(2-氯-4-吡啶)-二甲胺 | 59047-70-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (2-氯-4-吡啶)-二甲胺
• 英文名称: 2-chloro-4-(dimethylamino)pyridine
• 英文别名: 2-chloro-4-pyridyl(dimethyl)amine；2-chloro-N,N-dimethylpyridin-4-amine
• CAS: 59047-70-0
• 化学式: C₇H₉ClN₂
• 分子量: 156.615
• InChiKey: HQNSWBRZIOYGAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  (2-氯-4-吡啶)-二甲胺 在 potassium phosphate 、 copper(l) iodide 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 N-[(1R,2R)-2-[[4-(dimethylamino)pyridin-2-yl]amino]cyclohexyl]-2,4,6-trimethyl-3-nitrobenzenesulfonamide
  参考文献：
  名称：

  Cu-Catalyzed Selective Mono-N-pyridylation: Direct Access to 2-AminoDMAP/Sulfonamides as Bifunctional Organocatalysts

  摘要：

  Direct and selective mono-N-pyridylation of trans-(R,R)-cyclohexane-1,2-diamine is described here. Facile preparation of a novel chiral 2-aminoDMAP core catalaphore via Cu catalysis has led to the development of various sulfonamide/2-aminoDMAPs as bifunctional acid/base organocatalysts (most in two steps overall), which have been shown to very effectively promote asymmetric conjugate addition of acetylacetone to trans-beta-nitroolefins with good to excellent yields (87-93%) and enantioselectivites (up to 99%).

  DOI：

  10.1021/jo302713b
• 作为产物：
  描述：

  2,4,6-三氯吡啶 在 正丁基锂 、 四丁基氟化铵 、 一水合肼 、 copper(II) sulfate 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 48.5h， 生成 (2-氯-4-吡啶)-二甲胺
  参考文献：
  名称：

  Regiochemically Flexible Substitutions of Di-, Tri-, and Tetrahalopyridines:  The Trialkylsilyl Trick

  摘要：

  2,4-Difluoropyridine, 2,4-dichloropyridine, 2,4,6-trifluoropyridine, 2,4,6-trichloropyridine and 2,3,4,6-tetrafluoropyridine react with standard nucleophiles exclusively at the 4-position under halogen displacement. However, the regioselectivity can be completely reversed if a trialkylsilyl group is introduced in the 5-position of the 2,4-dihalopyridines or in the 3-position of the 2,4,6-trihalopyridines or 2,3,4,6-tetrahalopyridine. Then only the halogen most remote from the bulky silyl unit (at the 2-position in the case of the 2,4-halopyridines, at the 6-position with the other substrates) gets involved in the exchange process. After removal of the silyl protective group the nucleophile is invariably found to occupy the nitrogen-neighboring position.

  DOI：

  10.1021/jo047962z

文献信息

• [EN] PYRAZOLOPYRIMIDIN-2-YL DERIVATIVES AS JAK INHIBITORS<br/>[FR] DÉRIVÉS DE PYRAZOLOPYRIMIDIN-2-YLE UTILISÉS COMME INHIBITEURS DE JAK
  申请人：ALMIRALL SA

  公开号：WO2015086693A1

  公开（公告）日：2015-06-18

  New pyrazolopyridmiin-2-yl derivatives are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of Janus Kinases (JAK).

  新的吡唑吡啶-2-基衍生物被披露；以及它们的制备方法，包含它们的药物组合物以及它们作为Janus激酶（JAK）抑制剂在治疗中的用途。
• [EN] FUSED HETEROCYCLIC COMPOUNDS AS OREXIN RECEPTOR MODULATORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES CONDENSÉS EN TANT QUE MODULATEURS DE RÉCEPTEUR D'OREXINE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2011050200A1

  公开（公告）日：2011-04-28

  Disubstituted 3,8-diaza-bicyclo[4.2.0]octane and 3,6-diazabicyclo [3.2.0]heptane compounds are described, which are useful as orexin receptor modulators. Such compounds may be useful in pharmaceutical compositions and methods for the treatment of diseased states, disorders, and conditions mediated by orexin activity, such as insomnia.

