1,3-dimethyl-1H-perimidin-2(3H)-one | 2306-08-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类 - 二氮杂萘
• 英文名称: 1,3-dimethyl-1H-perimidin-2(3H)-one
• 英文别名: 1,3-dimethylperimidone；1,3-Dimethylperimidon；1,3-dimethylperimidin-2-one
• CAS: 2306-08-3
• 化学式: C₁₃H₁₂N₂O
• mdl: MFCD00476495
• 分子量: 212.251
• InChiKey: WZWDLGNDEHWENW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-1H-perimidin-2(3H)-one 在 氢氧化钾 作用下， 反应 3.0h， 以97%的产率得到1,8-二(甲基氨基)萘
  参考文献：
  名称：

  Konstantinchenko, A. A.; Pozharskii, A. A,; Stepanova, V. N., Russian Journal of Organic Chemistry, 1993, vol. 29, # 7.2, p. 1195 - 1199

  摘要：

  DOI：
• 作为产物：
  描述：

  1,8-二(甲基氨基)萘 、 氰乙酸乙酯 反应 0.33h， 以81%的产率得到1,3-dimethyl-1H-perimidin-2(3H)-one
  参考文献：
  名称：

  pleiadiene 60的杂环类似物。1-甲基-2-氯甲基亚丙基的合成及性质

  摘要：

  DOI：

  10.1007/bf00475607

文献信息

• テトラアミン誘導体及びその合成方法並びにそれを用いた有機エレクトロニクスデバイス
  申请人：国立大学法人山形大学

  公开号：JP2015151372A

  公开（公告）日：2015-08-24

  【課題】有機薄膜トランジスタ（有機ＴＦＴ）や有機エレクトロルミネッセンス素子（有機ＥＬ素子）、有機薄膜太陽電池等の塗布型有機半導体材料として用いることができる、ナフタレン又はペリレンを骨格とする環状尿素結合を持つテトラアミン誘導体及びその合成方法の提供。【解決手段】塗布型有機半導体材料として、例えば下記反応式により得られるナフタレンを骨格とする環状尿素結合を持つテトラアミン誘導体を用いる。【選択図】なし

  提供一种具有以萘或苝为骨架的环状尿素结合的四胺衍生物及其合成方法，可用作有机薄膜晶体管（有机TFT）或有机电致发光元件（有机EL元件）、有机薄膜太阳能电池等涂覆型有机半导体材料。作为涂覆型有机半导体材料，可以使用具有以萘为骨架的环状尿素结合的四胺衍生物，例如通过以下反应式获得。【选择图】无
• ——
  作者：V. I. Sorokin、V. A. Ozeryanskii、A. F. Pozharskii

  DOI：10.1023/a:1019615206870

  日期：——

  New methods were proposed for synthesizing 1,4,5,8-tetrakis(dimethylamino)naphthalene with an overall yield of 4 to 12% to replace the known procedure ensuring an overall yield of 2%. Catalytic hydrogenation was shown to be inapplicable for preparation of polyaminonaphthalenes from nitro compounds having 3 or 4 nitro gruops in the alpha-positions. Nucleophilic amination of 1,5-dinitronaphthalene in the system NH2OH/NaOH/MeOH yields 1-amino-4-nitronaphthalene. The nitration of 1,5-bis(p-tolylsulfonylamino)naphthalene leads to formation of 2,6-dinitro rather than 4,8-dinitro derivative, as it was believed formerly. This was confirmed by transformation of the latter into 1,2,5,6-tetrakis(dimethylamino)naphthalene. 3-Nitro, 2,6-dinitro, 2,6-diamino, and 2,4,6,8-tetranitro derivatives of 1,5-bis(dimethylamino)naphthalene, nitro and amino derivatives of 1,4,5-tris(dimethylamino)naphthalene, and 4,5-diamino-1,8-bis(methylamino)naphthalene were synthesized. By treatment with perchloric acid 1,4,5,8-tetrakis(dimethylamino)naphthalene was oxidized to 2,3-dihydroperimidinium salt.
• Kurasov, L. A.; Posharskii, A. F.; Kuz'menko, V. V., Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, p. 1735 - 1738
  作者：Kurasov, L. A.、Posharskii, A. F.、Kuz'menko, V. V.

  DOI：——

  日期：——
• Heterocyclic Analogs of Pleiadiene: LXXIV. peri-Cyclizations in the Perimidine Series. Synthesis of 1,3-Diazapyrene Derivatives
  作者：I. V. Borovlev、O. P. Demidov、A. V. Aksenov、A. F. Pozharskii

  DOI：10.1023/b:rujo.0000044557.95160.e5

  日期：2004.6

  Reactions of perimidines and perimidin-2-ones with alpha,beta-unsaturated carbonyl compounds gave various 1,3-diazapyrene derivatives. Acylation of 1-methylperimidine, perimidin-2-one, and 1-methylperimidin-2-one with cinnamoyl chloride in the presence of AlBr3 is accompanied by peri-fusion at the 6,7-position and dearylation of the intermediate product. Under analogous conditions, 1,3-dimethyl-2,3-dihydroperimidine gave rise to 6-cinnamoyl-1,3-dimethyl-2,3-dihydroperimidine. Reactions of perimidin-2-ones with 1,3-diphenyl-2-propenone in polyphosphoric acid resulted in peri-fusion at the 6,7-position, and with acetylacetone, at the 1,9-position.
• N,N'-Bridged 1,4,5,8-Tetrakis(methylamino)naphthalenes and Their Radical Cations. Comparison with 1,4,5,8-Tetrakis(dimethylamino)naphthalene and Related Radical Cations
  作者：Thomas Barth、Franz A. Neugebauer

  DOI：10.1021/jo00122a015

  日期：1995.9

  Syntheses of 3,8-dihydro-1,3,6,8-tetramethylpyrimido[4,5,6-gh]perimidine-2,7-(1H,6H)-dione (2), 1,2,3,6,7,8-hexahydro-1,3,6,8-tetramethylpyrimido[4,5,6-gh]perimidine (3), and 3,6,7,8-tetrahydro-1,3,6,8-tetramethylpyrimido[4,5,6-gh]perimidin-2(1H)-one (4) are reported. The corresponding radical cations were generated by oxidation with iodine or tris(4-bromophenyl)amminium hexachloroantimonate and were studied by ESR and ENDOR for comparison with the 1,4,5,8-tetrakis(dimethylamino)naphthalene radical cation (1(.+)), The ESR results of 2(.+)-4(.+), however, ave no indications which could explain the widely different exo (3.54 G) and endo (1.77 G) N-methyl proton splittings in 1(.+).