环丙烷羧肟酸 | 5687-86-5

• 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
• 中文名称: 环丙烷羧肟酸
• 英文名称: cyclopropane carbohydroxamic acid
• 英文别名: 1-Cyclopropanecarbohydroxamic acid；N-hydroxycyclopropanecarboxamide；cyclopropanecarbohydroxamic acid；cyclopropyl hydroxamic acid；Cyclopropan-carbhydroxamsaeure；Cyclopropancarbohydroxamsaeure
• CAS: 5687-86-5
• 化学式: C₄H₇NO₂
• mdl: MFCD09937478
• 分子量: 101.105
• InChiKey: VIHDBAIWGYSTFR-UHFFFAOYSA-N

物化性质

• 熔点：
  124 °C (decomp)(Solv: ethyl acetate (141-78-6))
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  环丙烷羧肟酸 、 二正丁基氧化锡 以 氘代甲醇-d 、 苯 为溶剂， 反应 6.0h， 以54%的产率得到
  参考文献：
  名称：

  Redox-active cytotoxic diorganotin(IV) cycloalkylhydroxamate complexes with different ring sizes: Reduction behaviour and theoretical interpretation

  摘要：

  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-n{C5H9C(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.

  DOI：

  10.1016/j.jinorgbio.2012.08.019
• 作为产物：
  描述：

  环丙基甲酰氯 在 盐酸羟胺 、 potassium carbonate 作用下， 以 乙醚 、 水 为溶剂， 生成 环丙烷羧肟酸
  参考文献：
  名称：

  Rh(III) 催化的双重不对称 CH 烯基化环化/酰胺化反应能够提供多种呋喃喹唑啉酮类化合物

  摘要：

  多官能化芳烃是众多生物活性天然产物和药物中不可替代的一部分。过渡金属催化的直接不对称双或多CH键官能化是非常可取的，但探索较少。在此，我们开发了一种 Rh(III) 催化的不对称 C H 烯基化环化/酰胺化反应与带有O的烯烃系链芳烃的反应，能够在一个步骤中提供多种呋喃喹唑啉酮，具有广泛的底物范围和良好的官能团耐受性。

  DOI：

  10.1016/j.tetlet.2022.154141

文献信息

• N-((Alkylamino)carbonyl)-N-(((alkylamino)carbonyl)oxy)acylamides with
  申请人：The Dow Chemical Company

  公开号：US04413009A1

  公开（公告）日：1983-11-01

  The present invention is directed to N-((alkylamino)carbonyl)-N-(((alkylamino)carbonyl)oxy)acylamides and their use in inhibiting the growth of HeLa cells, P.sub.388 leukemia or MX-1 carcinomas in mammals.

  本发明涉及N-((烷基氨基甲酰基)-N-((烷基氨基甲酰基)氧基)酰胺及其在抑制哺乳动物中HeLa细胞、P.sub.388白血病或MX-1癌瘤生长中的应用。
• Ir-Catalyzed Intermolecular Branch-Selective Allylic C–H Amidation of Unactivated Terminal Olefins
  作者：Honghui Lei、Tomislav Rovis

  DOI：10.1021/jacs.9b00237

  日期：2019.2.13

  An efficient method for intermolecular branch-selective allylic C-H amidation has been accomplished via Ir(III) catalysis. The reaction proceeds through initial allylic C-H activation, supported by the isolation and crystallographic characterization of an allyl-Ir(III) intermediate, followed by a subsequent oxidative amidation with readily available dioxazolones as nitrenoid precursors. A diverse range

  通过 Ir(III) 催化实现了一种有效的分子间分支选择性烯丙基 CH 酰胺化方法。该反应通过最初的烯丙基 CH 活化进行，由烯丙基-Ir(III) 中间体的分离和晶体学表征支持，然后用易于获得的二恶唑酮作为氮烯类前体进行氧化酰胺化。多种酰胺以良好的产率和区域选择性成功安装在末端烯烃的支链位置。重要的是，该反应允许使用酰胺衍生的类氮烯前体，避免有问题的 Curtius 型重排。
• Photoorganocatalytic One-Pot Synthesis of Hydroxamic Acids from Aldehydes
  作者：Giorgos N. Papadopoulos、Christoforos G. Kokotos

  DOI：10.1002/chem.201600333

  日期：2016.5.10

  An efficient one‐pot synthesis of hydroxamic acids from aldehydes and hydroxylamine is described. A fast, visible‐light‐mediated metal‐free hydroacylation of dialkyl azodicarboxylates was used to develop the subsequent addition of hydroxylamine hydrochloride. A range of aliphatic and aromatic aldehydes were employed in this reaction to give hydroxamic acids in high to excellent yields. Application

  描述了一种有效的一锅法从醛和羟胺合成异羟肟酸的方法。快速，可见光介导的偶氮二羧酸二烷基酯的无金属加氢酰化反应用于随后添加盐酸羟胺的过程。在该反应中使用了一系列脂族和芳族醛，以高产率或优异产率得到异羟肟酸。在抗癌药伏立诺他的合成中证明了当前方法的应用。
• 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：——
• Jones; Scott, Journal of the American Chemical Society, 1922, vol. 44, p. 415
  作者：Jones、Scott

  DOI：——

  日期：——