N,N'-(1,3-phenylene)bis(2,2-dimethylpropanamide) | 25116-08-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N'-(1,3-phenylene)bis(2,2-dimethylpropanamide)
• 英文别名: N,N'-(1,3-phenylene)-bis-pivalamide；1,3-bis(pivaloylamino)benzene；N,N'-m-phenylene-bis-pivalamide；N.N'-Dipivaloyl-m-phenylendiamin；N,N'-m-Phenylen-bis-pivalamid；N,N'-(1,3-Phenylen)bispivalamid；N-[3-(2,2-dimethylpropanoylamino)phenyl]-2,2-dimethylpropanamide
• CAS: 25116-08-9
• 化学式: C₁₆H₂₄N₂O₂
• 分子量: 276.379
• InChiKey: XVOUKNDICGZRTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-(1,3-phenylene)bis(2,2-dimethylpropanamide) 在 甲醇 、 copper(l) iodide 、 copper(ll) sulfate pentahydrate 、 trans-bis(triphenylphosphine)palladium dichloride 、 一氯化碘 、 potassium carbonate 、 sodium ascorbate 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 水 为溶剂， 反应 39.25h， 生成 N-[2,4-bis[1-(1,3-dioxo-2-tridecan-7-ylbenzo[de]isoquinolin-5-yl)triazol-4-yl]-5-[(1-hydroxy-2,2-dimethylpropylidene)amino]phenyl]-2,2-dimethylpropanimidic acid
  参考文献：
  名称：

  Polarized Naphthalimide CH Donors Enhance Cl^– Binding within an Aryl-Triazole Receptor

  摘要：

  The dipolar character of 1,8-naphthalimide together with polarization of the C-4-H and C-5-H donors has been utilized in receptor 1 to effectively bind chloride alongside triazole and phenylene units. The Cl- binding strength of 1 shows that the naphthalimide provides greater anion stabilization than an unactivated phenylene, and DFT calculations show that its collinear donor array can be a "urea-like" analog for CH center dot center dot center dot anion interactions.

  DOI：

  10.1021/ol202729z
• 作为产物：
  描述：

  三甲基乙酰氯 、 间苯二胺 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到N,N'-(1,3-phenylene)bis(2,2-dimethylpropanamide)
  参考文献：
  名称：

  具有锯齿形 BN 掺杂外围的 peri-Acenoacene 带

  摘要：

  在这里，我们报告了 BN 掺杂石墨烯纳米带的合成，其中锯齿形边缘的外围碳原子已被硼和氮原子选择性地替换为 BN 和 NBN 基序。这包括高产环闭合关键步骤，通过仅使用 BBr 3的N定向硼化反应，允许meta平面化-低聚亚芳基前体，通过形成 B-N 和 B-C 键，得到三-、四-、五-和六-亚芳基纳米带。X 射线单晶衍射研究证实了 BN 和 NBN 图案的形成以及规则掺杂带的锯齿形边缘拓扑结构。室温下的稳态吸收和发射研究表明，随着低聚亚芳基主链的延长，紫外-可见吸收和发射包络发生系统的红移，纳米带发射具有 TADF 成分。所有衍生物在 77 K 时都显示出磷光。电化学研究表明，peri - acenoacene 框架的 π 延伸引起第一次氧化事件的降低（从 0.83 到 0.40 V），使这些纳米带成为工程化的最佳候选者p型有机半导体。

  DOI：

  10.1021/jacs.2c06803

文献信息

• Rhodium(III)-Catalyzed C-H Vinylation of Arenes: Access to Functionalized Styrenes
  作者：Jun Zhou、Xin Li、Gang Liao、Bing-Feng Shi

  DOI：10.1002/cjoc.201800354

  日期：2018.12

  An effective method has been developed for Rh(III)‐catalyzed direct vinylation of arenes to give functionalized styrenes, using vinyltriethoxysilane as a convenient and inexpensive vinyl source. A wide variety of substrates, including 1‐aryl‐2‐pyrrolidinones, anilines, benzamides and ketones, were compatible with this reaction. Moreover, this method can be applied to the two‐step synthesis of functionalized

