(2-chloropyridin-3-yl)-cyclohexylmethyl-amine | 906371-81-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (2-chloropyridin-3-yl)-cyclohexylmethyl-amine
• 英文别名: 2-chloro-N-(cyclohexylmethyl)pyridin-3-amine
• CAS: 906371-81-1
• 化学式: C₁₂H₁₇ClN₂
• 分子量: 224.733
• InChiKey: ITLOBICNHRRSBM-UHFFFAOYSA-N

物化性质

• 沸点：
  360.2±22.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-chloropyridin-3-yl)-cyclohexylmethyl-amine 在 palladium diacetate 、 1,4-双(二苯基膦)丁烷 水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 醋酸异丙酯 、 异丙醇 为溶剂， 反应 25.17h， 生成 1-(Cyclohexylmethyl)-1,3-dihydro-2H-imidazo<4,5-b>pyridin-2-one
  参考文献：
  名称：

  Efficient Access to Cyclic Ureas via Pd-Catalyzed Cyclization

  摘要：

  An efficient regioselective method for the preparation of structurally diverse imidazopyridinones and benzoimidazolones starting from readily available and economical starting materials is described. High-yielding reductive alkylation of electron-deficient o-haloarylamines followed by treatment with inexpensive N-chlorosulfonyl isocyanate afforded primary ureas in good overall yields. A Pd-catalyzed urea cyclization reaction furnished imidazopyridinones and benzoimidazolones in excellent yields. Overall, the developed chemistry provides rapid access to pharmaceutically important heterocyclic compounds with high efficiency.

  DOI：

  10.1021/ol061233j
• 作为产物：
  描述：

  3-氨基-2-氯吡啶 在 sodium tris(acetoxy)borohydride 、 三氟乙酸 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 生成 (2-chloropyridin-3-yl)-cyclohexylmethyl-amine
  参考文献：
  名称：

  钯催化2-氯-3-氨基杂环酰胺化反应合成咪唑并[4,5- b ]吡啶和咪唑并[4,5- b ]吡嗪

  摘要：

  使用Pd催化的酰胺偶联反应描述了咪唑并[4,5- b ]吡啶和-吡嗪的简便合成方法。通过该反应，可以快速获得在N1和C2处被取代的产物。已经证明了与天然产物戊糖苷有关的模型系统，以及诱变剂1-Me-5-PhIP的全合成。

  DOI：

  10.1021/ol300359s

文献信息

• Efficient Access to Azaindoles and Indoles
  作者：Mark McLaughlin、Michael Palucki、Ian W. Davies

  DOI：10.1021/ol061232r

  日期：2006.7.1

  An expedient, catalytic method for the synthesis of diverse azaindoles and indoles, starting from readily available and inexpensive starting materials, is described. Conditions were developed for effective reductive alkylation of electron-deficient o-chloroarylamines, substrates previously viewed as poor partners in this reaction. The derived N-alkylated o-chloroarylamines were elaborated to N-alkylazaindoles and N-alkylindoles via a novel one-pot process comprising copper-free Sonogashira alkynylation and a base-mediated indolization reaction.
• An Improved Synthesis of Imidazo[4,5-<i>b</i>]pyridines and Imidazo[4,5-<i>b</i>]pyrazines by Palladium Catalyzed Amidation using Xantphos in a 1,4-Dioxane:<i>tert</i>-Amyl Alcohol Solvent System
  作者：Adam J. Rosenberg、Ijaz Ahmed、Robert J. Wilson、Theresa M. Williams、Lauren Kaminsky、Daniel A. Clark

  DOI：10.1002/adsc.201400465

  日期：2014.11.3

  AbstractHerein an improved protocol for the synthesis of imidazo[4,5‐b]pyridines and imidazo[4,5‐b]pyrazines using a palladium‐catalyzed amidation that utilizes Xantphos as an ancillary phosphine ligand is reported. The use of a binary solvent system comprised of 1,4‐dioxane and tert‐amyl alcohol was crucial in eliminating unwanted by‐products.magnified image
• Efficient Access to Cyclic Ureas via Pd-Catalyzed Cyclization
  作者：Mark McLaughlin、Michael Palucki、Ian W. Davies

  DOI：10.1021/ol061233j

  日期：2006.7.1

  An efficient regioselective method for the preparation of structurally diverse imidazopyridinones and benzoimidazolones starting from readily available and economical starting materials is described. High-yielding reductive alkylation of electron-deficient o-haloarylamines followed by treatment with inexpensive N-chlorosulfonyl isocyanate afforded primary ureas in good overall yields. A Pd-catalyzed urea cyclization reaction furnished imidazopyridinones and benzoimidazolones in excellent yields. Overall, the developed chemistry provides rapid access to pharmaceutically important heterocyclic compounds with high efficiency.
• Synthesis of Imidazo[4,5-<i>b</i>]pyridines and Imidazo[4,5-<i>b</i>]pyrazines by Palladium Catalyzed Amidation of 2-Chloro-3-amino-heterocycles
  作者：Adam J. Rosenberg、Jinbo Zhao、Daniel A. Clark

  DOI：10.1021/ol300359s

  日期：2012.4.6

  A facile synthesis of imidazo[4,5-b]pyridines and -pyrazines is described using a Pd-catalyzed amide coupling reaction. This reaction provides quick access to products with substitution at N1 and C2. A model system relevant to the natural product pentosidine has been demonstrated, as well as the total synthesis of the mutagen 1-Me-5-PhIP.

  使用Pd催化的酰胺偶联反应描述了咪唑并[4,5- b ]吡啶和-吡嗪的简便合成方法。通过该反应，可以快速获得在N1和C2处被取代的产物。已经证明了与天然产物戊糖苷有关的模型系统，以及诱变剂1-Me-5-PhIP的全合成。