cyclopentyl hydroxamic acid | 64214-51-3

• 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: cyclopentyl hydroxamic acid
• 英文别名: N-hydroxycyclopentanecarboxamide
• CAS: 64214-51-3
• 化学式: C₆H₁₁NO₂
• mdl: MFCD09933523
• 分子量: 129.159
• InChiKey: UJWWRLYXVMPKEU-UHFFFAOYSA-N

物化性质

• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.833
• 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：

  cyclopentyl hydroxamic acid 在 nickel(II) perchlorate hexahydrate 、 2,9-二丁基-1,10-邻二氮杂菲 、 频那醇硼烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.67h， 生成 N-(1-(benzylthio)pentan-3-yl)cyclopentanecarboxamide
  参考文献：
  名称：

  1,4,2-二恶唑-5-酮对烯烃进行硫醚导向的NiH催化远程γ-C(sp3)-H加氢酰胺化

  摘要：

  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）。

  DOI：

  10.1021/jacs.1c05834
• 作为产物：
  描述：

  环戊基甲酰氯 在 盐酸羟胺 、 potassium carbonate 作用下， 以 乙醚 、 水 为溶剂， 生成 cyclopentyl hydroxamic acid
  参考文献：
  名称：

  轻度条件下Co（III）催化的含氮杂环与二恶唑酮的CH酰胺化

  摘要：

  公开了在温和条件下使用重氮唑啉作为酰胺化试剂的钴（III）催化的喹啉N-氧化物的C-8选择性C–H酰胺化。该反应以优异的官能团相容性有效地进行。通过克规模合成C-8酰胺喹啉N-氧化物并将该酰胺化产物转化为官能化喹啉，证明了本方法的实用性。此外，开发的催化方法也适用于N-嘧啶二氢吲哚的C-7酰胺化和苯甲酰胺的正酰胺化。

  DOI：

  10.1021/acs.joc.0c01237

文献信息

• 1,2,3-Thiadiazole as a Modifiable and Scalable Directing Group for <i>ortho</i>-C–H Functionalization
  作者：Xiaoyan Jia、Donghui Xing、Jiayi Shen、Bo Li、Yue Zeng、Huanfeng Jiang、Liangbin Huang

  DOI：10.1021/acs.orglett.3c04075

  日期：2024.3.1

  modifiable directing group for C–H amidation and alkynylation with dioxazolones, p-toluenesulfonyl azide, and bromoalkynes in high yield. The densely functionalized 1,2,3-thiadiazole products are modified into thioamide, multisubstituted furan, γ-thiapyrone, thiazole, and various alkynyl sulfides through simple and one-step reactions. The competition experiments reveal that the directing ability of 1,2,3-thiadiazole

  在过去的几十年里，定向C-H键功能化在学术界和工业界具有巨大的应用前景。在 C-H 官能化中，非常需要开发一种新颖的、易于获得的、可扩展的、具有可修改能力的导向基团。在此，我们报道了 1,2,3-噻二唑作为可修饰的导向基团，用于与二恶唑酮、对甲苯磺酰叠氮和溴代炔进行 C-H 酰胺化和炔基化，产率高。通过简单的一步反应，将密集功能化的1,2,3-噻二唑产品改性为硫代酰胺、多取代呋喃、γ-噻吡酮、噻唑和各种炔基硫醚。竞争实验表明，1,2,3-噻二唑的定向能力略弱于吡啶和二齿酰胺，但强于广泛使用的羧酸盐。
• Chemo-enzymatic site-specific modification of peptides and proteins to form cleavable conjugates
  申请人：Northeastern University

  公开号：US11129790B2

  公开（公告）日：2021-09-28

  A method is provided for reversibly modifying a protein or peptide on its glutamine residue(s) by performing a reaction, such as a transglutaminase-catalyzed reaction, between the protein or peptide and an amine-containing reagent, whereby the reagent is linked through its amine function to a side chain of the glutamine residue. Subjecting the modified protein to an appropriate stimulus regenerates the protein or peptide in its original form.

  本发明提供了一种对蛋白质或肽的谷氨酰胺残基进行可逆修饰的方法，该方法是在蛋白质或肽与含胺试剂之间进行反应，如转谷氨酰胺酶催化反应，试剂通过其胺功能与谷氨酰胺残基的侧链相连。将修饰过的蛋白质置于适当的刺激下，蛋白质或肽就会以原来的形式再生。
• Nagarajan; Rajappa; Rajagopalan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 2, p. 222 - 229
  作者：Nagarajan、Rajappa、Rajagopalan、Talwalkar

  DOI：——

  日期：——
• 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.
• Synthesis of cycloalkylhydroxamic acids and their N-substituted derivatives
  作者：Hikmat N. Al-Jallo、Shakir S. Ahmed、Faris I. Saleh、Fatima M. Abbas

  DOI：10.1021/je00025a036

  日期：1981.7