9-dibenzobarrelenethiol | 1312710-15-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-dibenzobarrelenethiol
• 英文别名: DbbSH；Tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13,15-heptaene-1-thiol；tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13,15-heptaene-1-thiol
• CAS: 1312710-15-8
• 化学式: C₁₆H₁₂S
• 分子量: 236.337
• InChiKey: BRKVWJCIXKMXSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-dibenzobarrelenethiol 在 四(三苯基膦)钯 、 水 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 56.0h， 生成 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 叔丁基锂 、 sulfur 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 23.0h， 以74%的产率得到9-dibenzobarrelenethiol
  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

• 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.