N,N-二甲基环丙胺 | 58862-94-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N,N-二甲基环丙胺
• 英文名称: N,N-dimethylcyclopropanamine
• CAS: 58862-94-5
• 化学式: C₅H₁₁N
• 分子量: 85.149
• InChiKey: DYVUNUQDYHPXSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-二甲基环丙胺 在 双氧水 作用下， 以 水 为溶剂， 生成 Dimethyl-cyclopropyl-amin-oxyd
  参考文献：
  名称：

  Cyclopropene. V. Some Reactions of Cyclopropene¹

  摘要：

  DOI：

  10.1021/ja01509a045
• 作为产物：
  描述：

  环丙甲基酮 在 ammonium acetate 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 120.0h， 生成 N,N-二甲基环丙胺
  参考文献：
  名称：

  6-(Alkylamino)-9-alkylpurines. A New Class of Potential Antipsychotic Agents

  摘要：

  A series of 6-(alkylamino)-9-alkylpurines was synthesized and evaluated for the property of antagonizing the behavioral effects in animals of the dopamine agonist apomorphine. This model for identifying potential antipsychotic agents is based on the hypothesis that agents that antagonize apomorphine-induced aggressive behavior in rats and apomorphine-induced climbing in mice, but that do not block stereotyped behavior, could have an antipsychotic effect in humans without producing extrapyramidal side effects. The antiaggressive-behavior activity of lead compound 1 (6-(dimethylamino)-9-(3-phenylalaninamidobenzyl)-9H-purine) was improved 48-fold with 6-(cyclopropylamino)-9-(cyclopropylmethyl)-2-(trifluoromethyl)-9H-purine (80) (po ED50 of 2 mg/kg), which was obtained through an iterative sequence of structure-activity relationship studies that encompassed evaluation of the effects of structure variations at the purine 9-, 6-, and 2-positions. Potency was enhanced with a 9-cyclopropyl group, the duration of action was improved with the 6-(cyclopropylamino) substituent, potency was further enhanced with an N-formyl prodrug, and an agent with reduced cardiovascular effect emerged with the 2-trifluoromethyl purine 80. This potential antipsychotic agent was not developed further due to undesirable effects on the stomach.

  DOI：

  10.1021/jm960662s

文献信息

• Making Amines Strong Bases:  Thermodynamic Stabilization of Protonated Guests in a Highly-Charged Supramolecular Host¹
  作者：Michael D. Pluth、Robert G. Bergman、Kenneth N. Raymond

  DOI：10.1021/ja072654e

  日期：2007.9.1

  of the protonated amines are then used to calculate the effective basicity of the encapsulated amines. Depending on the nature of the guest, shifts in the effective basicities of the encapsulated amines of up to 4.5 pK(a) units are observed, signifying a substantial stabilization of the protonated form of the guest molecule and effectively making phosphines and amines strong bases.

  由金属-配体相互作用形成的高电荷、含空腔的超分子组装体作为宿主显着改变封装的质子化胺客体的有效碱度。封装的质子化胺和膦客体的范围显示出与受限结合环境一致的大小选择性。(31)P NMR 研究、质谱研究和客体封装的 pH 依赖性证实了封装客体的质子化。使用选择性反转恢复方法测量客体自交换率，发现与客体的大小相关，而不是与客体的碱度相关。来宾自交换的激活参数与已建立的来宾交换机制一致。然后使用质子化胺的结合常数来计算封装胺的有效碱度。根据客体的性质，观察到封装胺的有效碱度变化高达 4.5 pK(a) 单位，这表明客体分子的质子化形式基本稳定，并有效地使膦和胺成为强碱。
• Cyclopropylamines from N,N-Dialkylcarboxamides and Grignard Reagents in the Presence of Titanium Tetraisopropoxide or Methyltitanium Triisopropoxide
  作者：Armin de Meijere、Vladimir Chaplinski、Harald Winsel、Markus Kordes、Björn Stecker、Vesta Gazizova、Andrei I. Savchenko、Roland Boese、Farina Schill née Brackmann

  DOI：10.1002/chem.201001550

  日期：2010.12.10

  Thirty‐three different N,N‐dialkyl‐ and N‐alkyl‐N‐phosphorylalkyl‐substituted carboxamides 9–17 were treated with unsubstituted as well as with 2‐alkyl‐, 2,2‐dialkyl‐, and 3‐alkenyl‐substituted ethylmagnesium bromides 6 in the presence of stoichiometric amounts of titanium tetraisopropoxide or methyltitanium triisopropoxide to furnish substituted cyclopropylamines 20–25 in 20–98 % yield, depending

  三十三个不同Ñ，ñ -二烷基和ñ -烷基- Ñ -phosphorylalkyl取代羧酰胺9 - 17用未取代的治疗以及用2-烷基- ，2,2-二烷基，和3-链烯基取代乙基镁溴化物6中的化学计量的量的四异丙醇钛或三异丙醇methyltitanium到配料取代环丙胺的存在下20 - 25中20-98％的产率，根据与没有取代基（1：1），优（> 25：1）非对映选择性。通常，环丙胺20 – 28的产率更高（高达98％）用甲基异丙醇三异丙醇钛作为钛介质，获得了非对映选择性的损失。在这些条件下，即使二氧戊环保护的酮，卤素取代的和手性的以及非手性的烷氧基烷基取代的羧酰胺也可以转化为相应的取代的环丙胺，以及未取代的苯基，以及各种烷基取代的乙基溴化镁。多种含杂原子的（例如，被卤素，三苯甲基氧基，四氢吡喃氧基取代）的格氏试剂（共62个实例）。在甲基异丙醇钛存在下，用乙基溴化镁将N，N-二甲酰基烷基胺54转
• METHODS FOR INHIBITING CONVERSION OF CHOLINE TO TRIMETHYLAMINE (TMA)
  申请人：The Procter & Gamble Company

  公开号：US20190099389A1

  公开（公告）日：2019-04-04

  A method of inhibiting the conversion of choline to trimethylamine (TMA) and lowering TMAO in an individual by providing a composition comprising a compound set forth in Formula (I):

  通过提供包含式(I)中所列化合物的组合物，抑制胆碱转化为三甲胺（TMA）并降低个体体内的TMAO的方法。
• Chaplinski, Vladimir; Meijere, Armin de, Angewandte Chemie, 1996, vol. 108, # 4, p. 491 - 492
  作者：Chaplinski, Vladimir、Meijere, Armin de

  DOI：——

  日期：——
• Methylation of Cycloalkanamines with Dimethyl Carbonate in the Presence of Binder-Free NaY Zeolite
  作者：R. I. Khusnutdinov、N. A. Shchadneva、Yu. Yu. Mayakova、T. M. Egorova、A. N. Khazipova、B. I. Kutepov

  DOI：10.1134/s1070428018040231

  日期：2018.4

  N-Methyl- and N,N-dimethylcycloalkanamines were synthesized by reaction of cycloalkanamines with dimethyl carbonate in the presence of NaY zeolite containing no binder. Optimal reactant and catalyst ratios and reaction conditions were found.