N-(4-Chlorophenyl)-1,1,1-trimethylsilanamine | 63911-86-4

• 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-(4-Chlorophenyl)-1,1,1-trimethylsilanamine
• 英文别名: 4-chloro-N-trimethylsilylaniline
• CAS: 63911-86-4
• 化学式: C₉H₁₄ClNSi
• 分子量: 199.755
• InChiKey: KHYFCLHLSFESKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(4-Chlorophenyl)-1,1,1-trimethylsilanamine 在 正丁基锂 、 二氧化硫 作用下， 生成 N-亚磺酰-4-氯苯胺
  参考文献：
  名称：

  A New Synthesis ofN-Sulfinylamines by Sulfinylation ofN-Trimethylsilylamines using Sulfur Dioxide

  摘要：

  DOI：

  10.1055/s-1981-29451
• 作为产物：
  描述：

  对氯苯胺 、 三甲基硅烷基二乙胺 生成 N-(4-Chlorophenyl)-1,1,1-trimethylsilanamine
  参考文献：
  名称：

  Kaufmann, Klaus-Dieter; Gisbier, Doris; Ruehlmann, Klaus, Zeitschrift fur Chemie, 1981, vol. 21, # 4, p. 141 - 142

  摘要：

  DOI：

文献信息

• P4VPy–CuO nanoparticles as a novel and reusable catalyst: application at the protection of alcohols, phenols and amines
  作者：Farhad Shirini、Abdollah Fallah-Shojaei、Masoumeh Abedini、Laleh Samavi

  DOI：10.1007/s13738-016-0887-x

  日期：2016.9

  P4VPy–CuO nanoparticles were synthesized using ultrasound irradiations. Relevant properties of the synthesized nanoparticles were investigated by X-ray diffraction, scanning electron microscopy, transmission electron microscopy and Fourier transform infrared spectroscopy. After identification, the prepared reagent was used for the promotion of different types of protection reactions of alcohols, phenols and amines. Easy workup, short reaction times, excellent yields, relatively low cost and reusability of the catalyst are the striking features of the reported methods.

  采用了超声波辐照法合成了P4VPy–CuO纳米粒子。通过X射线衍射、扫描电子显微镜、透射电子显微镜和傅里叶变换红外光谱对合成的纳米粒子的相关性质进行了研究。在鉴定之后，制备的试剂被用于促进不同类型的醇、酚和胺的保护反应。操作简便、反应时间短、产率高、成本相对较低以及催化剂的重复使用性是所报道方法的显著特点。
• Stoichiometric Reactions of CO₂ and Indium-Silylamides and Catalytic Synthesis of Ureas
  作者：Maotong Xu、Andrew R. Jupp、Douglas W. Stephan

  DOI：10.1002/anie.201708921

  日期：2017.11.6

  4, Cl 5). 0.05–2.0 mol % of the species 3 acts as a pre‐catalyst for the conversion of aryl and alkyl silylamines under CO2 (2–3 atm) to give the corresponding ureas in 70–99 % yields. A proposed mechanism is supported by experimental and computational data.

  铟化合物在（N（森达3）2）2 Cl⋅THF（2）和在（N（森达3）2）氯2 ⋅（THF）Ñ（3）显示出与CO反应2，得到[（箱3的Si）2 N）INX（μ-OSiMe 3）] 2（X = N（森达3）2 4，氯5）。0.05–2.0 mol％的物种3充当在CO 2下转化芳基和烷基甲硅烷基胺的预催化剂（2-3 atm），以70-99％的产率得到相应的尿素。实验和计算数据支持了所提出的机制。
• Synthesis of Urea Derivatives from CO ₂ and Silylamines
  作者：Maotong Xu、Andrew R. Jupp、Maegan S. E. Ong、Katherine I. Burton、Saurabh S. Chitnis、Douglas W. Stephan

  DOI：10.1002/anie.201900058

  日期：2019.4.16

  A series of thirty‐three N,N′‐diaryl, dialkyl, and alkyl‐aryl ureas have been prepared in pyridine or toluene by reaction of silylamines with CO2. This protocol is shown to provide facile access to 13C‐labeled ureas, as well as chiral and macrocyclic ureas. These reactions proceed through initial generation of the corresponding silylcarbamates, which subsequently react with silylamine under thermal

