N¹,N²-di(naphthalen-1-yl)ethylenediamine | 75188-96-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N¹,N²-di(naphthalen-1-yl)ethylenediamine
• 英文别名: N,N'-bis(naphthalen-1-yl)ethane-1,2-diamine；N1,N2-di(naphthalen-1-yl)ethylenediamine；N,N'-Di-1-naphthylethylendiamin；1,2-bis(1-naphthylamino)ethane；1,2-di(1-naphthylamino)ethane；N.N'-Dinaphthyl-aethylendiamin；N,N'-dinaphthalen-1-ylethane-1,2-diamine
• CAS: 75188-96-4
• 化学式: C₂₂H₂₀N₂
• 分子量: 312.414
• InChiKey: UJUVJLIDMVCMDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N¹,N²-di(naphthalen-1-yl)ethylenediamine 在 三乙胺 、 间氯过氧苯甲酸 、 三氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 68.0h， 生成 1,3-di(1-naphthyl)-2-piperidino-1,3,2-diazaphospholidine 2-oxide
  参考文献：
  名称：

  酮三氯甲硅烷基烯醇酸酯的手性磷酸酰胺催化的醛醇缩合。机械方面

  摘要：

  已经研究了将三氯甲硅烷基烯酸酯催化，对映选择性加成到醛的机理。使用ReactIR和快速注入NMR（RINMR）光谱进行的动力学研究已证实，涉及一个或两个与硅离子组织中心结合的磷酰胺的双机理途径的同时运行。最初基于催化剂负载量研究和非线性效应研究假定了这种机械二分法。这种二元性解释了各种类型的磷酰胺的反应性和立体选择性的差异。Arrhenius激活参数的确定表明，醛醇的添加是通过可逆的方式发生的，尽管不利的是形成了活化的复合物，并且自然丰度1313 C NMR动力学同位素效应（KIE）研究已经确定，周转限制步骤是添加羟醛。对一系列磷酰胺的彻底检查已经建立了经验结构-活性选择性关系。此外，已经研究了催化剂负载量，添加速率，溶剂和添加剂的影响，这些影响共同形成了醇醛添加的统一机理图。

  DOI：

  10.1021/jo060243v
• 作为产物：
  描述：

  对甲苯磺酰氯 在 calcium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 N¹,N²-di(naphthalen-1-yl)ethylenediamine
  参考文献：
  名称：

  KR2017/125601

  摘要：

  公开号：

文献信息

• A New Class of Stable, Saturated N‐Heterocyclic Carbenes with <i>N</i> ‐Naphthyl Substituents: Synthesis, Dynamic Behavior, and Catalytic Potential
  作者：Ludovic Vieille‐Petit、Xinjun Luan、Ronaldo Mariz、Sascha Blumentritt、Anthony Linden、Reto Dorta

  DOI：10.1002/ejic.200900010

  日期：2009.5

  comprised of substituted naphthyl units. This generates C2-symmetric (anti) and Cs-symmetric (syn) atropisomers. The interconversion between the isomers is studied in detail both for the N-heterocyclic carbene salts and the free carbenes through variable-temperature 1H NMR spectroscopic studies; activation free energies are calculated and can be linked to the substitution pattern of the naphthyl moieties

  已经合成了一个新的易于获得且稳定的咪唑啉-2-亚基，其中侧链由取代的萘基单元组成。这会生成 C2 对称（反）和 Cs 对称（syn）阻转异构体。通过变温 1H NMR 光谱研究，详细研究了 N-杂环卡宾盐和游离卡宾的异构体之间的相互转化；计算活化自由能并且可以将其与萘基部分的取代模式相关联。合成了包含新 N-杂环卡宾的钯配合物，初步数据表明这些化合物在芳基溴和芳基氯的 Buchwald-Hartwig 胺化反应中作为预催化剂表现良好。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Synthesis of Phosphoramides for the Lewis Base-Catalyzed Allylation and Aldol Addition Reactions
  作者：Scott E. Denmark、Xiping Su、Yutaka Nishigaichi、Diane M. Coe、Ken-Tsung Wong、Stephen B. D. Winter、Jun Young Choi