  已开发出一种有效的方法，可使用乙烯基三乙氧基硅烷作为方便，廉价的乙烯基来源，对Rh（III）催化的芳烃进行直接乙烯基化，以生成官能化的苯乙烯。此反应兼容多种底物，包括1-芳基-2-吡咯烷酮，苯胺，苯甲酰胺和酮。而且，该方法可以应用于功能化吲哚的两步合成。机理研究表明该反应可能通过氧化性Heck /去甲硅烷基化途径进行。
• Copper-Catalyzed Innate Ethoxycarbon­yldifluoromethylation of Electron-Rich ­Arenes
  作者：Marie-Charlotte Belhomme、Alexandre Bayle、Thomas Poisson、Xavier Pannecoucke

  DOI：10.1002/ejoc.201403656

  日期：2015.3

  the CF2CO2Et moiety into electron-rich arenes. The copper-catalyzed process uses commercially available and inexpensive BrCF2CO2Et as a fluorinated building block. This radical-free reaction proceeds smoothly to give the desired difluoromethylated arenes in modest to good yields with a Friedel–Crafts-type regioselectivity. The direct introduction of α,α-difluoromethylated amides was also investigated

  我们报告了将 CF2CO2Et 部分直接引入富电子芳烃。铜催化工艺使用市售且廉价的 BrCF2CO2Et 作为氟化构件。这种无自由基反应顺利进行，以中等至良好的产率得到所需的二氟甲基化芳烃，并具有 Friedel-Crafts 型区域选择性。还研究了直接引入 α,α-二氟甲基化酰胺，这得到了相应的二氟甲基化芳烃，尽管产率适中。该方法代表了第一个过渡金属催化将官能化氟化部分直接引入富电子芳烃的方法。
• Syntheses and Structures of a Class of Bridged Bis(Amidinate)s and Derivatives
  作者：Fen-Hua Wang、Song Wang、Jiang-Sheng Huang、Jun Zhang、Chun-Mei Ding

  DOI：10.3184/174751918x15260497205682

  日期：2018.6

  pyrrolyl potassium afforded the corresponding derivatives. Their structures were characterised by NMR and HRMS, and some products were further characterised by X-ray crystal structure analysis. It was found that the locations of the hydrogen atoms within the two amidine fragments vary. The structures showed that in the phenylene-linked bis(amidinate)s, the hydrogen atoms were attached to different nitrogen

  已经制备了一系列不同类型的“桥”连接双（脒）。各种连接的二胺与新戊酰氯的反应以非常高的产率产生相应的二酰胺。二酰胺向二亚胺氯化物的转化是在 CH2Cl2 中用 PCl5 实现的。二亚胺氯化物与苯胺或叔丁胺的反应以良好的收率产生双(脒)，而与吡咯钠或2,5-二甲基吡咯钾反应提供相应的衍生物。它们的结构通过NMR和HRMS表征，部分产物通过X射线晶体结构分析进一步表征。发现两个脒片段中氢原子的位置不同。结构表明，在亚苯基连接的双（脒）中，
• A comparative study of the behaviour of N-trimethylsilyl and N-neopentyl-anilines and 1,2-diaminobenzenes towards trimethylalane; X-ray structures of nine Al–N compounds
  作者：Jean-Philippe Bezombes、Barbara Gehrhus、Peter B. Hitchcock、Michael F. Lappert、Philippe G. Merle

