2-(N,N-diethylamino)benzylamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(N,N-diethylamino)benzylamine
• 英文别名: 2-(Aminomethyl)-N,N-diethylaniline
• 化学式: C₁₁H₁₈N₂
• 分子量: 178.277
• InChiKey: XCALVTLLSKYQMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-methyl3-(4-((amino(methylthio)methylene)carbamoyl)phenyl)-2-((tert-butoxycarbonyl)amino)propanoate 、 2-(N,N-diethylamino)benzylamine 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Discovery of acyl guanidine tryptophan hydroxylase-1 inhibitors

  摘要：

  An increasing number of diseases have been linked to a dysfunctional peripheral serotonin system. Given that tryptophan hydroxylase 1 (TPH1) is the rate limiting enzyme in the biosynthesis off serotonin, it represents an attractive target to regulate peripheral serotonin. Following up to our first disclosure, we report a new chemotype of TPH1 inhibitors where-by the more common central planar heterocycle has been replaced with an open-chain, acyl guanidine surrogate. Through our work, we found that compounds of this nature provide highly potent TPH1 inhibitors with favorable physicochemical properties that were effective in reducing murine intestinal 5-HT in vivo. Furthermore, we obtained a high resolution (1.90 angstrom) X-ray structure crystal structure of one of these inhibitors (compound 51) that elucidated the active conformation along with revealing a dimeric form of TPH1 for the first time. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.04.057
• 作为产物：
  描述：

  2-氟苯腈 、 二乙胺 在 dimethyl sulfide borane 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以70%的产率得到2-(N,N-diethylamino)benzylamine
  参考文献：
  名称：

  氨基硼氢化物。12.2-卤代苄腈与N，N-二烷基氨基硼氢化锂的新型串联S（N）Ar胺化-还原反应。

  摘要：

  已经开发了一种新颖的串联胺化还原反应，其中由2-卤代苄腈和N，N-二烷基氨基硼氢化锂（LAB）试剂生成2-（N，N-二烷基氨基）苄胺。据信这些反应是通过串联的S（N）Ar胺-还原机理发生的，其中LAB试剂通过N，N-二烷基氨基促进卤化物的取代，随后腈被还原。这种一锅法是现有合成方法的补充，并且是用较少的亲核胺对卤代苯进行亲核芳族取代的有吸引力的合成工具。该反应的（N，N-二烷基氨基）苄胺产物在简单的水性后处理步骤后容易分离，收率非常好至极佳。

  DOI：

  10.1021/jo001388j

文献信息

• [EN] COMPOUNDS AND COMPOSITIONS AS PDGFR KINASE INHIBITORS<br/>[FR] COMPOSÉS ET COMPOSITIONS POUVANT ÊTRE UTILISÉS EN TANT QU'INHIBITEURS DES KINASES PDGFR
  申请人：IRM LLC

  公开号：WO2013033620A1

  公开（公告）日：2013-03-07

  The invention provides compounds and pharmaceutical compositions thereof, which are useful as protein kinase inhibitors, as well as methods for using such compounds to treat, ameliorate or prevent a condition associated with abnormal or deregulated kinase activity. In some embodiments, the invention provides methods for using such compounds to treat, ameliorate or prevent diseases or disorders that involve abnormal activation of PDGFR (PDGFRα, PDGFRβ) kinases or c-kit and PDGFR (PDGFRα, PDGFRβ) kinases.

  这项发明提供了化合物及其药物组合物，这些化合物可用作蛋白激酶抑制剂，以及使用这些化合物来治疗、改善或预防与异常或失调激酶活性相关的疾病的方法。在某些实施方式中，该发明提供了使用这些化合物来治疗、改善或预防涉及PDGFR（PDGFRα、PDGFRβ）激酶或c-kit和PDGFR（PDGFRα、PDGFRβ）激酶异常激活的疾病或紊乱的方法。
• Aminoborohydrides. 12. Novel Tandem S_NAr Amination−Reduction Reactions of 2-Halobenzonitriles with Lithium <i>N,N</i>-Dialkylaminoborohydrides
  作者：Shannon Thomas、Christopher J. Collins、Jennifer R. Cuzens、David Spiciarich、Christian T. Goralski、Bakthan Singaram

  DOI：10.1021/jo001388j

  日期：2001.3.1

  A novel tandem amination-reduction reaction has been developed in which 2-(N,N-dialkylamino)benzylamines are generated from 2-halobenzonitriles and lithium N,N-dialkylaminoborohydride (LAB) reagents. These reactions are believed to occur through a tandem S(N)Ar amination-reduction mechanism wherein the LAB reagent promotes halide displacement by the N,N-dialkylamino group, and the nitrile is subsequently

  已经开发了一种新颖的串联胺化还原反应，其中由2-卤代苄腈和N，N-二烷基氨基硼氢化锂（LAB）试剂生成2-（N，N-二烷基氨基）苄胺。据信这些反应是通过串联的S（N）Ar胺-还原机理发生的，其中LAB试剂通过N，N-二烷基氨基促进卤化物的取代，随后腈被还原。这种一锅法是现有合成方法的补充，并且是用较少的亲核胺对卤代苯进行亲核芳族取代的有吸引力的合成工具。该反应的（N，N-二烷基氨基）苄胺产物在简单的水性后处理步骤后容易分离，收率非常好至极佳。
• Discovery of acyl guanidine tryptophan hydroxylase-1 inhibitors
  作者：Daniel R. Goldberg、Stéphane De Lombaert、Robert Aiello、Patricia Bourassa、Nicole Barucci、Qing Zhang、Vishwas Paralkar、Adam J. Stein、Jim Valentine、William Zavadoski

  DOI：10.1016/j.bmcl.2016.04.057

  日期：2016.6

  An increasing number of diseases have been linked to a dysfunctional peripheral serotonin system. Given that tryptophan hydroxylase 1 (TPH1) is the rate limiting enzyme in the biosynthesis off serotonin, it represents an attractive target to regulate peripheral serotonin. Following up to our first disclosure, we report a new chemotype of TPH1 inhibitors where-by the more common central planar heterocycle has been replaced with an open-chain, acyl guanidine surrogate. Through our work, we found that compounds of this nature provide highly potent TPH1 inhibitors with favorable physicochemical properties that were effective in reducing murine intestinal 5-HT in vivo. Furthermore, we obtained a high resolution (1.90 angstrom) X-ray structure crystal structure of one of these inhibitors (compound 51) that elucidated the active conformation along with revealing a dimeric form of TPH1 for the first time. (C) 2016 Elsevier Ltd. All rights reserved.