N-allylcyclopropanamine | 1085180-77-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-allylcyclopropanamine
• 英文别名: allylcyclopropylamine；N-(prop-2-en-1-yl)cyclopropanamine；N-prop-2-enylcyclopropanamine
• CAS: 1085180-77-3
• 化学式: C₆H₁₁N
• mdl: MFCD16472270
• 分子量: 97.16
• InChiKey: DSZJHTGYRGFVKI-UHFFFAOYSA-N

物化性质

• 沸点：
  126.2±9.0 °C(Predicted)
• 密度：
  0.86±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-allylcyclopropanamine 在 盐酸 作用下， 以 2-甲基四氢呋喃 、 甲基叔丁基醚 、 异丙醇 为溶剂， 反应 4.67h， 生成 N-allyldicyclopropylamine hydrochloride
  参考文献：
  名称：

  The Development of Scalable and Efficient Methods for the Preparation of Dicyclopropylamine HCl Salt

  摘要：

  The unique chemical properties of dicyclopropylamine (DCPA) 1 render its synthesis a challenge for process chemists despite its structural simplicity. Chemical instability and high aqueous solubility further complicate the process for DCPA's preparation, isolation, and purification. In this note we describe the development of three strategies for the synthesis of DCPA 1, all of which provide material with excellent purity profiles (>99 GC area 96). Our final route provides significant improvements in terms of cost-efficiency, safety, scalability, and impurity content. Highlights of this strategy include two chemo-selective, Pd-catalyzed, deallylation reactions and an efficient reductive amination protocol. To circumvent the chemical instability of DCPA 1, an innovative isolation procedure was developed which reliably reduced the amount of Pd residue to less than 20 ppm. Following this protocol, impurities such as N-propylcyclopropyl-, mono-cyclopropyl-, and N-ethyl-cyclopropylamines (3, 4, and 17) were minimized to 0.06, not detectable, and 0.02%, respectively.

  DOI：

  10.1021/op2000755
• 作为产物：
  描述：

  diallylcyclopropylamine 在 bis(η3-allyl-μ-chloropalladium(II)) 、 硫代水杨酸 、 1,4-双(二苯基膦)丁烷 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-allylcyclopropanamine
  参考文献：
  名称：

  The Development of Scalable and Efficient Methods for the Preparation of Dicyclopropylamine HCl Salt

  摘要：

  The unique chemical properties of dicyclopropylamine (DCPA) 1 render its synthesis a challenge for process chemists despite its structural simplicity. Chemical instability and high aqueous solubility further complicate the process for DCPA's preparation, isolation, and purification. In this note we describe the development of three strategies for the synthesis of DCPA 1, all of which provide material with excellent purity profiles (>99 GC area 96). Our final route provides significant improvements in terms of cost-efficiency, safety, scalability, and impurity content. Highlights of this strategy include two chemo-selective, Pd-catalyzed, deallylation reactions and an efficient reductive amination protocol. To circumvent the chemical instability of DCPA 1, an innovative isolation procedure was developed which reliably reduced the amount of Pd residue to less than 20 ppm. Following this protocol, impurities such as N-propylcyclopropyl-, mono-cyclopropyl-, and N-ethyl-cyclopropylamines (3, 4, and 17) were minimized to 0.06, not detectable, and 0.02%, respectively.

  DOI：

  10.1021/op2000755

文献信息

• Reversal of polarity by catalytic SET oxidation: synthesis of azabicyclo[<i>m</i>.<i>n</i>.0]alkanes <i>via</i> chemoselective reduction of amidines
  作者：Kirana Devarahosahalli Veeranna、Kanak Kanti Das、Sundarababu Baskaran

  DOI：10.1039/d1ob00416f

  日期：——

  A one-pot catalytic method has been developed for the stereoselective synthesis of cyclopropane-fused cyclic amidines using CuBr2/K2S2O8 as an efficient single electron transfer (SET) oxidative system. The generality of this mild method is demonstrated with a wide variety of substrates to furnish pharmaceutically important amidines containing aza-bicyclic and novel aza-tricyclic frameworks in very

