1-Cyclobutanecarbohydroxamic acid | 77317-97-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-Cyclobutanecarbohydroxamic acid
• 英文别名: cyclobutyl hydroxamic acid；N-hydroxycyclobutanecarboxamide
• CAS: 77317-97-6
• 化学式: C₅H₉NO₂
• mdl: MFCD09936752
• 分子量: 115.132
• InChiKey: PUYLKDICZHTKBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Cyclobutanecarbohydroxamic acid 在 乙酸酐 、 potassium carbonate 、 盐酸 作用下， 以 乙腈 、 水 为溶剂， 反应 24.0h， 生成 环丁基胺
  参考文献：
  名称：

  在温和条件下由催化量的活化剂诱导的自传播洛森重排

  摘要：

  已经开发了在中等至高极性有机溶剂中由催化量的活化剂引起的温和的自蔓延的洛森重排。在催化量（0.01当量）的乙酸酐和等摩尔量的碱（如干燥的碳酸钾）的存在下，芳族和脂族异羟肟酸的重排可以高收率得到相应的胺。传统Lossen重排的替代方法为从游离异羟肟酸合成胺提供了一种简单温和的方法。

  DOI：

  10.1016/j.tetlet.2014.12.084
• 作为产物：
  描述：

  环丁基甲酰氯 在 羟胺 、 碳酸氢钠 作用下， 以 乙醚 、 水 为溶剂， 反应 2.0h， 以30%的产率得到1-Cyclobutanecarbohydroxamic acid
  参考文献：
  名称：

  环烷基异羟肟酸及其N-取代衍生物的合成

  摘要：

  DOI：

  10.1021/je00025a036

文献信息

• One-pot synthesis of primary amines from carboxylic acids through rearrangement of in situ generated hydroxamic acid derivatives
  作者：Yujiro Hoshino、Naoya Ohtsuka、Takuya Okada、Kiyoshi Honda

  DOI：10.1016/j.tetlet.2016.10.037

  日期：2016.11

  primary amines from carboxylic acids through a Lossen rearrangement of hydroxamic acid derivatives, which were in situ generated by the reaction of carboxylic acids with O-trimethylsilylhydroxylamine (NH2OTMS) and carbonyl diimidazole (CDI, 1.5 equiv) in dimethyl sulfoxide at room temperature, has been achieved. This one-pot method could be applied to various carboxylic acids such as aromatic, heteroaromatic

  通过羟肟酸衍生物的Lossen重排由羧酸一锅合成伯胺，羟肟酸的羧酸与O-三甲基甲硅烷基羟胺（NH 2 OTMS）和羰基二咪唑（CDI，1.5当量）的反应原位生成。已经达到室温下的二甲基亚砜。这种一锅法可以应用于各种羧酸，例如芳族，杂芳族，脂族和旋光性底物。
• Thioether-Directed NiH-Catalyzed Remote γ-C(sp³)–H Hydroamidation of Alkenes by 1,4,2-Dioxazol-5-ones
  作者：Bingnan Du、Yuxin Ouyang、Qishu Chen、Wing-Yiu Yu

  DOI：10.1021/jacs.1c05834

  日期：2021.9.22

  amidation of unactivated alkenes. Due to the preference for five-membered nickelacycle formation, the chain-walking isomerization initiated by the NiH insertion to an alkene can be terminated at the γ-methylene site remote from the alkene moiety. By employing 2,9-dibutyl-1,10-phenanthroline (L4) as the ligand and dioxazolones as the reagent, the amidation occurs at the γ-C(sp3)–H bonds to afford the amide

  开发了一种 NiH 催化的硫醚导向的环金属化策略，以实现未活化烯烃的远程亚甲基 C-H 键酰胺化。由于优先形成五元镍环，由 NiH 插入烯烃引发的链式异构化可以在远离烯烃部分的 γ-亚甲基位点终止。通过使用 2,9-二丁基-1,10-菲咯啉 ( L4 ) 作为配体和二恶唑酮作为试剂，酰胺化发生在 γ-C(sp 3 )-H 键上，以提供高达 90% 的酰胺产物产量（> 40 个例子）具有显着的区域选择性（高达 24:1 rr）。
• Redox-active cytotoxic diorganotin(IV) cycloalkylhydroxamate complexes with different ring sizes: Reduction behaviour and theoretical interpretation
  作者：Xianmei Shang、Elisabete C.B.A. Alegria、M. Fátima C. Guedes da Silva、Maxim L. Kuznetsov、Qingshan Li、Armando J.L. Pombeiro

