二氯化乙二亚胺酰基,二[4-(1,1-二甲基乙基)苯基]- | 189114-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 二氯化乙二亚胺酰基,二[4-(1,1-二甲基乙基)苯基]-
• 英文名称: bis(p-tert-butylphenylimidoyl)chloride
• 英文别名: oxalic acid N,N'-bis(4-tert-butylphenyl)imidoyl dichloride；N,Na(2)-Bis[4-(1,1-dimethylethyl)phenyl]ethanediimidoyl dichloride；N,N'-bis(4-tert-butylphenyl)ethanediimidoyl dichloride
• CAS: 189114-72-5
• 化学式: C₂₂H₂₆Cl₂N₂
• 分子量: 389.368
• InChiKey: UROTWOMBXSJTOY-UHFFFAOYSA-N

物化性质

• 沸点：
  477.6±48.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二氯化乙二亚胺酰基,二[4-(1,1-二甲基乙基)苯基]- 在 氨 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以85%的产率得到1-N',2-N'-bis(4-tert-butylphenyl)ethanediimidamide
  参考文献：
  名称：

  Mueller; Beckert; Goerls, Synthesis, 2001, # 4, p. 601 - 606

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N'-di-t-butylphenyloxamide 在 五氯化磷 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以86%的产率得到二氯化乙二亚胺酰基,二[4-(1,1-二甲基乙基)苯基]-
  参考文献：
  名称：

  Deeply Colored Polymers Containing 1,3,4,6-Tetraarylpyrrolo[3,2-b]pyrrole-2,5-dione (IsoDPP) Units in the Main Chain

  摘要：

  Synthesis and characteristic properties of polymers P1-P4 containing 1,3,4,6-tetraarylated pyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP) units in the main chain are described. PI and P2 were prepared upon palladium-catalyzed polycondensation of 3,6-bis(4-bromophenyl)-1,4-bis(4-tert-butylphenyl)pyrrolo[3,2-b]pyrrole-2,S-dione (M1) or 1,4-bis(4-bromophenyl)-3,6-bis(4-tert-butylphenyl)pyrrolo[3,2-b]-pyrrole-2,5-dione (M2) and 2,2'-(9,9-dihexyl-9H-fluoren-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (M4), while P3 and P4 were synthesized upon polycondensation of 3,6-bis(5-bromothien-2-yl)-1,4-bis(4-dodecylphenyl)pyrrolo[3,2-b]pyrrole-2,5-dione (M3) and 2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene (MS) or 9-(2-ethylhexyl)-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole (M6). Deeply colored polymers with molecular weights between 3.5 and 22, kDa were obtained. The polymers were soluble in common organic solvents such as dichloromethane, chloroform, and tetrahydrofuran. All polymers exhibit broad absorption bands with high extinction coefficients (epsilon > 2 x 10(4) L mol(-1) cm(-1)) but weak fluorescence, the quantum yields being below 1%. Although P1 and P2 are isomers, their optical properties are rather different. P1 with polyconjugated backbone exhibits an absorption maximum at 409 nm, while P2 has a maximum at 360 nm due to interruption of pi-conjugation at the lactam N atoms. The presence of thienyl-isoDPP units in the backbone causes a red-shift of the absorption to 489 nm (P3) and 435 nm (P4). All polymers exhibit nearly irreversible oxidation and reduction behavior. Bandgaps of the polymers with phenyl-substituted isoDPP units (PI and P2) are at about 2 eV, while those of polymers with thienyl-substituted isoDPP (P3 and P4) are at about 1.5 eV.

  DOI：

  10.1021/ma300483u

文献信息

• Multi-step Redox Systems with NIR-Fluorescence Based on 4H-Imidazoles
  作者：Martin Matschke、Rainer Beckert

  DOI：10.3390/12040723

  日期：——

  A new class of 4H-imidazoles was synthesized starting from fused-ring aromatic dinitriles. Strong bathochromic shifts of the longest wavelength absorptions were observed in the corresponding UV/vis spectra due to a conversion of the merocyanine chromophores into cyanines/(aza)oxonoles upon protonation/deprotonation of the 4H-imidazoles. Novel boratetraazapentalenes were synthesized via a cyclization

  从稠环芳族二腈开始合成了一类新的4H-咪唑。由于在4H-咪唑质子化/去质子化后，花青生色团转变为花青/（氮杂）恶唑，因此在相应的UV / vis光谱中观察到了最长吸收波长的强烈红移。通过与三氟化硼的环化反应合成了新的硼酸根氮杂戊烯。这些带有花青生色团的介电物种不仅显示近红外荧光，而且还作为准可逆多步氧化还原系统的一部分参与。计算得出的大半醌形成常数K（SEM）（3x10（10）至5x10（11））表明相应的自由基阴离子（SEM）具有很高的热力学稳定性。
• New and Efficient Synthesis of Pyrrolo[3,2-<i>b</i>]pyrrole-2,5-diones by Double-Anion-Capture Reactions of Ester Carbanions with Bis(imidoyl)chlorides of Oxalic Acid
  作者：Peter Langer、Jörg Wuckelt、Manfred Döring

  DOI：10.1021/jo991377u

  日期：2000.2.1

  A variety of pyrrolo[3,2-b]pyrrole-2,5-diones were efficiently prepared by a new domino-reaction of ester carbanions with oxalic acid−bis(imidoyl)chlorides. This reaction proceeded by condensation of 2 equiv of the ester with the bis(imidoyl)chloride and subsequent intramolecular attack of the nitrogen atoms of the bis-enamine intermediate onto the ester groups. The products, which can be regarded