  DOI：10.1039/b300957m

  日期：2003.4.17

  The reactions of a pair each of monosubstituted anilines PhNHR1 and disubstituted 1,2-diaminobenzenes C6H4(NHR1)2-1,2 (R1 = SiMe3 = R, or R1 = CH2But = R′) with 1 or 2 equivalents of trimethylalane have been investigated. The trimethylsilyl derivatives were more reactive than the neopentyl analogues. The following crystalline compounds were obtained at ambient temperature or (1) gentle heating: trans-[AlMe2(μ-NRPh)]21, [AlMe3NH(R′)Ph}] 2, [(AlMe2)2μ-(NR)2C6H4-1,2}] 4, [(AlMe2)μ-(NR′)2C6H4-1,2}] 5, [(AlMe)N(R)C6H4NR-μ-1,2}]26 and [AlMe2N(R′(C6H4N(H)R′}] 7, while prolonged heating was required in order to obtain [AlMe2(μ-NR′Ph)]23 and [(AlMeN(R′)C6H4NR′-μ-1,2}]28. The amine adducts 2 and 7, were identified as intermediates to 3 and 8, respectively. Treatment of C6H4(NHR′)2-1,2 with successively 2 LiBun and 2 AlCl3 afforded [AlClN(R′)C6H4NR′-µ-1,2}]29. The diamine adduct [C6H4N(H)R′(AlMe3)}2-1,3] 10 was obtained from C6H4(NHR′)2-1,3 and 2 AlMe3; while the same diamine with successively 2 LiBun, 2 AlClMe2 and 2 tmen yielded a compound tentatively formulated as [C6H4N(R′)AlMe2(tmen)}2-1,3] 11. The X-ray structures of 1–7, 9 and 10 are presented.

  研究了一对单取代苯胺 PhNHR1 和二取代 1,2-二氨基苯 C6H4(NHR1)2-1,2（R1 = SiMe3 = R，或 R1 = CH2But = R²）与1或2当量的三甲基铝的反应。三甲基硅基衍生物的反应性高于新戊基类似物。在常温或(1)轻微加热下，得到以下晶体化合物：trans-[AlMe2(μ-NRPh)]21，[AlMe3NH(R²)Ph}]2，[(AlMe2)2μ-(NR)2C6H4-1,2}]4，[(AlMe2)μ-(NR²)2C6H4-1,2}]5，[(AlMe)N(R)C6H4NR-μ-1,2}]26 和 [AlMe2N(R²)(C6H4N(H)R²}]7，而需要较长时间的加热才能获得 [AlMe2(μ-NR²Ph)]23 和 [(AlMeN(R²)C6H4NR²-μ-1,2}]28。胺加成物2和7被确定为中间体，分别转化为3和8。将C6H4(NHR²)2-1,2依次处理2 LiBun和2 AlCl3得到 [AlClN(R²)C6H4NR²-μ-1,2}]29。从C6H4(NHR²)2-1,3和2 AlMe3得到的二胺加成物为 [C6H4N(H)R²(AlMe3)}2-1,3]10；而同一二胺与依次2 LiBun、2 AlClMe2和2 tmen反应生成一个暂时定为 [C6H4N(R²)AlMe2(tmen)}2-1,3]11 的化合物。展示了1–7、9和10的X射线结构。
• Quantifying chloride binding and salt extraction with poly(methyl methacrylate) copolymers bearing aryl-triazoles as anion receptor side chains
  作者：Kevin P. McDonald、Bo Qiao、Eric B. Twum、Semin Lee、Patrick J. Gamache、Chun-Hsing Chen、Yi Yi、Amar H. Flood

  DOI：10.1039/c4cc03362k

  日期：——

  Copolymers of methyl methacrylate and aryl-triazole based anion receptors were quantitatively analyzed. Transfer of structural features (1 : 1 and 2 : 1 complexes) and Cl− affinities from the parent receptors was demonstrated. Cl−-induced cross-linking changed the polymer's hydrodynamic radius. Extraction of tetrapropylammonium Cl− from water to dichloromethane was enhanced over PMMA.

  对甲基丙烯酸甲酯和芳基三唑阴离子受体的共聚物进行了定量分析。证明了结构特征（1:1和2:1复合物）和母体受体中Cl-亲和力的转移。Cl-诱导的交联改变了聚合物的流体动力学半径。从水中到二氯甲烷的四丙基氯化铵的萃取在PMMA上得到了增强。