicarboxylic thioanhydride (5a) or its 2,3-isomer with alkenes in acetonitrile gave naphthothiepindiones by insertion of alkenes into C(=O)–S bond of the thioanhydride. Reactions of 5a with cis- and trans-2-butene were stereospecific, demonstrating that the insertion was caused from the singlet excited state of 5a.

  用乙腈中的烯烃照射 1,2-萘二甲酸酐 (5a) 或其 2,3-异构体，通过将烯烃插入硫酐的 C(=O)-S 键，得到萘硫茚二酮。5a 与顺式和反式 2-丁烯的反应是立体定向的，表明插入是由 5a 的单线激发态引起的。
• Methylenecyclopropane as C1 synthetic units: [1+4] cycloaddition via a nickel catalyst
  作者：Tasuku Inami、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1039/c1cc13540f

  日期：——

  Nickel-catalyzed reactions of methylenecyclopropanes and thioanhydrides afford sulfur-containing heterocyclic compounds via [1+4] cycloaddition. The reactions represent a new use for methylenecyclopropane as a possible one-carbon building block to replace carbon monoxide, isocyanides, and Fischer carbene complexes.

  镍催化的亚甲基环丙烷与硫代酸酐的反应可通过[1 + 4]环加成反应生成含硫的杂环化合物。该反应代表了亚甲基环丙烷的一种新用途，它可以取代一氧化碳，异氰酸酯和费歇尔卡宾络合物，成为可能的一碳结构单元。
• KUBO YASUO; OKUSAKO KENSEN; ARAKI TAKEO, CHEM. LETT.,(1987) N 5, 811-814
  作者：KUBO YASUO、 OKUSAKO KENSEN、 ARAKI TAKEO

  DOI：——

  日期：——
• Cava, M. P.; Lakshmikantham, M. V., Phosphorus, Sulfur and Silicon and the Related Elements, 1989, vol. 43, # 1-2, p. 95 - 110
  作者：Cava, M. P.、Lakshmikantham, M. V.

  DOI：——

  日期：——
• 1,3-Bis(1,3-dithiol-2-ylidene)-1,3-dihydrobenzo[c]heterophenes. New Fused Heteocycle-extended Donors and Their Conducting TCNQ-Complexes
  作者：Kazuko Takahashi、Toshihiro Ise

  DOI：10.3987/com-97-7780

  日期：——

  A series of new fused-heterocycle-extended donors have been synthesized by convenient and short-step reactions. Of these benzo[c]furoquinonoid-extended one has the lowest oxidation potential. TCNQ complexes of these donors exhibit fairly high conductivities even when measured on compressed pellets.