N-Allyl-N-methyl-1-amino-2-propanone | 150630-79-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-Allyl-N-methyl-1-amino-2-propanone
• 英文别名: 1-(allyl(methyl)amino)propan-2-one；1-(allyl(methyl)amino)propan-2-oneN-methylallylamine；1-[Methyl(prop-2-enyl)amino]propan-2-one
• CAS: 150630-79-8
• 化学式: C₇H₁₃NO
• 分子量: 127.186
• InChiKey: VLIALFTWPPDGJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Allyl-N-methyl-1-amino-2-propanone 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 水 、 甲苯 为溶剂， 反应 3.0h， 以71%的产率得到N-Allyl-N-methyl-1-amino-2-propanone (E/Z)-oxime
  参考文献：
  名称：

  Stereochemistry. 82. Conformation of fused five-membered heterocyclic rings derived from the intramolecular oxime olefin cycloaddition reaction

  摘要：

  Thermal intramolecular oxime olefin cycloaddition Of alpha-allylamino aldoximes and ketoximes 4 led stereospecifically to formation of oxadiazabicyclo[3.3.0]octanes 6. The presence of heteroatoms in these bicyclic fused 5-membered rings permits for the first time an evaluation of the conformation of this system by means of NMR. We found that some substituents in 6 restrict the conformational mobility of these five-membered rings to the extent that only one conformer was detected at 20-degrees-C. In other cases an equilibrium between two major conformers was revealed by NMR. Equilibrium measurements indicated a free energy of conversion of 13.2-13.4 kcal/mol, apparently a manifestation of the N-inversion in the isoxazolidine ring. NMR studies also showed that the NH-proton in isoxazolidines 6 prefers an axial orientation. Empirical force field data were adjusted for MM calculations in these bicyclic heterocycles. The MM2 force field with AMBER charge gave the best fit between calculated and experimental coupling constants.

  DOI：

  10.1021/jo00069a011
• 作为产物：
  描述：

  N-甲基烯丙基胺 、 溴丙酮 以 二氯甲烷 为溶剂， 反应 0.17h， 以95%的产率得到N-Allyl-N-methyl-1-amino-2-propanone
  参考文献：
  名称：

  Stereochemistry. 82. Conformation of fused five-membered heterocyclic rings derived from the intramolecular oxime olefin cycloaddition reaction

  摘要：

  Thermal intramolecular oxime olefin cycloaddition Of alpha-allylamino aldoximes and ketoximes 4 led stereospecifically to formation of oxadiazabicyclo[3.3.0]octanes 6. The presence of heteroatoms in these bicyclic fused 5-membered rings permits for the first time an evaluation of the conformation of this system by means of NMR. We found that some substituents in 6 restrict the conformational mobility of these five-membered rings to the extent that only one conformer was detected at 20-degrees-C. In other cases an equilibrium between two major conformers was revealed by NMR. Equilibrium measurements indicated a free energy of conversion of 13.2-13.4 kcal/mol, apparently a manifestation of the N-inversion in the isoxazolidine ring. NMR studies also showed that the NH-proton in isoxazolidines 6 prefers an axial orientation. Empirical force field data were adjusted for MM calculations in these bicyclic heterocycles. The MM2 force field with AMBER charge gave the best fit between calculated and experimental coupling constants.

  DOI：

  10.1021/jo00069a011

文献信息

• Aryne-Mediated [2,3]-Sigmatropic Rearrangement of Tertiary Allylic Amines
  作者：Juan Zhang、Zhi-Xiong Chen、Ting Du、Bing Li、Yonghong Gu、Shi-Kai Tian

  DOI：10.1021/acs.orglett.6b02344

  日期：2016.10.7

  3]-sigmatropic rearrangement of quaternary allylic ammonium ylides via in situ activation of tertiary allylic amines with arynes under mild conditions. Using 2-(trimethylsilyl)aryl triflates as aryne precursors, a range of tertiary allylic amines bearing electron-withdrawing groups underwent [2,3]-sigmatropic rearrangement to furnish structurally diverse homoallylic amines in moderate to good yields. The reaction

  已经建立了通过在温和条件下用芳烃原位活化叔烯丙基胺来[4,3]-σ重排季铵烯丙基铵的新策略。使用2-（三甲基甲硅烷基）芳基三氟甲磺酸酯作为芳烃前体，对一系列带有吸电子基团的叔烯丙基胺进行[2,3]-σ重排，以中等至良好的收率提供结构多样的均胺。该反应能够构建具有出色对映体纯度的四级立体中心和具有极高非对映选择性的官能化环丙烷。
• Accumulation, Characterization and Reactivity of Chiral Ammonium‐Carboxonium Dications in Superacid
  作者：Emanuela Berrino、Thomas Cantin、Maxime Artault、Stefanie Beck、Christoph Jessen、Jérôme Marrot、Frédéric Guégan、Agnès Mingot、Andreas Kornath、Sébastien Thibaudeau

  DOI：10.1002/anie.202404066

  日期：——

  Chiral ammonium-oxocarbenium dications are accumulated in superacid through a tandem diastereoselective proton-transfer/intramolecular cyclization. Their reactivity in the diastereoselective remote functionalization of non-activated alkene is explored.

  手性铵-氧碳鎓阳离子通过串联非对映选择性质子转移/分子内环化在超强酸中积累。探讨了它们在非活化烯烃的非对映选择性远程官能化中的反应性。
• PEPTIDOMIMETIC MACROCYCLES
  申请人：Aileron Therapeutics, Inc.

  公开号：US20130123169A1

  公开（公告）日：2013-05-16

  The present invention provides peptidomimetic macrocycles capable of modulating growth hormone levels and methods of using such macrocycles for the treatment of disease.
• US20140256638A1
  申请人：——

  公开号：US20140256638A1

  公开（公告）日：2014-09-11
• US20140256639A1
  申请人：——

  公开号：US20140256639A1

  公开（公告）日：2014-09-11