  使用CuBr 2 /K 2 S 2 O 8作为有效的单电子转移（SET）氧化体系，开发了一种用于立体选择性合成环丙烷稠合环脒的单锅催化方法。这种温和方法的普遍性通过多种底物得到证明，以非常好的收率提供含有氮杂-双环和新型氮杂-三环骨架的药学上重要的脒。将环脒化学选择性还原为 2-/3-氮杂双环[ m . n .0]烷烃和八氢吲哚已使用 NaBH 4 /I 2开发试剂系统。化学选择性还原脒官能团的合成范围已在基于亚氨基糖的 (±)-表喹酰胺类似物的立体选择性合成中得到例证。
• Studies on a series of milnacipran analogs containing a heteroaromatic group as potent norepinephrine and serotonin transporter inhibitors
  作者：Troy Vickers、Brian Dyck、Junko Tamiya、Mingzhu Zhang、Florence Jovic、Jonathan Grey、Beth A. Fleck、Anna Aparicio、Michael Johns、Liping Jin、Hui Tang、Alan C. Foster、Chen Chen

  DOI：10.1016/j.bmcl.2008.04.045

  日期：2008.6

  A series of milnacipran analogs containing a heteroaromatic group were synthesized and studied as monoamine transporter inhibitors. Many compounds exhibited higher potency than milnacipran at NET and NET/SERT with no significant change in lipophilicity. For example, compound R-26f was about 10-fold more potent than milnacipran with IC(50) values of 8.7 and 26 nM at NET and SERT, respectively. (C) 2008 Elsevier Ltd. All rights reserved.
• Characterization of Thien-2-yl 1<i>S</i>,2<i>R</i>-Milnacipran Analogues as Potent Norepinephrine/Serotonin Transporter Inhibitors for the Treatment of Neuropathic Pain
  作者：Brian Dyck、Junko Tamiya、Florence Jovic、Rebecca R. Pick、Margaret J. Bradbury、Julie O’Brien、Jenny Wen、Michael Johns、Ajay Madan、Beth A. Fleck、Alan C. Foster、Binfeng Li、Mingzhu Zhang、Joe A. Tran、Troy Vickers、Jonathan Grey、John Saunders、Chen Chen

  DOI：10.1021/jm8009537

  日期：2008.11.27

  Thien-2-yl 1S,2R-milnacipran analogues were synthesized and characterized as norepinephrine/serotonin transporter inhibitors. These compounds possessed higher potencies than IS,2R-milnacipran (2R-1) while maintaining low molecular weight and moderate lipophilicity, which are the important features for the pharmacological and pharmacokinetic characteristics of milnacipran (1). Thus, compound 5c exhibited IC50 values of 2.3 and 32 nM, respectively, at NET and SERT, which were more than 10-fold better than those of 1 (NET IC50 = 77 nM, SERT IC50 = 420 nM). Moreover, 5c achieved the same efficacy as 1, but with much lower doses, in a rodent spinal nerve ligation pain model. In addition, 5c displayed desirable pharmacokinetic properties in several species, including high oral availability and significant brain penetration.
• The Development of Scalable and Efficient Methods for the Preparation of Dicyclopropylamine HCl Salt
  作者：Ke Chen、Martin D. Eastgate、Bin Zheng、Jun Li

  DOI：10.1021/op2000755

  日期：2011.7.15

  The unique chemical properties of dicyclopropylamine (DCPA) 1 render its synthesis a challenge for process chemists despite its structural simplicity. Chemical instability and high aqueous solubility further complicate the process for DCPA's preparation, isolation, and purification. In this note we describe the development of three strategies for the synthesis of DCPA 1, all of which provide material with excellent purity profiles (>99 GC area 96). Our final route provides significant improvements in terms of cost-efficiency, safety, scalability, and impurity content. Highlights of this strategy include two chemo-selective, Pd-catalyzed, deallylation reactions and an efficient reductive amination protocol. To circumvent the chemical instability of DCPA 1, an innovative isolation procedure was developed which reliably reduced the amount of Pd residue to less than 20 ppm. Following this protocol, impurities such as N-propylcyclopropyl-, mono-cyclopropyl-, and N-ethyl-cyclopropylamines (3, 4, and 17) were minimized to 0.06, not detectable, and 0.02%, respectively.