2,2,2-trichloroethyl cyclohexylsulfamate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 氨基磺酸衍生物
• 英文名称: 2,2,2-trichloroethyl cyclohexylsulfamate
• 英文别名: N-(cyclohexyl)-2,2,2-trichloroethoxysulfonamide；2,2,2-trichloroethyl N-cyclohexylsulfamate
• 化学式: C₈H₁₄Cl₃NO₃S
• 分子量: 310.629
• InChiKey: DPTPWJINJWZSEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  环己烷 、 氨基磺酸-2,2,2-三氯乙酯 在 碘苯二乙酸 、 C₃₂H₄₄ClN₄O₄Rh₂*3CH₂Cl₂ 作用下， 反应 3.0h， 以100%的产率得到2,2,2-trichloroethyl cyclohexylsulfamate
  参考文献：
  名称：

  Introducing a mixed-valent dirhodium(ii,iii) catalyst with increased stability in C–H amination

  摘要：

  报道了一种新的混价Rh2II,III二聚体[Rh2(espn)2Cl]（espn2- = α,α,α′,α′-四甲基-1,3-苯二丙酸酰胺）。该化合物在溶液中以低浓度易于解离Cl-，形成活性[Rh2(espn)2]+催化剂，该催化剂进行的分子内C–H氨基化反应的TON超过1400。这项工作将Rh2II,III二聚体的研究范围扩展到亚硝基化学。

  DOI：

  10.1039/c2cc36614b

文献信息

• [RuIV(F20-TPP)Cl2] efficiently catalysed inter- and intra-molecular nitrene insertion into sp3 C–H bonds of hydrocarbons using phosphoryl azides as nitrene sources
  作者：Wenbo Xiao、Jinhu Wei、Cong-Ying Zhou、Chi-Ming Che

  DOI：10.1039/c3cc41110a

  日期：——

  [Ru(IV)(F20-TPP)Cl2][H2(F20-TPP) = meso-tetrakis(pentafluorophenyl)porphyrin] is an active catalyst for both inter- and intra-molecular nitrene insertion into sp(3) C-H bonds of hydrocarbons in good to high product yields using phosphoryl azides as nitrene sources.

  [Ru（IV）（F20-TPP）Cl2] [H2（F20-TPP）=内消旋四（五氟苯基）卟啉]是将分子间和分子内氮插入到sp（3）CH键中的活性催化剂使用磷酰基叠氮化物作为氮源，可以产生高至高产率的碳氢化合物。
• Metal-free C–H amination of unactivated hydrocarbons with sulfonylimino-λ³-bromanes generated in situ from (diacetoxybromo)benzene
  作者：Kazunori Miyamoto、Taiga Ota、Md. Mahbubul Hoque、Masahito Ochiai

  DOI：10.1039/c4ob02160f

  日期：——

  A simple method for direct metal-free C–H amination of unactivated hydrocarbons using easy-handling diacetoxy-λ³-bromane and triflylamide or sulfamate esters was developed.

  一种简单的方法，利用易处理的二乙酰氧基-λ3-溴烷和三氟乙酰胺酯或磺酸酯，直接对未活化的碳氢化合物进行无金属C-H氨基化反应。
• Rhodium-catalyzed intermolecular C(sp³)–H amination in a purely aqueous system
  作者：Xunbo Lu、Yufeng Shi、Fangrui Zhong

  DOI：10.1039/c7gc03149a

  日期：——

  An efficient Rh-catalyzed intermolecular C(sp3)–H amination in a purely aqueous system is developed for the first time. This methodology features environmental benignity, broad substrate scope and versatility in late-stage functionalization of several biologically important molecules. Such an oxidation protocol provides easy access to various aliphatic amine derivatives in an efficient and sustainable

  首次开发了在纯水体系中有效的Rh催化的分子间C（sp 3）–H胺化反应。该方法具有环境友好性，广泛的底物范围和多种生物学上重要分子的后期功能化功能。这样的氧化方案提供了以有效和可持续的方式容易地获得各种脂族胺衍生物的途径。
• Catalytic Intermolecular Amination of C−H Bonds: Method Development and Mechanistic Insights
  作者：Kristin Williams Fiori、J. Du Bois

  DOI：10.1021/ja0650450

  日期：2007.1.1

  y Reaction methodology for intermolecular C-H amination of benzylic and 3 degrees C-H bonds is described. This process uses the starting alkane as the limiting reagent, gives optically pure tetrasubstituted amines through stereospecific insertion into enantiomeric 3 degrees centers, displays high chemoselectivity for benzylic oxidation, and enables the facile preparation of isotopically enriched N-15-labeled compounds. Access to substituted amines, amino alcohols, and diamines is thereby made possible in a single transformation. Important information relevant to understanding the initial steps in the catalytic cycle, reaction chemoselectivity, the nature of the active oxidant, and pathways for catalyst inactivation has been gained through mechanistic analysis; these studies are also presented.
• <i>O</i>- and <i>N</i>-Sulfations of Carbohydrates Using Sulfuryl Imidazolium Salts
  作者：Laura J. Ingram、Ahmed Desoky、Ahmed M. Ali、Scott D. Taylor

  DOI：10.1021/jo9014112

  日期：2009.9.4

  A series of sulfuryl imidazolium salts (SISs) were prepared and examined as reagents for incorporating trichloroethyl-protected sulfate esters into carbohydrates. The SIS that contained a 1,2-dimethylimidazolium moiety (SIS 9) proved to be a superior sulfating compared to SISs bearing no alkyl groups or bulkier alkyl groups on the imidazolium ring. Difficult O-sulfations that required prolonged reaction times and a large excess of the SIS bearing a 1-methylimidazolium group (SIS 5) were achieved in high yield using less than half the amount of SIS 9 in less time. Certain N-sulfated compounds that were practically inaccessible using SIS 5 were obtained in excellent yield using SIS 9.