N-methyl-N-(2-bromobenzoyl)hydroxylamine | 63977-16-2

• 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-methyl-N-(2-bromobenzoyl)hydroxylamine
• 英文别名: N-methyl o-bromobenzohydroxamic-acid；2-Brom-N-methylbenzohydroxamsaeure；N-methyl o-bromobenzohydroxamic acid；2-bromo-N-hydroxy-N-methylbenzamide
• CAS: 63977-16-2
• 化学式: C₈H₈BrNO₂
• 分子量: 230.061
• InChiKey: FMYSGAZXGXPDEG-UHFFFAOYSA-N

物化性质

• 沸点：
  339.1±44.0 °C(Predicted)
• 密度：
  1.621±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methyl-N-(2-bromobenzoyl)hydroxylamine 生成 (Z)-[(2-bromophenyl)-hydroxymethylidene]-hydroxy-methylazanium
  参考文献：
  名称：

  LOBO, A. M.;PRABHAKAR, S.;TAVARES, M. R., TETRAHEDRON LETT., 1981, 22, N 31, 3007-3008

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴苯甲酰氯 、 N-甲基羟胺盐酸盐 在 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 生成 N-methyl-N-(2-bromobenzoyl)hydroxylamine
  参考文献：
  名称：

  Photocatalytic C(sp3)‐H gem‐Difluoroallylation and Alkylation with Alkenes via a Base‐Assisted Formal 1,2‐Hydrogen Atom Transfer of Amidyl Radicals

  摘要：

  Comprehensive SummaryCompared to well‐established 1,5‐HAT of N‐centered radicals, the synthetic applications of 1,2‐HAT process were scarce due to the high barrier and constrained three‐membered transition state. Here, we have developed a novel C(sp3)‐H gem‐difluoroallylation via a base assisted formal 1,2‐HAT of amidyl radicals with the reductive quenching cycle of photocatalyst. This transformation enables the efficient formation of α‐aminoalkyl radicals via 1,2‐HAT and showcases good functional group tolerance. Our preliminary mechanistic experiments, along with Density Functional Theory (DFT) calculations demonstrate the feasibility of 1,2‐HAT of amidyl radicals, especially when assisted by a base. Furthermore, our method also succeeds in the Giese addition of electron‐deficient alkenes as well as styrene.

  DOI：

  10.1002/cjoc.202400122

文献信息

• 一种含吡啶羟胺类化合物、制备方法及其用途
  申请人：中国科学院上海有机化学研究所

  公开号：CN103992304B

  公开（公告）日：2016-09-14

  本发明是一种含吡啶羟胺类化合物，制备方法以及用途。其结构通式如下：在结构通式(I)中：R1选自C1‑C4烷基；R2选自C3‑C6环烷基、取代苯基、取代杂环基；X选自氢、三氟甲基或卤素。主要用于农用杀菌剂。
• Spectral Characterization and Crystal Structures of Two Newly Synthesized Ligands of N-Methyl O-Substituted Benzohydroxamic Acids
  作者：Khan Naqeebullah、Yang Farina、Lo Kong Mun、Nor Fadilah Rajab、Normah Awang

  DOI：10.1007/s10870-013-0469-z

  日期：2013.11

  Two new derivatives of hydroxamic acid having the general formula RC(O)N(RN)OH (R = alkyl/aryl; RN = alkyl/aryl or H), have been synthesized by the condensation method in an ice-bath. The compounds, N-methyl o-iodobenzohydroxamic acid and N-methyl o-bromobenzohydroxamic acid have been isolated as crystalline solids, stable in air and soluble in organic solvents and in aqueous alcohol solution. A systematic investigation of the derivatives were carried out both in solid and in solution. They have been structurally characterized by elemental analysis, and the results were in good agreement with the values calculated for the proposed formula. These derivatives were further investigated on the basis of FT-IR, multinuclear 1H, 13C NMR spectroscopy, and Single Crystal X-ray crystallographic studies, indicating that both the compounds are structurally similar. Two new compounds of hydroxamic acid have been synthesized by condensation method and were structurally characterized by elemental analysis, FT-IR, multinuclear 1H, 13C NMR spectroscopy, and Single Crystal X-ray crystallographic studies. Figure 3 Thermal ellipsoidal plot of C8 H8 Br N O2. Displacement ellipsoids are drawn at the 50 % probability level, and H atoms are shown as spheres of arbitrary radii.

  在冰浴中通过缩合法合成了两种羟肟酸的新衍生物，其通式为 RC(O)N(RN)OH （R = 烷基/芳基；RN = 烷基/芳基或 H）。分离出的 N-甲基邻碘苯甲酰羟肟酸和 N-甲基邻溴苯甲酰羟肟酸化合物为结晶固体，在空气中稳定，可溶于有机溶剂和乙醇水溶液。对这些衍生物的固体和溶液进行了系统研究。通过元素分析对这些衍生物进行了结构鉴定，结果与根据拟议公式计算得出的数值十分吻合。根据傅立叶变换红外光谱、多核 1H、13C NMR 光谱和单晶 X 射线晶体学研究对这些衍生物进行了进一步研究，结果表明这两种化合物在结构上相似。通过缩合法合成了两种新的羟肟酸化合物，并通过元素分析、傅立叶变换红外光谱、多核 1H、13C NMR 光谱和单晶 X 射线晶体学研究确定了其结构特征。图 3 C8 H8 Br N O2 的热椭球图。位移椭球体以 50 % 的概率水平绘制，H 原子以任意半径的球体表示。
• Triorganotin(IV) complexes with o-substituted arylhydroxamates: Synthesis, spectroscopic characterization, X-ray structures and in vitro cytotoxic activities
  作者：Naqeebullah Khan、Yang Farina、Lo Kong Mun、Nor Fadilah Rajab、Normah Awang

  DOI：10.1016/j.jorganchem.2014.04.015

  日期：2014.8

  Six new triorganotin(IV) complexes with six different RN-2-X-benzohydroxamic acid ligands having general formula R'C(O)N(RN)OH (R' = alkyl/aryl; RN = alkyl/aryl or H), (X = -I, -NO2, -OCH3, -Br and R = -CH3, -C6H5 and -C6H4-CH3), were prepared by condensation method with the respective organotin(IV) chlorides using a stoichiometric ratio of 1:1. The bonding and coordination behaviour of these complexes were investigated on the basis of FT-IR, multinuclear H-1, C-13 and Sn-119 NMR spectroscopies. Complexes (1) and (3) crystallize in the orthorhombic P2(1)2(1)2(1) space group and complex (2) crystallizes in the triclinic P-1 space group whereas complex (4) crystallizes in the monoclinic P2(1)/c space group. The tested triphenyltin(IV) complexes showed significant cytotoxicities, higher than doxorubicin toward K-562, Jurkat, HepG2 and L929 cells. (C) 2014 Elsevier B.V. All rights reserved.
• Kalinin, V. N., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 5, p. 936 - 939
  作者：Kalinin, V. N.

  DOI：——

  日期：——