  描述了二取代的3,8-二氮杂双环[4.2.0]辛烷和3,6-二氮杂双环[3.2.0]庚烷化合物，这些化合物可用作促进睡眠素受体的调节剂。这些化合物可能在药物组合物和治疗由促进睡眠素活性介导的疾病状态、紊乱和症状的方法中有用，比如失眠。
• [EN] DIARYLAMINE-SUBSTITUTED QUINOLONES USEFUL AS INDUCIBLE NITRIC OXIDE SYNTHASE INHIBITORS<br/>[FR] QUINOLONES SUBSTITUÉES PAR DIARYLAMINE UTILES COMME INHIBITEURS DE L'OXYDE NITRIQUE SYNTHASE INDUCTIBLE.
  申请人：KALYPSYS INC

  公开号：WO2009029617A1

  公开（公告）日：2009-03-05

  Novel diarylamine-substituted quinolone compounds and pharmaceutical compositions, certain of which have been found to inhibit inducible NOS synthase have been discovered, together with methods of synthesizing and using the compounds including methods for the treatment of iNOS-mediated diseases in a patient by administering the compounds.

  已发现新的含有二芳胺基取代喹诺酮化合物和药物组合物，其中一些已被发现能抑制诱导型NOS合成酶，还包括合成和使用这些化合物的方法，包括通过给患者施用这些化合物治疗iNOS介导的疾病的方法。
• First Direct C-2-Lithiation of 4-DMAP. Convenient Access to Reactive Functional Derivatives and Ligands
  作者：David Cuperly、Philippe Gros、Yves Fort

  DOI：10.1021/jo016064p

  日期：2002.1.1

  The first direct alpha-lithiation of 4-DMAP has been performed via reaction with the BuLi-Me(2)N(CH(2))(2)OLi (BuLi-LiDMAE) reagent. This new methodology avoids the use of a activation-lithiation-regeneration sequence or halogen-metal exchange classically employed. New useful DMAP-containing synthons and polyheterocycles have been efficiently prepared.

  通过与BuLi-Me（2）N（CH（2））（2）OLi（BuLi-LiDMAE）试剂反应，完成了4-DMAP的第一个直接α-锂化反应。这种新方法避免了传统上使用的活化-锂化-再生序列或卤素金属交换。已经有效地制备了新的有用的含DMAP的合成子和多杂环。
• Enantioselective Organocatalytic Direct Michael Addition of Nitroalkanes to Nitroalkenes Promoted by a Unique Bifunctional DMAP-Thiourea
  作者：Constantinos Rabalakos、William D. Wulff

  DOI：10.1021/ja805390k

  日期：2008.10.15

  synthesized, and evaluated for the asymmetric Michael addition of nitroalkanes to nitroalkenes. The obdurate nature of this reaction has made this a formidable challenge to subdue by asymmetric catalysis. The catalyst design includes a thiourea function to activate the nitroalkene by a double H-bond and a 4-dimethylaminopyridine unit to deprotonate the nitroalkane and to bind the resulting nitronate anion also

  设计、合成并评估了一种用于硝基烷烃与硝基烯烃的不对称迈克尔加成反应的新催化剂。这种反应的顽固性质使其成为通过不对称催化克服的艰巨挑战。催化剂设计包括硫脲功能，通过双 H 键和 4-二甲氨基吡啶单元激活硝基烯烃，使硝基烷烃去质子化，并通过双 H 键结合所得硝基阴离子。催化剂的手性支架是 2,2'-diamino-1,1'-binaphthalene (BINAM)，通过硫脲单元和二甲氨基吡啶部分 (DMAP) 通过两个氨基连接制备双共轭物. 所得催化剂将影响硝基烷烃与各种硝基苯乙烯的反应，并在 10 种底物范围内提供出色的不对称诱导 (91-95% ee)。值得注意的是，不对称诱导随着催化剂负载量的降低而增加，在 2 mol% 的负载下速率和诱导之间的最佳折衷。