N-甲基丁酰胺 | 17794-44-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: N-甲基丁酰胺
• 英文名称: N-methylbutyramide
• 英文别名: N-Methyl-butyramid；N-methylbutanamide；N-methylbutyrylamide；N-Methyl-buttersaeureamid
• CAS: 17794-44-4
• 化学式: C₅H₁₁NO
• mdl: MFCD00509177
• 分子量: 101.148
• InChiKey: OLLZXQIFCRIRMH-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111 °C
• 沸点：
  120-123 °C(Press: 22 Torr)
• 密度：
  0.864±0.06 g/cm3(Predicted)
• 保留指数：
  1005

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  7
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-甲基丁酰胺 在 lithium aluminium tetrahydride 作用下， 生成 甲基丁胺
  参考文献：
  名称：

  Long-range anisotropic effects of long chain amides

  摘要：

  DOI：

  10.1007/bf00899784
• 作为产物：
  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

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
• Towards Supramolecular Fixation of NOX Gases: Encapsulated Reagents for Nitrosation
  作者：Yanlong Kang、Grigory V. Zyryanov、Dmitry M. Rudkevich

  DOI：10.1002/chem.200400939

  日期：2005.3.4

  nitrosated with much lower yields (<8 %). Enantiomerically pure encapsulating reagent 2 d was tested for nitrosation of racemic amide 5 t, showing modest but reproducible stereoselectivity and approximately 15 % ee. Given high affinity to NO+ species, which can be generated by a number of NOX gases, these supramolecular reagents and materials may be useful for NOX entrapment and separation in the environment

  已证明在溶液和固态下使用简单的杯[4]芳烃进行化学转化为NO2 / N2O4气体。与这些气体反应后，杯芳烃1在其腔内封入亚硝基（NO +）阳离子，并形成稳定的杯芳烃-NO +络合物2。空穴效应控制着它们的反应性和选择性。配合物2被有效地用于仲酰胺5的亚硝化，包括手性衍生物。观察到独特的尺寸-形状选择性，允许较少拥挤的5-ae N-Me酰胺进行独家亚硝化（产率高达95％）。由于对包封的NO +试剂的阻碍方法，大块的N-Alk（Alk> Me）基材5不反应。制备了坚固的硅胶基杯芳烃材料3，其可逆地捕集到NO2 / N2O4，并形成储存有NO +的硅胶4。对于材料4，对于亚硝化，观察到相似的尺寸-形状选择性。获得N-Me-N-亚硝基衍生物6 d，e的收率约为30％，而将体积较大的酰胺亚硝化的收率要低得多（<8％）。测试了对映体纯的包封试剂2d的消旋酰胺5t的亚硝化，显示适度但可重现的立体选择性和
• Tuning the solid-state emission of the analogous GFP chromophore by varying alkyl chains in the imidazolinone ring
  作者：Xiang Shen、GuangXi Huang、Kan Li、GuanXin Zhang、DeQing Zhang

  DOI：10.1007/s11426-013-4913-x

  日期：2013.9

  New analogues of green fluorescent protein (GFP) chromophore m GFP-C n (n = 1, 3, 5, 11) with alkyl chains of different lengths in the imidazolinone rings were synthesized and their crystal structures were determined. These GFP-like chromophores are all emissive in the solid state. And the solid-state emission quantum yields of increase by extending the lengths of alkyl chains, owing to the fact that the intermolecular pi-pi interactions are significantly weakened based on their crystal structures.

  具有不同长度烷基链的绿色荧光蛋白（GFP）类色素分子GFP-C_n（n = 1, 3, 5, 11）在咪唑啉酮环中被合成，并确定了它们的晶体结构。这些GFP类色素分子在固态下均能发光，并且随着烷基链长度的增加，固态发光量子产率提高，这是由于基于它们晶体结构的分子间π-π相互作用显著减弱所致。
• ATP Regeneration System in Chemoenzymatic Amide Bond Formation with Thermophilic CoA Ligase
  作者：Chloé M. Lelièvre、Mélanie Balandras、Jean‐Louis Petit、Carine Vergne‐Vaxelaire、Anne Zaparucha

  DOI：10.1002/cctc.201901870

  日期：2020.2.20

  counterparts. To limit the use of ATP, we implemented an ATP regeneration system combining polyphosphate kinase 2 (PPK2 Class III) and inorganic pyrophosphatase. Suitability of this system was illustrated by the lab‐scale chemoenzymatic synthesis of N‐methylbutyrylamide in 77 % yield using low enzyme loading and 5 % molar ATP.

  CoA连接酶是通过腺苷酸中间体分两步催化ATP依赖的辅酶A加成到羧酸的酶。该中间体可通过亲核非酶加成胺而转移，以得到用于合成目的的相应酰胺。为此，我们选择了嗜热性CoA连接酶来研究各种羧酸向其酰胺对应物的转化。为了限制ATP的使用，我们实施了一个ATP再生系统，该系统结合了多磷酸激酶2（PPK2 III类）和无机焦磷酸酶。该系统的适用性通过实验室规模的化学酶法合成N-甲基丁酰酰胺，使用低酶负荷和5％摩尔ATP的产率为77％来说明。
• Novel delta dicarbonyl compounds and methods for using same
  申请人：Beacon Laboratories, Inc.

  公开号：EP1216986A2

  公开（公告）日：2002-06-26

  Amidomethyl esters, carbonylmercaptomethyl esters, keto-containing esters, amidomethyl thioesters, amidomethyl amides, and methylene dithioesters are disclosed. The novel compounds have two carbonyl groups connected by a linking moiety having an oxygen, sulfur or nitrogen attached to a methylene group, to which is further attached a sulfur, nitrogen or CH2 group. The use of these compounds in treating illnesses and conditions, such as cancer, hemological disorders, inherited metabolic disorders and others, is also disclosed.

  披露了amidomethyl酯、羰基巯基甲酯、含酮基的酯、amidomethyl硫代酯、amidomethyl酰胺和亚甲基二硫代酯。这些新颖的化合物具有两个羰基团，通过一个连接基团连接，该连接基团具有一个氧、硫或氮连接到一个亚甲基基团，进一步连接到一个硫、氮或CH2基团。还披露了这些化合物在治疗疾病和病症，如癌症、血液疾病、遗传代谢性疾病等方面的用途。