bis-{(4,5-methylnendioxy)benzylidene}-1,4-phenylenediamine | 4189-11-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: bis-{(4,5-methylnendioxy)benzylidene}-1,4-phenylenediamine
• 英文别名: N,N'-Bis(piperonylidene)-1,4-phenylenediamine；1-(1,3-benzodioxol-5-yl)-N-[4-(1,3-benzodioxol-5-ylmethylideneamino)phenyl]methanimine
• CAS: 4189-11-1
• 化学式: C₂₂H₁₆N₂O₄
• 分子量: 372.38
• InChiKey: NLOKQYWTLFMAJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  bis-{(4,5-methylnendioxy)benzylidene}-1,4-phenylenediamine 、 1-溴环己烷羧酸甲酯 在 mercury dichloride 、 锌 作用下， 以 六甲基磷酰三胺 、 甲苯 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  1-溴环己烷甲酸甲酯与N，N'-（1,4-亚苯基）双（1-芳基甲亚胺）的Reformatsky反应

  摘要：

  摘要由1-溴环己烷甲酸甲酯与N，N '-（1,4-亚苯基）双（1-芳基甲亚胺）反应制得的Reformatsky试剂可生成2,2'-（1,4-亚苯基）双[3-芳基-2- azaspiro [3.5] nonan-1-ones的结果，是连续向底物的C = N双键进行亲核加成以及相应中间体的分子内环化作用。通过在与等摩尔量的席夫碱和Reformatsky试剂的反应中分离2- [4-（芳基亚甲基氨基）苯基] -3-芳基-2-氮杂螺[3.5]壬基-1-酮来证明逐步反应机理。

  DOI：

  10.1134/s107042802006010x
• 作为产物：
  描述：

  胡椒醛 、 对苯二胺 以 甲苯 为溶剂， 生成 bis-{(4,5-methylnendioxy)benzylidene}-1,4-phenylenediamine
  参考文献：
  名称：

  Synthesis of new DOPO derivatives and investigation of their synergistic effect with APP–PEI on the flame retardancy of epoxy composite

  摘要：

  Sixteen DOPO derivatives FR1–FR16 were successfully synthesized. The DOPO derivatives and APP-PEI showed a synergistic effect on the flame retardancy of epoxy. The epoxy composites displayed high fire resistance and good mechanical property.

  DOI：

  10.1039/d4ra00051j

文献信息

• Cyclometallated complexes of bis(N-benzylidene)-1,4-phenylenediamines. Synthesis and crystal structure of [1,4-{](Br)}2C6H4]2: a novel tetranuclear cyclometallated palladium(II) complex
  作者：Jose M. Vila、Miguel Gayoso、Ma Teresa Pereira、Ma Camino Rodriguez、Juan M. Ortigueira、Mark Thornton-Pett

  DOI：10.1016/0022-328x(92)83049-n

  日期：1992.3

  Treatment of 1,4-2,3,4-(Meo)3C6H2C(H) = N-}2C6H4 (a) or 1,4-4,5-(OCH2O)C6H3C(H) = N-}2-C6H4 (b) with palladium(II) acetate gave the cyclometallated acetato-bridged complexes [1,4-Pd[2,3,4-(MeO)3C6HC(H) = N](O2CMe)}2C6H4]n (1a) and [1,4-Pd[4,5-(OCH2O)C6H2C(H) = N](O2CMe)}2-C6H4]n (1b). These were converted into the analogous halide-bridged complexes by treatment with NaX (2a, 2b X = Cl; 3a, 3b X = Br). Reaction of a or b with PdCl2 also affords the chloro-bridged complexes 2a and 2b, which reacted with LiBr to give the bromo-bridged complexes 3a and 3b. The structure of 3a is described. This is the first example of a structurally characterized tetranuclear cyclometallated bromo-bridged palladium(II) complex. Crystals are triclinic, space group P1BAR, with a 1109.1(4), b 1181.5(4). c 1481.5(5) pm, alpha-77.33(3), beta-80.04(3), gamma-82.50(3)-degrees, U 1.857(1) nm3, Z = 1, R = 0.0558 and R(W) = 0.0610, for 3871 independent reflections with I > 2.0-sigma(I). The structure is a centrosymmetric tetranuclear palladium(II) dimer with symmetrically bridging bromine atoms and non-bonding Pd...Pd distance of 366.2(5) pm.
• 10.1007/s11094-024-03119-9
  作者：Deshpande, Shreenivas R.、Mandalamari, Manappa T.、Malagi, Prasad V.、V. M, Chandrashekhar

  DOI：10.1007/s11094-024-03119-9

  日期：——
• Reformatsky Reaction of Methyl 1-Bromocyclohexanecarboxylate with N,N′-(1,4-Phenylene)bis(1-arylmethanimines)
  作者：E. A. Nikiforova、D. V. Baibarodskikh、N. F. Kirillov、L. A. Glavatskikh

  DOI：10.1134/s107042802006010x

  日期：2020.6

  AbstractReformatsky reagent prepared from methyl 1-bromocyclohexanecarboxylate reacted with N,N′-(1,4-phenylene)bis(1-arylmethanimines) to produce 2,2′-(1,4-phenylene)bis[3-aryl-2-azaspiro[3.5]nonan-1-ones] as a result of successive nucleophilic additions to the C=N double bonds of the substrate and intramolecular cyclization of the corresponding intermediates. The stepwise reaction mechanism was proved by the isolation

  摘要由1-溴环己烷甲酸甲酯与N，N '-（1,4-亚苯基）双（1-芳基甲亚胺）反应制得的Reformatsky试剂可生成2,2'-（1,4-亚苯基）双[3-芳基-2- azaspiro [3.5] nonan-1-ones的结果，是连续向底物的C = N双键进行亲核加成以及相应中间体的分子内环化作用。通过在与等摩尔量的席夫碱和Reformatsky试剂的反应中分离2- [4-（芳基亚甲基氨基）苯基] -3-芳基-2-氮杂螺[3.5]壬基-1-酮来证明逐步反应机理。
• Synthesis of new DOPO derivatives and investigation of their synergistic effect with APP–PEI on the flame retardancy of epoxy composite
  作者：Cong Trinh Duc、Linh Chi Nguyen、Phuc Ban Van、Ha Thanh Nguyen、Tuyet Anh Dang Thi、Giang Le-Nhat-Thuy、Quynh Giang Nguyen Thi、Phuong Hoang Thi、Tuan Anh Nguyen、Quang Vinh Tran、Hung Tran Quang、Mai Ha Hoang、Tuyen Nguyen Van

  DOI：10.1039/d4ra00051j

  日期：2024.2.7

  Sixteen DOPO derivatives FR1–FR16 were successfully synthesized. The DOPO derivatives and APP-PEI showed a synergistic effect on the flame retardancy of epoxy. The epoxy composites displayed high fire resistance and good mechanical property.