  DOI：10.1016/j.jinorgbio.2012.08.019

  日期：2012.12

  Two series of new diorganotin(IV) cycloalkylhydroxamate complexes with different ring sizes (cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl), formulated as the mononuclear [R2Sn(HL)(2)] (1:2) (a, R=Bu-n and Ph) and the polymeric [R2SnL](n) (1:1) (b, R=Bu-n) compounds, were prepared and fully characterized. Single crystal X-ray diffraction for [(Bu2Sn)-Bu-nC5H9C(O)NHO}(2)] (3a) discloses the cis geometry and strong intermolecular NH center dot center dot center dot O interactions. The in vitro cytotoxic activities of the complexes were evaluated against HL-60, Bel-7402, BGC-823 and KB human tumour cell lines, the greater activity concerning [(Bu2Sn)-Bu-n(HL)(2)] [HL=C3H5C(O)NHO (1a), C6H11C(O)NHO (4a)] towards BGC-823. The complexes undergo, by cyclic voltammetry and controlled-potential electrolysis, one irreversible overall two-electron cathodic process at a reduction potential that does not appear to correlate with the antitumour activity. The electrochemical behaviour of [R2Sn(C5H9C(O)NHO)(2)] [R=Bu-n (3a), Ph (7a)] was also investigated using density functional theory (DFT) methods, showing that the ultimate complex structure and the mechanism of its formation are R dependent: for the aromatic (R = Ph) complex, the initial reduction step is centred on the phenyl ligands and at the metal, being followed by a second reduction with Sn-O and Sn-C ruptures, whereas for the alkyl (R=Bu-n) complex the first reduction step is centred on one of the hydroxamate ligands and is followed by a second reduction with Sn-O bond cleavages and preservation of the alkyl ligands. In both cases, the final complexes are highly coordinative unsaturated Sn-II species with the cis geometry, features that can be of biological significance. (C) 2012 Elsevier Inc. All rights reserved.
• Ethylene biosynthesis. 12. Analog approach to the active site topography of the ethylene-forming enzyme. Novel hydroxamate inhibitors
  作者：Michael C. Pirrung、Jun Cao、Jrlung Chen

  DOI：10.1021/jo00123a012

  日期：1995.9

  In order to understand both the substrate specificity and active site topography of the ethylene-forming enzyme (EFE), a number of analogs of its substrate, 1-aminocyclopropanecarboxylic acid, have been prepared and studied as inhibitors. Because of the dependence of EFE activity on iron, hydroxamic acids, a functional group known to bind iron tightly, derived from several small carboxylic/amino acids were studied along with the parent amino acids. The activity of these materials was assayed in vitro against the purified EFE from apple fruit. The varying potency of the amino acid hydroxamates suggests that they do not act simply by binding to iron and removing it from the enzyme. The order of their potency was consistent with the idea that binding reflects both metal chelation and hydrophobic interactions in the active site. The most potent inhibitor, ACC-hydroxamate, has about 1 mu M K-i.
• Self-propagated Lossen rearrangement induced by a catalytic amount of activating agents under mild conditions
  作者：Yujiro Hoshino、Yuki Shimbo、Naoya Ohtsuka、Kiyoshi Honda

  DOI：10.1016/j.tetlet.2014.12.084

  日期：2015.1

  self-propagated Lossen rearrangement induced by a catalytic amount of activating agents in medium to high polar organic solvents has been developed. The rearrangement of aromatic and aliphatic hydroxamic acids in the presence of a catalytic amount (0.01 equiv) of acetic anhydride and an equimolar amount of base such as well-dried potassium carbonate afforded the corresponding amines in high yields.

  已经开发了在中等至高极性有机溶剂中由催化量的活化剂引起的温和的自蔓延的洛森重排。在催化量（0.01当量）的乙酸酐和等摩尔量的碱（如干燥的碳酸钾）的存在下，芳族和脂族异羟肟酸的重排可以高收率得到相应的胺。传统Lossen重排的替代方法为从游离异羟肟酸合成胺提供了一种简单温和的方法。