  DOI：10.1021/jo9820723

  日期：1999.3.1

  Both chiral and achiral phosphoramides of diverse structure were prepared from diamines by the coupling to phosphorus(V) or phosphorus(III) reagents. Several enantiopure 1,2-diphenyl-1,2-ethanediamine analogues have been prepared by the reductive coupling of the corresponding N-silylimine with NbCl(4)(THF)(2) and subsequent resolution by the formation of diastereomeric menthyl carbamates. (S,S)-N,

  通过与磷（V）或磷（III）试剂偶联，由二胺制备了多种结构的手性和非手性磷酰胺。几种对映体纯的1,2-二苯基-1,2-乙二胺类似物是通过将相应的N-硅酰亚胺与NbCl（4）（THF）（2）还原偶联而制备的，随后通过形成非对映异构的氨基甲酸薄荷酯进行拆分。（S，S）-N，N′-二-（1-萘基）-1,2-二苯基-1,2-乙二胺15是通过（S，S）-1,2-二苯基-1的芳基化制备的，2-乙二胺与碘化萘。
• Identification and Characterization of a New Family of Catalytically Highly Active Imidazolin-2-ylidenes
  作者：Xinjun Luan、Ronaldo Mariz、Michele Gatti、Chiara Costabile、Albert Poater、Luigi Cavallo、Anthony Linden、Reto Dorta

  DOI：10.1021/ja800861p

  日期：2008.5.1

  A new class of easily accessible and stable imidazolin-2-ylidenes has been synthesized where the side chains are comprised of substituted naphthyl units. Introduction of the naphthyl groups generates C-2-symmetric (rac) and C-s-symmetric (meso) atropisomers, and interconversion between the isomers is studied in detail both experimentally and computationally. Complete characterization of the carbenes includes rare examples of crystallographically characterized saturated NHC structures. Steric properties of the ligands and an investigation of their stability are also presented. In catalysis, the new ligands show versatility comparable to the most widely used NHCs IMes/SIMes or IPr/SIPr. Excellent catalytic results are obtained when either the NHC salts (ring-opening alkylation of epoxides), NHC-modified palladium compounds (C-C and C-N cross-couplings), or NHC-ruthenium complexes (ring-closing metathesis, RCM) are employed. In several cases, this new ligand family provides catalytic systems of higher reactivity than that observed with previously reported NHC compounds.
• Synthesis and Characterization of Novel Triarylmethane-Based Dyes for Thermally Stable Blue Color Filters
  作者：Chan Gyu Lee、Jeong Yong Park、Young II Park、Seo-Hyun Jung、Gyu Sung Lee、Jong Mok Park、Do-Hoon Hwang、Hoyoul Kong

  DOI：10.1166/jnn.2019.16682

  日期：2019.8.1

  Two new triarylmethane-based dye molecules with a dimeric structure, TAM-1 and TAM-2, were designed and synthesized as potential blue color filter materials for liquid-crystal displays. The dimeric structure of TAM-1 was designed to improve the thermal stability of a well-known blue dye, Victoria Blue BO. TAM-2 was designed to further improve the solubility of TAM-1 by introducing long alkyl ester groups. The synthesized dyes TAM-1 and TAM-2 were transmissive in the wavelength range of 410-460 nm and showed good thermal stability with 5% weight degradation temperatures (T-5d) of 259 degrees C and 289 C, respectively, and less than 1% of weight loss at 230 degrees C. Moreover, TAM-2 showed excellent solubility (20.1 wt%) as opposed to Victoria Blue BO (0.03 wt%) and TAM-1 (3.5 wt%) in PGMEA.
• Schoenberg, Alexander; Singer, Erich; Eckert, Philipp, Chemische Berichte, 1980, vol. 113, # 8, p. 2823 - 2826
  作者：Schoenberg, Alexander、Singer, Erich、Eckert, Philipp

  DOI：——

  日期：——