  通过酯碳负离子与草酸-双(亚氨基)氯化物的新型多米诺反应有效地制备了多种吡咯并[3,2-b]吡咯-2,5-二酮。该反应通过2当量酯与双(亚氨基)氯化物的缩合和随后双烯胺中间体的氮原子对酯基团的分子内攻击而进行。该产品可被视为戊烯的双内酰胺，由于其光学特性、稳定性和低溶解度，是有用的合成颜料。吡咯并[3,2-b]吡咯-2,5-二酮的UV-vis性质可以通过连接到杂环核上的取代基来有效控制。研究了新环化反应的范围和局限性。
• A New Route to Ring-Fused Pyrazines: Imidazo[4,5-b]Quinoxalines by a Simple Oxidation-Annulation Sequence
  作者：Rainer Beckert、Ernst-Ulrich Würthwein、Svenja Herzog、Gunther Buehrdel、Susann Klimas、Stefan Grimme、Helmar Görls

  DOI：10.1055/s-0029-1217071

  日期：2009.12

  Novel tricyclic 4H-imidazo[4,5-b]quinoxalines were synthesized by a new ortho-annulation process starting from 4H-imidazoles and cerammonium nitrate (CAN) as oxidation reagent in the presence of potassium carbonate as base. This reaction is interpreted as a multi-step reaction involving oxidative radical formation, a radical aromatic substitution and a subsequent redox process. The analysis is supported

  在碳酸钾为碱的存在下，以4 H-咪唑和硝酸铈铵（CAN）为氧化剂，通过新的邻位环化工艺合成了新型三环4 H-咪唑并[4,5- b ]喹喔啉。该反应被解释为涉及氧化自由基形成，自由基芳族取代和随后的氧化还原过程的多步骤反应。高级DFT计算支持该分析。这种新颖的转化为吡嗪的环稠合衍生物的构建开辟了道路。新的三环产品在溶液中显示出强荧光，此外还显示出可逆的氧化还原活性。 胺-杂环-氧化-自由基反应-闭环
• Synthesis and Structure of Thia and Selena Heterocycles Containing Cycloamidine Substructures
  作者：Rainer Beckert、Jan Fleischhauer、Wolfgang Günther、Stefan Kluge、Stefan Zahn、Jennie Weston、Dorothea Berg、Helmar Görls

  DOI：10.1055/s-2007-983834

  日期：2007.9

  Cyclization of a bis-arylimidoyl chloride with an acylselenourea leads to the construction of a 1,3-selenazolidine with a heteroradialene structure. Another reaction of the bis-arylimidoyl chloride (hydrazinolysis) leads to the formation of Δ2-1,2-diazetines, which we have shown previously to be reactive precursors for ring transformation reactions that yield unusual heterocycles. We now demonstrate that the reaction of these Δ2-1,2-diazetines with various isothio- or isoselenocyanates affords an efficient entry to highly substituted 1,3,4-thia- or -selenadiazines. The structures of these novel derivatives were confirmed by NMR and mass spectroscopy, elemental analysis, and X-ray structural analysis. Detailed multidimensional 77Se NMR experiments as well as density functional theory (DFT) calculations show structural specifics of these compounds.

  双芳基咪唑氯化物与酰基硒脲的环化反应导致了具有异构二烯结构的1,3-硒杂唑烷的构建。双芳基咪唑氯化物的另一反应（肼水解）导致了Δ2-1,2-二氮烯的形成，我们之前已表明其是环转化反应的反应性前体，能够生成不寻常的杂环。我们现在证明这些Δ2-1,2-二氮烯与各种异硫氰酸酯或异硒氰酸酯的反应为高度取代的1,3,4-硫或硒二氮烯的合成提供了高效途径。这些新颖衍生物的结构通过NMR质谱、元素分析和X射线结构分析得到了确认。详尽的多维77Se NMR实验以及密度泛函理论（DFT）计算展示了这些化合物的结构特征。
• From Byproducts to Efficient Fluorophores: A Route to the Synthesis of Fluorubines
  作者：Jan Fleischhauer、Rainer Beckert、Yvonne Jüttke、David Hornig、Wolfgang Günther、Eckhard Birckner、Ulrich-W. Grummt、Helmar Görls

  DOI：10.1002/chem.200901961

  日期：2009.11.23

  was confirmed as a novel fluorubine derivative. In continuing our studies to substituted oligoazaacenes, we developed several synthetic entries to build up novel fluorubine derivatives, in which particularly aminobridged bis(quinoxaline)s are the key products for cationic hexaazapentacenes. We would like to discuss the possible formation pathways of these fluorubine derivatives, which exhibit interesting

  双（亚氨）草酸的氯化物与单烷基肼引线的取代的Δ反应2-1,2-二氮杂环丁烷，是用于环转化反应的通用构建基块。证实了一种由强烈橙色/红色荧光为特征的副反应引起的显着产物，是一种新颖的氟比丁衍生物。在继续我们对取代的低聚氮杂氮杂蒽的研究中，我们开发了几种合成的化合物以建立新的氟比丁衍生物，其中特别是氨基桥联的双（喹喔啉）是阳离子六氮杂戊并烷的关键产品。我们想讨论这些氟丁二烯衍生物的可能的形成途径，这些衍生物表现出有趣的光物理和化学性质。所有新衍生物的结构均通过常用的分析方法（NMR光谱，CV，UV / Vis，质谱，元素分析，