(+/-)-2-N-methylamino-2,3-dimethylbutanamide | 948037-12-5

• 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
• 英文名称: (+/-)-2-N-methylamino-2,3-dimethylbutanamide
• 英文别名: 2,3-Dimethyl-2-(methylamino)butanamide
• CAS: 948037-12-5
• 化学式: C₇H₁₆N₂O
• 分子量: 144.217
• InChiKey: DRXHRWNPGGCPER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-吡啶甲酸 、 (+/-)-2-N-methylamino-2,3-dimethylbutanamide 在 4-二甲氨基吡啶 、 达卡巴嗪 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以58%的产率得到(+/-)-(5-isopropyl-1,5-dimethyl-4,5-dihydro-1H-imidazol-4-on-2-yl)pyridine
  参考文献：
  名称：

  Synthesis of (R)- and (S)-2-N-methylamino-2,3-dimethylbutanamides and (R)- and (S)-(5-isopropyl-1,5-dimethyl-4,5-dihydro-1H-imidazol-4-on-2-yl)pyridines

  摘要：

  Both (R)- and (S)-2-N-methylamino-2,3-dimethylbutanamides have been prepared by the reductive benzylation of (R)- and (S)-2-amino-2,3-dimethylbutanamides, followed by reductive methylation and hydrogenolytic removal of the benzyl group. The reductive benzylation is chemoselective, and not accompanied by dibenzylation even with the application of excess benzaldehyde. Acylation of the (R)- and (S)-2-N-methylamino-2,3-dimethylbutanamides with picolinic acid and subsequent ring closure gave the respective (R)- and (S)-(5-isopropyl-1,5-dimethyl-4,5-dihydro-1H-imidazol-4-on-2-yl)pyridines. Their complexes with Cu(I) catalyze the Kharash-Sosnovsky allylic oxidation with overall yields as high as 99% but with low enantioselectivity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.016
• 作为产物：
  描述：

  (+/-)-2-N-benzyl-N-methylamino-2,3-dimethylbutanamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以94%的产率得到(+/-)-2-N-methylamino-2,3-dimethylbutanamide
  参考文献：
  名称：

  Synthesis of (R)- and (S)-2-N-methylamino-2,3-dimethylbutanamides and (R)- and (S)-(5-isopropyl-1,5-dimethyl-4,5-dihydro-1H-imidazol-4-on-2-yl)pyridines

  摘要：

  Both (R)- and (S)-2-N-methylamino-2,3-dimethylbutanamides have been prepared by the reductive benzylation of (R)- and (S)-2-amino-2,3-dimethylbutanamides, followed by reductive methylation and hydrogenolytic removal of the benzyl group. The reductive benzylation is chemoselective, and not accompanied by dibenzylation even with the application of excess benzaldehyde. Acylation of the (R)- and (S)-2-N-methylamino-2,3-dimethylbutanamides with picolinic acid and subsequent ring closure gave the respective (R)- and (S)-(5-isopropyl-1,5-dimethyl-4,5-dihydro-1H-imidazol-4-on-2-yl)pyridines. Their complexes with Cu(I) catalyze the Kharash-Sosnovsky allylic oxidation with overall yields as high as 99% but with low enantioselectivity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.016

文献信息

• Preparation, 1H and 13C NMR Spectra of Substituted 2-Benzoylaminocarboxamides
  作者：Miloš Sedlák、Aleš Halama、Jaromír Kaválek、Vladimír Macháček、Vojeslav Štěrba

  DOI：10.1135/cccc19950150

  日期：——

  A new type of herbicides based on imidazolinones has been introduced into agriculture under commercial names of Arsenal, Pursuit, Scepter, Assert etc. by American Cyanamid Company since 1983. These compounds destroy diocotyledonous weeds and are almost nontoxic for mammals and fish (LD₅₀ rat - 500 mg/kg, LD₅₀ trout - 300 mg/kg) and nonmutagenic according to the AMES test. The aim of the present work is to synthesize substituted 2-benzoylaminocarboxamides as starting materials for preparation of imidazolinones and potential biologically active substances (Formulae I - III).

  一种基于咪唑啉酮的新型除草剂自1983年起由美国赛诺美公司推出，商业名称为Arsenal、Pursuit、Scepter、Assert等。这些化合物能够消灭双子叶杂草，对哺乳动物和鱼类几乎无毒（LD₅₀ 大鼠 - 500 毫克/千克，LD₅₀ 鳟鱼 - 300 毫克/千克），根据AMES试验结果，这些化合物不具有致突变性。本研究的目的是合成取代的2-苯甲酰氨基羧酰胺，作为制备咪唑啉酮和潜在生物活性物质的起始原料（式 I - III）。
• PHARMACOKINETICALLY IMPROVED COMPOUNDS
  申请人：Surface Logix, Inc.

  公开号：EP1850853A2

  公开（公告）日：2007-11-07
• METHODS OF MAKING PHARMACOKINETICALLY IMPROVED COMPOUNDS COMPRISING FUNCTIONAL RESIDUES OR GROUPS AND PHARMACEUTICAL COMPOSITIONS COMPRISING SAID COMPOUNDS
  申请人：Surface Logix, Inc.

  公开号：EP1848437A2

  公开（公告）日：2007-10-31
• Pharmacokinetically Improved Compounds
  申请人：Campbell Stewart

  公开号：US20080176844A1

  公开（公告）日：2008-07-24

  A compound of formula A having improved non-specific binding characteristics and pharmacokinetic properties is provided: or pharmaceutically acceptable salt, stereoisomer, or hydrate thereof, wherein R 1 is lower alkyl, R 2 and R 3 are independently selected from lower alkyl, and lower alkenyl and lower alkynyl, wherein the lower alkyl, lower alkenyl, and lower alkynyl may be optionally substituted with one or more halogen, lower alkoxy, hydroxy, CN, NO 2 , amino, acylamino, amido, carbonyl, and alkylthio, A is N or C—H, B is N, C—H, C—(SO 2 —R 4 ), or C—CO—R 4 , D is N, C—H, C—(SO 2 —R 4 ) or C—CO—R 4 , E is N or C—H, wherein only one of A, B or E may be N, and one of B or D is C—(SO 2 —R 4 ) or C—CO—R 4 , R 4 is a group having the formula: in which each R 5 , R 6 , R 7 and R 8 are independently selected from H and lower alkyl, wherein the lower alkyl may be optionally substituted with one or more halogen, lower alkoxy, hydroxy, CN, NO 2 , amino, acylamino, amido, carbonyl, and alkylthio; and additionally or alternatively R 6 and R 5 together form a 5- or 6-membered ring, or R 6 and R 7 together form a 3 to 6 membered ring; R 9 is independently selected from H and lower alkyl, wherein the lower alkyl may be optionally substituted with one or more halogen, lower alkoxy, hydroxy, CN, NO 2 , amino, acylamino, amido, carbonyl, and alkylthio; alternatively R 8 and R 9 together with the nitrogen to which they are attached form a 5- or 6-membered ring; n is 1 to 4; and m is 1 to 6.
• Methods of Making Pharmacokinetically Improved Compounds Comprising Functional Residues or Groups and Pharmaceutical Compositions Comprising Said Compounds
  申请人：Campbell Stewart

  公开号：US20110172422A1

  公开（公告）日：2011-07-14

  The present invention relates to methods of modulating the pharmacokinetic and/or pharmacodynamic properties of a compound by attaching at least one functional unit or group to the compound, thereby improving its non-specific binding characteristics and/or pharmacokinetic properties. Compounds comprising at least one functional residue are provided, as are pharmaceutical compositions comprising said compounds.