  通过使甲硅烷基胺与CO 2反应，在吡啶或甲苯中制备了33种N，N'-二芳基，二烷基和烷基芳基尿素。已显示该协议可轻松访问13 C标记的尿素以及手性和大环脲。这些反应通过首先产生相应的甲硅烷基氨基甲酸酯来进行，随后在热条件下与甲硅烷基胺反应，以提供热力学上有利的脲和二甲硅烷基醚。
• Generation of thionitrosoarenes (ArNS) from N-(arylaminothio)phthalimides and in situ trapping with alkenes and conjugated dienes
  作者：Martin R. Bryce、Paul C. Taylor

  DOI：10.1039/p19900003225

  日期：——

  species (8). Derivatives (8a–h) have been trapped in good yield as their Diels–Alder adducts [e.g. N-aryl-1,2-thiazine derivatives (9) and (10)] with the following conjugated dienes: butadiene, 2,3-dimethylbutadiene, 1,4-diphenylbutadiene, (E,E)- and (E,Z)-hexa-2,4-diene, 1,1′-bicyclopentenyl (25) and 1,1′-bicyclohexenyl (26). The stereochemistry of the diene is retained in the adducts (19)–(24). Thionitrosoarene

  通过邻苯二甲酰亚胺磺酰氯与适当的芳基胺的三甲基甲硅烷基衍生物反应制得了一系列N-（芳基氨基硫代）邻苯二甲酰亚胺衍生物（7a - h）。在室温下用三乙胺处理时，化合物（7）碎裂，得到瞬态硫代亚硝基物质（8）。衍生物（8a - h）的Diels-Alder加合物[例如N-芳基-1,2-噻嗪衍生物（9）和（10）]与以下共轭二烯被捕获，收率高：丁二烯，2,3-二甲基丁二烯，1,4-二苯基丁二烯（E，E）-和（E，Z）-六-2,4-二烯，1,1'-双环戊烯基（25）和1,1'-双环己烯基（26）。二烯的立体化学保留在加合物（19）–（24）中。硫代亚硝基芳烃衍生物（8）还通过向二甲基丁二烯，异丁烯和α-甲基苯乙烯中加烯而得到亚磺酰胺衍生物，例如（11）和（12）-（16）。N- Aryliminosulphur dichloride（34）与2,3-二甲基丁二烯反应生成1,2-噻嗪和次磺酰胺产物，可能是通过硫代亚硝基芳烃中间体。
• N,N’‐Diaryl‐Sulfurdiimides are Strongly Redox Tuned
  作者：Nathan D. D. Hill、René T. Boeré

  DOI：10.1002/chem.202400563

  日期：——

  The synthesis and extensive characterization of nine aryl sulfur diimides (SDIs, Ar−NSN−Ar) are presented with a robust computational and experimental investigation of the fundamental properties of these important members of the thiazyl family of compounds, with particular attention paid to their highly tunable electrochemical behaviour. This is the first work to undertake a systematic comparison of the electrochemical profiles of a coherent series of SDIs to demonstrate and quantify the response of their reduction potentials to substituent electron‐donating and ‐withdrawing properties. This effect is found to be not only exceptionally strong, but also correlates very closely with computed orbital energies. Electron paramagnetic resonance spectroscopy is used to determine the nature, localization, and qualitative lifetimes of the radical anions of SDIs. This work also addresses significant misconceptions about physical properties of SDIs. Experimental data and modern computational methods are employed to provide a resolute answer to the long‐standing contention of the solution‐state conformations of SDIs, and to correct historical mistakes in the assignment of infrared spectroscopic data. High‐quality crystal structures of all SDIs in this work showcase the utility of the recently introduced structural refinement software NoSpherA2, enabling full anisotropic refinement of H‐atoms with accurate C−H bond lengths.

  摘要 本文介绍了九种芳基硫二亚胺（SDIs，Ar-NSN-Ar）的合成和广泛表征，并对这些噻唑族化合物重要成员的基本性质进行了深入的计算和实验研究，尤其关注它们高度可调的电化学行为。这是首次对一系列连贯的 SDI 的电化学特性进行系统比较，以展示和量化它们的还原电位对取代基电子供取特性的响应。研究发现，这种效应不仅异常强烈，而且与计算出的轨道能量密切相关。电子顺磁共振光谱法用于确定 SDIs 自由基阴离子的性质、定位和定性寿命。这项研究还解决了有关 SDI 物理性质的重大误解。通过实验数据和现代计算方法，对 SDIs 溶液态构象的长期争论给出了明确的答案，并纠正了红外光谱数据赋值方面的历史性错误。这项研究中所有 SDIs 的高质量晶体结构都展示了最近推出的结构细化软件 NoSpherA2 的实用性，该软件可以对具有精确 C-H 键长度的 H 原子进行完全各向异性细化。