6,13-dipropyl-5,14-dihydropentacene | 1003612-63-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: 6,13-dipropyl-5,14-dihydropentacene
• CAS: 1003612-63-2
• 化学式: C₂₈H₂₈
• 分子量: 364.53
• InChiKey: IOYBKSYQEUUQSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  6,13-dipropyl-5,14-dihydropentacene 、 2,3-二氯-5,6-二氰基-1,4-苯醌 以 甲苯 为溶剂， 反应 3.0h， 以42%的产率得到18,19-dichloro-17,20-dioxo-6,13-dipropyl-5,14-dihydro-5,14-[1,2]benzenopentacene-15,16-dicarbonitrile
  参考文献：
  名称：

  Isolation of 6,13-Dipropylpentacene and Its Tautomerization

  摘要：

  6,13-Dipropyl-5,14-dihydropentacene was aromatized by the combination of the formation of pentacene-DDQ adduct and abstraction of DDQ from the pentacene-DDQ adduct with 50 equiv of gamma-terpinene to gibe 6,13-dipropylpentacene cleanly. It was stable and isolable. In the presence of a catalytic amount of acid, 6,13-dipropylpentacene was isomerized to its tautomer.

  DOI：

  10.1021/ja076819v
• 作为产物：
  描述：

  1,2-bis(2-hexynyl)benzene 、 2,3-二碘萘 在 dibutylbis(cyclopentadienyl)zirconium 、 N,N-二甲基丙烯基脲 、 copper(l) iodide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 15.0h， 以32%的产率得到6,13-dipropyl-5,14-dihydropentacene
  参考文献：
  名称：

  Isolation of 6,13-Dipropylpentacene and Its Tautomerization

  摘要：

  6,13-Dipropyl-5,14-dihydropentacene was aromatized by the combination of the formation of pentacene-DDQ adduct and abstraction of DDQ from the pentacene-DDQ adduct with 50 equiv of gamma-terpinene to gibe 6,13-dipropylpentacene cleanly. It was stable and isolable. In the presence of a catalytic amount of acid, 6,13-dipropylpentacene was isomerized to its tautomer.

  DOI：

  10.1021/ja076819v

文献信息

• Synthesis of acenes via coupling of 1,4-dilithiobutadienes with diiodoarenes in the presence of CuCl
  作者：Lishan Zhou、Kiyohiko Nakajima、Ken-ichiro Kanno、Tamotsu Takahashi

  DOI：10.1016/j.tetlet.2009.02.191

  日期：2009.6

  prepared from diiodobutadienes reacted with diiodobenzene or diiodonaphthalene to afford substituted naphthalene, anthracene, dihydronaphthacene, and dihydropentacene derivatives in the presence of CuCl and DMPU. Dihydronaphthacene and dihydropentacene derivatives were converted into the corresponding naphthacene and pentacene derivatives.

  由二碘丁二烯制得的二硫代丁二烯与二碘苯或二碘萘反应，在CuCl和DMPU存在下，得到取代的萘，蒽，二氢萘和二氢并五苯衍生物。将二氢并四苯并二氢并五苯衍生物转化为相应的并四苯并五并苯衍生物。
• Synthetic Access to Pentacene‐Silylene Adducts via Dehydrogenative Silylation of a 5,14‐Dihydropentacene with a Stable Silylene
  作者：Taichi Koike、Takeaki Iwamoto

  DOI：10.1002/ejoc.202100296

  日期：2021.4.22

  Pentacene‐silylene adducts were easily accessed by the reaction of 6,13‐dipropyl‐5,14‐dihydropentacene with a thermally stable divalent silicon species (silylene). The reaction is proposed to proceed through sequential 1,4‐dehydrogenation and (1+4) cycloaddition of the silylene which demonstrates the potential utility of a silylene in acene synthesis.

  通过1,13-二丙基-5,14-二氢并五苯与热稳定的二价硅物种（亚甲硅烷基）的反应可轻松获得并五苯-亚甲硅烷基加合物。建议该反应通过依次进行甲硅烷基的1,4-脱氢和（1 + 4）环加成反应进行，这证明了甲硅烷基在并苯合成中的潜在效用。
• Isolation of 6,13-Dipropylpentacene and Its Tautomerization
  作者：Tamotsu Takahashi、Ken Kashima、Shi Li、Kiyohiko Nakajima、Ken-ichiro Kanno

  DOI：10.1021/ja076819v

  日期：2007.12.1

  6,13-Dipropyl-5,14-dihydropentacene was aromatized by the combination of the formation of pentacene-DDQ adduct and abstraction of DDQ from the pentacene-DDQ adduct with 50 equiv of gamma-terpinene to gibe 6,13-dipropylpentacene cleanly. It was stable and isolable. In the presence of a catalytic amount of acid, 6,13-dipropylpentacene was isomerized to its tautomer.