dimethyl 5,9b-dihydro-5,9b-benzonaphtho[1,2-b]thiohene-2,3-dicarboxylate | 1312710-08-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: dimethyl 5,9b-dihydro-5,9b-benzonaphtho[1,2-b]thiohene-2,3-dicarboxylate
• CAS: 1312710-08-9
• 化学式: C₂₂H₁₆O₄S
• 分子量: 376.433
• InChiKey: UBTNHIRQNPUWGD-CAJLXGCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  dimethyl 5,9b-dihydro-5,9b-benzonaphtho[1,2-b]thiohene-2,3-dicarboxylate 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 15.0h， 以90%的产率得到5,9b-dihydro-5,9b-benzonaphtho[1,2-b]thiohene-2,3-dicarboxylic acid
  参考文献：
  名称：

  Fluorescent 3-Methylene-2,3-Dihydrochalcogenophenes Incorporated in a Rigid Dibenzobarrelene Skeleton

  摘要：

  The fluorescent 3-methylene-2,3-dihydroselenophene derivative (Phi(F) = 0.86 in CH2Cl2) incorporated in a dibenzobarrelene skeleton was synthesized by the reaction of a four-membered selenaplatinacycle with dimethyl acetylenedicarboxylate (DMAD) or reaction of bis(dibenzobarrelenyl) diselenide with DMAD in the presence of Pd(PPh3)(4) and PPh3. A fluorescent sulfur homologue (Phi(F) = 1.0 in CH2Cl2) was also synthesized by the reaction of bis(dibenzobarrelenyl) disulfide with DMAD in the presence of Pd(PPh3)(4). Selected chemical transformations of these diesters were also investigated.

  DOI：

  10.1021/ol2013523
• 作为产物：
  描述：

  9-溴-9,10-二氢-9,10-乙烯蒽 在 四(三苯基膦)钯 、 叔丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 、 正戊烷 为溶剂， 反应 64.0h， 生成 dimethyl 5,9b-dihydro-5,9b-benzonaphtho[1,2-b]thiohene-2,3-dicarboxylate
  参考文献：
  名称：

  Fluorescent 3-Methylene-2,3-Dihydrochalcogenophenes Incorporated in a Rigid Dibenzobarrelene Skeleton

  摘要：

  The fluorescent 3-methylene-2,3-dihydroselenophene derivative (Phi(F) = 0.86 in CH2Cl2) incorporated in a dibenzobarrelene skeleton was synthesized by the reaction of a four-membered selenaplatinacycle with dimethyl acetylenedicarboxylate (DMAD) or reaction of bis(dibenzobarrelenyl) diselenide with DMAD in the presence of Pd(PPh3)(4) and PPh3. A fluorescent sulfur homologue (Phi(F) = 1.0 in CH2Cl2) was also synthesized by the reaction of bis(dibenzobarrelenyl) disulfide with DMAD in the presence of Pd(PPh3)(4). Selected chemical transformations of these diesters were also investigated.

  DOI：

  10.1021/ol2013523

文献信息

• Reactions of Bis(dibenzobarrelenyl) Dichalcogenides with a Palladium(0) Complex: Unexpected Formations of Mononuclear Chalcogenide(dichalcogenolato)palladium(II) Complexes and Dichalco­genahexacyclo Compounds
  作者：Norio Nakata、Yuki Yamaguchi、Akihiko Ishii

  DOI：10.1002/ejic.201402518

  日期：2014.10

  Thermal reactions of bis(dibenzobarrelenyl) dichalcogenides [(DbbS)2 and (DbbSe)2] with [Pd(PPh3)4] in toluene afforded novel mononuclear chalcogenide(dichalcogenolato)PdII complexes [Pd(EDbb-12-EDbb)(EDbb)(PPh3)] (E = S, Se) together with dichalcogenahexacyclo compounds. The reaction in the presence of PPh3 in toluene at 110 °C led to a cyclometalation to furnish the corresponding four-membered 1

  双（二苯并芘基）二硫属元素化物 [(DbbS)2 和 (DbbSe)2] 与 [Pd(PPh3)4] 在甲苯中的热反应提供了新型单核硫属元素（二硫属原）PdII 配合物 [Pd(EDbb-12-EDbb)(EDbb) (PPh3)] (E = S, Se) 以及二硫属六环化合物。在 PPh3 存在下在甲苯中于 110°C 下进行的反应导致环金属化，以提供相应的四元 1,2-硫族元素钯环 [Pd(EDbb)(PPh3)2] (E = S, Se) 和二硫属六环化合物。这些 PdII 配合物和环化产物的结构在它们的 NMR 光谱数据和 X 射线分析的基础上得到了充分表征。在 [Pd(SDbb-12-SDbb)(SDbb)(PPh3)] 的结晶状态下，两个硫醇合硫原子相对于 PPh3 占据顺式位置，
• Fluorescent 3-Methylene-2,3-Dihydrochalcogenophenes Incorporated in a Rigid Dibenzobarrelene Skeleton
  作者：Akihiko Ishii、Yuki Yamaguchi、Norio Nakata

  DOI：10.1021/ol2013523

  日期：2011.7.15

  The fluorescent 3-methylene-2,3-dihydroselenophene derivative (Phi(F) = 0.86 in CH2Cl2) incorporated in a dibenzobarrelene skeleton was synthesized by the reaction of a four-membered selenaplatinacycle with dimethyl acetylenedicarboxylate (DMAD) or reaction of bis(dibenzobarrelenyl) diselenide with DMAD in the presence of Pd(PPh3)(4) and PPh3. A fluorescent sulfur homologue (Phi(F) = 1.0 in CH2Cl2) was also synthesized by the reaction of bis(dibenzobarrelenyl) disulfide with DMAD in the presence of Pd(PPh3)(4). Selected chemical transformations of these diesters were also investigated.