N-苄基-N-环丙基环丙胺 | 246257-67-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-苄基-N-环丙基环丙胺
• 英文名称: Benzyldicyclopropylamine
• 英文别名: N-Benzyl-N-cyclopropylcyclopropanamine
• CAS: 246257-67-0
• 化学式: C₁₃H₁₇N
• 分子量: 187.285
• InChiKey: NMQCJEFVOVIFAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 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-苄基-N-环丙基环丙胺 在 palladium on activated charcoal titanium(IV) isopropylate 、 sodium hydroxide 、 四丁基氯化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 氯仿 、 水 为溶剂， 20.0~40.0 ℃ 、101.33 kPa 条件下， 反应 14.0h， 生成 二环丙胺
  参考文献：
  名称：

  Radical Cations of Trialkylamines:  ESR Spectra and Structures

  摘要：

  Novel syntheses of cyclopropyldiisopropylamine (15), di-tert-butylcyclopropylamine (16), dicyclopropylisopropylamine (17), and tricyclopropylamine (18) are described. Hyperfine data were determined by ESR spectroscopy for the radical cations of these trialkylamines, as well as for those of ethyldiisopropylamine (10), diisopropyl-n-propylamine (11), dicyclohexylethylamine (12), diisopropyl-3-pentylamine (14), and 1-azabicyclo[3.3.3]undecane (manxine; 27). The radical cation of triisopropylamine (13) was reexamined under conditions of improved spectral resolution. Coupling constants of the N-14 nucleus and the beta-protons in the radical cations of 18 trialkylamines provide reliable information about the geometries of these species, which are confirmed by theoretical calculations. With the exception of a few oligocyclic amines, for which flattening is impaired by the rigid molecular framework, all of the radical cations should be planar. Correlation between the observed coupling constants of the beta-protons and the calculated values of the dihedral angle theta, defining the conformation of the alkyl substituent or the azacycloalkane, is verified. Upon oxidation, striking changes occur for those amines that have cyclopropyl substituents, because of the tendency of these groups to assume a perpendicular conformation in the neutral amines and a bisected orientation in the corresponding radical cations.

  DOI：

  10.1021/jo990458n
• 作为产物：
  描述：

  溴甲苯 在 METHYLTITANIUM TRIISOPROPOXIDE 、 sodium methylate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 16.0h， 生成 N-苄基-N-环丙基环丙胺
  参考文献：
  名称：

  四异丙醇钛或三异丙醇甲基钛存在下的N，N-二烷基羧酰胺和格氏试剂中的环丙胺

  摘要：

  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

  DOI：

  10.1002/chem.201001550

文献信息

• AMINOPYRAZOLE AMIDE DERIVATIVE
  申请人：Horiuchi Yoshihiro

  公开号：US20110071289A1

  公开（公告）日：2011-03-24

  Disclosed is a compound represented by the formula (1) below or a pharmaceutically acceptable salt thereof, which is useful as an agent for prevention and/or treatment of diabetes and the like. (In the formula, R A and R B independently represent an optionally substituted alkyl group or the like; R C represents an optionally substituted alkyl group or the like; R D represents a hydrogen atom or the like; R E represents a hydrogen atom or the like; and R F represents a group selected from those represented by the formulae (G1) below: wherein one hydrogen atom serves as a bonding hand, or the like.)

  本发明涉及一种化合物，其化学式如下（1），或其药学上可接受的盐，可用作预防和/或治疗糖尿病等疾病的药剂。（在公式中，RA和RB分别独立表示可选取代的烷基或类似物；RC表示可选取代的烷基或类似物；RD表示氢原子或类似物；RE表示氢原子或类似物；RF表示从以下式（G1）中选取的基团：其中一个氢原子作为结合手或类似物。）
• Radical Cations of Trialkylamines:  ESR Spectra and Structures
  作者：Armin de Meijere、Vladimir Chaplinski、Fabian Gerson、Pascal Merstetter、Edwin Haselbach

  DOI：10.1021/jo990458n

  日期：1999.9.1

  Novel syntheses of cyclopropyldiisopropylamine (15), di-tert-butylcyclopropylamine (16), dicyclopropylisopropylamine (17), and tricyclopropylamine (18) are described. Hyperfine data were determined by ESR spectroscopy for the radical cations of these trialkylamines, as well as for those of ethyldiisopropylamine (10), diisopropyl-n-propylamine (11), dicyclohexylethylamine (12), diisopropyl-3-pentylamine (14), and 1-azabicyclo[3.3.3]undecane (manxine; 27). The radical cation of triisopropylamine (13) was reexamined under conditions of improved spectral resolution. Coupling constants of the N-14 nucleus and the beta-protons in the radical cations of 18 trialkylamines provide reliable information about the geometries of these species, which are confirmed by theoretical calculations. With the exception of a few oligocyclic amines, for which flattening is impaired by the rigid molecular framework, all of the radical cations should be planar. Correlation between the observed coupling constants of the beta-protons and the calculated values of the dihedral angle theta, defining the conformation of the alkyl substituent or the azacycloalkane, is verified. Upon oxidation, striking changes occur for those amines that have cyclopropyl substituents, because of the tendency of these groups to assume a perpendicular conformation in the neutral amines and a bisected orientation in the corresponding radical cations.
• 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
• Tricyclopropylamine and Its Radical Cation
  作者：Armin de Meijere、Vladimir Chaplinski、Harald Winsel、Mikhael A. Kusnetsov、Paul Rademacher、Roland Boese、Thomas Haumann、Marit Traetteberg、Paul von R. Schleyer、Tosja Zywietz、Haijun Jiao、Pascal Merstetter、Fabian Gerson

  DOI：10.1002/(sici)1521-3773(19990816)38:16<2430::aid-anie2430>3.0.co;2-v

  日期：1999.8.16

  A surprisingly high first vertical ionization energy (8.44 eV) and an unusually high oxidation potential are exibited by tricyclopropylamine (1)-in sharp contrast to triisopropylamine. These are attributed to the near-tetrahedral geometry of 1 at the N atom and the perpendicular orientation-with respect to the N-orbital axis-of the cyclopropyl groups. gamma-Irradiation of 1 led to the radical cation 1(.)(+), which, in accord with computations, has a planar C(3h)-symmetrical structure. The EPR-spectroscopic and computational results disclose a dramatic, previously not reported, conformational change on going from 1 to 1(.)(+).