4-(4-(diethylamino)-2-methylphenyl)naphthalene-1,2-dione | 1130291-75-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(4-(diethylamino)-2-methylphenyl)naphthalene-1,2-dione
• 英文别名: 4-[4-(diethylamino)-2-methyl-phenyl]-[1,2]naphthoquinone；4-[4-(Diethylamino)-2-methylphenyl]naphthalene-1,2-dione；4-[4-(diethylamino)-2-methylphenyl]naphthalene-1,2-dione
• CAS: 1130291-75-6
• 化学式: C₂₁H₂₁NO₂
• 分子量: 319.403
• InChiKey: AWRLLSWENZSMGK-UHFFFAOYSA-N

物化性质

• 熔点：
  143-147 °C
• 沸点：
  485.1±45.0 °C(predicted)
• 密度：
  1.174±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-(diethylamino)-2-methylphenyl)naphthalene-1,2-dione 在 盐酸羟胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.33h， 生成 N,N-diethyl-3-methyl-4-(1,3,3-trimethylspiro[indoline-2,2'-naphtho[1,2-b][1,4]oxazin]-6'-yl)aniline
  参考文献：
  名称：

  A Two-Stage Continuous-Flow Synthesis of Spirooxazine Photochromic Dyes

  摘要：

  报告采用连续流工艺合成了几种已知的和以前未报道过的螺恶嗪光致变色染料。该工艺通过铜催化取代苯胺与萘-1,2-二酮的初始加成反应进行。然后在盐酸羟胺存在下与 1,3,3-三甲基-2-亚甲基吲哚啉反应，得到所需的螺恶嗪产品。然后将这些光致变色染料浇铸到镜片中，对其性能进行初步评估。

  DOI：

  10.1071/ch12435
• 作为产物：
  描述：

  1,2-萘醌 、 N,N-二乙基间甲苯胺 在 copper dichloride 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 0.17h， 以82%的产率得到4-(4-(diethylamino)-2-methylphenyl)naphthalene-1,2-dione
  参考文献：
  名称：

  A Two-Stage Continuous-Flow Synthesis of Spirooxazine Photochromic Dyes

  摘要：

  报告采用连续流工艺合成了几种已知的和以前未报道过的螺恶嗪光致变色染料。该工艺通过铜催化取代苯胺与萘-1,2-二酮的初始加成反应进行。然后在盐酸羟胺存在下与 1,3,3-三甲基-2-亚甲基吲哚啉反应，得到所需的螺恶嗪产品。然后将这些光致变色染料浇铸到镜片中，对其性能进行初步评估。

  DOI：

  10.1071/ch12435

文献信息

• Drastic solid-state fluorescence enhancement behaviour of imidazo[4,5-a]naphthalene-type fluorescent hosts upon inclusion of polyethers and tert-butyl alcohol
  作者：Yousuke Ooyama、Shinobu Nagano、Katsuhira Yoshida

  DOI：10.1016/j.tet.2008.12.003

  日期：2009.2

  As one of the most promising materials for the Construction of desirable solid-state fluorescent system, new solid-state fluorescent host-guest system, which consists of the imidazo[4,5-a]naphthalene-type fluorescent hosts 2 and sterically hindered guest molecules were designed and prepared. The crystals of 2 exhibit sensitive colour change and drastic fluorescence enhancement behaviour upon polyethers (diethylene glycol dimethyl ether (DGDM), diethylene glycol diethyl ether (DGDE) and diethylene glycol dibutyl ether (DGDB)) or tert-butyl alcohol. A comparison of the X-ray crystal structures of the guest-free and polyether- and tert-butyl alcohol-inclusion compounds indicates that the enclathrated polyether or tert-butyl alcohol molecule decrease the pi-stacking between hosts and enlarge the distance between the host-host aromatic planes. On the bases of the spectral data and the crystal Structures, the effects of the enclathrated sterically hindered guest on the drastic solid-state fluorescence enhancement behaviour of the host-guest crystals are discussed. (C) 2008 Elsevier Ltd. All rights reserved
• A Two-Stage Continuous-Flow Synthesis of Spirooxazine Photochromic Dyes
  作者：Mark York、Adriana Edenharter

  DOI：10.1071/ch12435

  日期：——

  A continuous-flow process for the synthesis of several known and previously unreported spirooxazine photochromic dyes is reported. The process proceeds via an initial copper catalysed addition of substituted anilines to naphthalene-1,2-dione. This is followed by reaction with 1,3,3-trimethyl-2-methyleneindoline in the presence of hydroxylamine hydrochloride to give the desired spirooxazine products. The photochromic dyes were then cast into lenses to allow a preliminary evaluation of their properties.

  报告采用连续流工艺合成了几种已知的和以前未报道过的螺恶嗪光致变色染料。该工艺通过铜催化取代苯胺与萘-1,2-二酮的初始加成反应进行。然后在盐酸羟胺存在下与 1,3,3-三甲基-2-亚甲基吲哚啉反应，得到所需的螺恶嗪产品。然后将这些光致变色染料浇铸到镜片中，对其性能进行初步评估。