N-甲基丁酰氧肟酸 | 65753-90-4

• 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: N-甲基丁酰氧肟酸
• 英文名称: N-methylbutyrohydroxamic acid
• 英文别名: N-methyl-N-hydroxybutyramide；N-Methyl butyrohydroxamic acid；N-hydroxy-N-methylbutanamide
• CAS: 65753-90-4
• 化学式: C₅H₁₁NO₂
• 分子量: 117.148
• InChiKey: DJQAPXOHSUIFSU-UHFFFAOYSA-N

物化性质

• 沸点：
  184.7±23.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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-甲基丁酰氧肟酸 在 乙醇 、 ruthenium(III) trichloride hydrate 、 zinc/copper couple 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 36.0h， 生成 N-甲基丁酰胺
  参考文献：
  名称：

  Ruthenium-catalyzed reduction of N-alkoxy- and N-hydroxyamides

  摘要：

  A ruthenium-catalyzed reduction of N-alkoxy- and N-hydroxyamides was found to afford corresponding amides in good to high yields. A simple RuCl3/Zn-Cu/alcohol system, without the addition of any other ligands, exhibited a high catalytic activity, and therefore the present reaction does not require a stoichiometric amount of metals or metal complexes as reductants. When beta-substituted-alpha,beta-unsaturated N-methoxyamides were employed as substrates, concurrent hydrogenation of the olefin moiety proceeded slowly with deprotection of the methoxy group. In the reduction of N-hydroxyamides, the alcoholic solvent was found to function as a hydrogen donor. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2011.08.026
• 作为产物：
  描述：

  N-甲基羟胺盐酸盐 、 丁酰氯 在 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 生成 N-甲基丁酰氧肟酸
  参考文献：
  名称：

  使用亲电氮自由基光诱导酰胺和胺的远程官能化

  摘要：

  远端位置的 C(sp 3 )−H 键与官能团的选择性官能化是合成化学中的一项具有挑战性的任务。这里报道了一种用于酰胺和受保护胺的不同官能化的光诱导自由基级联策略。该过程基于亲电酰胺自由基的氧化生成以及随后通过 1,5-H 原子转移进行的转位，从而实现远程氟化、氯化，并首次实现硫醚化、氰化和炔基化。该过程能够容纳最常见的功能组，并提供可以进一步详细说明的有用构建块。通过氨基酸和二肽的后期功能化证明了该策略的实用性。

  DOI：

  10.1002/anie.201807941

文献信息

• Lawesson's reagent for direct thionation of hydroxamic acids: Substituent effects on LR reactivity
  作者：Witold Przychodzeń

  DOI：10.1002/hc.20259

  日期：——

  To explore the generality and scope of direct thionation of hydroxamic acids (HAs), the reaction of various structurally diverse HAs with Lawesson's reagent was investigated. The yield of thiohydroxamic acid (THAs) is poor when HAs possess bulky acyl and/or N-substituents, acidic α-hydrogen atoms, or an N-phenyl ring. THAs yields were correlated with Brown sigma parameter. The relative rates of two

  为了探索异羟肟酸 (HA) 直接硫化的一般性和范围，研究了各种结构不同的 HA 与劳森试剂的反应。当 HA 具有庞大的酰基和/或 N-取代基、酸性 α-氢原子或 N-苯环时，硫代异羟肟酸 (THA) 的产率很低。THA 产量与 Brown sigma 参数相关。还测量了两个后续过程 k 和 k 的相对速率。还发现了 N-异丙基苯并硫代异羟肟酸的次甲基质子化学位移的相关性。© 2006 Wiley Periodicals, Inc. 杂原子化学 17:676–684, 2006; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20259
• Ruthenium-catalyzed reduction of N-alkoxy- and N-hydroxyamides
  作者：Hiroko Fukuzawa、Yasuyuki Ura、Yasutaka Kataoka

  DOI：10.1016/j.jorganchem.2011.08.026

  日期：2011.11

  A ruthenium-catalyzed reduction of N-alkoxy- and N-hydroxyamides was found to afford corresponding amides in good to high yields. A simple RuCl3/Zn-Cu/alcohol system, without the addition of any other ligands, exhibited a high catalytic activity, and therefore the present reaction does not require a stoichiometric amount of metals or metal complexes as reductants. When beta-substituted-alpha,beta-unsaturated N-methoxyamides were employed as substrates, concurrent hydrogenation of the olefin moiety proceeded slowly with deprotection of the methoxy group. In the reduction of N-hydroxyamides, the alcoholic solvent was found to function as a hydrogen donor. (C) 2011 Elsevier B.V. All rights reserved.
• Photoinduced Remote Functionalization of Amides and Amines Using Electrophilic Nitrogen Radicals
  作者：Sara P. Morcillo、Elizabeth M. Dauncey、Ji Hye Kim、James J. Douglas、Nadeem S. Sheikh、Daniele Leonori

  DOI：10.1002/anie.201807941

  日期：2018.9.24

  here is a photoinduced radical cascade strategy for the divergent functionalization of amides and protected amines. The process is based on the oxidative generation of electrophilic amidyl radicals and their subsequent transposition by 1,5‐H‐atom transfer, resulting in remote fluorination, chlorination and, for the first time, thioetherification, cyanation, and alkynylation. The process is tolerant

  远端位置的 C(sp 3 )−H 键与官能团的选择性官能化是合成化学中的一项具有挑战性的任务。这里报道了一种用于酰胺和受保护胺的不同官能化的光诱导自由基级联策略。该过程基于亲电酰胺自由基的氧化生成以及随后通过 1,5-H 原子转移进行的转位，从而实现远程氟化、氯化，并首次实现硫醚化、氰化和炔基化。该过程能够容纳最常见的功能组，并提供可以进一步详细说明的有用构建块。通过氨基酸和二肽的后期功能化证明了该策略的实用性。