2,6-dipropynylpyridine

• 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: 2,6-dipropynylpyridine
• 英文别名: 3,5-Bis(prop-1-ynyl)pyridine
• 化学式: C₁₁H₉N
• 分子量: 155.199
• InChiKey: PIOWRYSSYZMZHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,6-dipropynylpyridine 在 tris[N-(tert-butyl)(3,5-dimethylphenyl)amido]molybdenum(VI) propylidyne 、 tris(2-hydroxy-3-isopropylbenzyl)methane 作用下， 以 四氯化碳 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  高度活跃的多配体基炔烃复分解催化剂

  摘要：

  已开发出由钼（VI）丙炔和多齿三（2-羟基苄基）甲烷配体组成的炔烃复分解催化剂，具有出色的稳定性（在室温下在溶液中可保持活性数月），高活性和宽泛的官能团耐受性。单丙炔基或二丙炔基底物（包括具有挑战性的杂环底物（例如吡啶））的均二聚和环寡聚在封闭系统中于40–55°C下有效进行。已经研究了配体的结构和催化活性的关系，这表明多齿酚配体的邻位对这种催化剂体系的稳定性和活性至关重要。

  DOI：

  10.1002/chem.201505174
• 作为产物：
  描述：

  3,5-二溴吡啶 、 丙炔 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 N-甲基吡咯烷酮 为溶剂， 160.0 ℃ 、200.0 kPa 条件下， 反应 0.17h， 以89%的产率得到3-溴-5-(1-丙炔)吡啶
  参考文献：
  名称：

  Development of a Continuous-Flow Sonogashira Cross-Coupling Protocol using Propyne Gas under Process Intensified Conditions

  摘要：

  The development of a continuous-flow Sonogashira cross-coupling protocol using propyne gas for the synthesis of a key intermediate in the manufacturing of a beta-amyloid precursor protein cleaving enzyme 1 (BACE1) inhibitor, currently undergoing late stage clinical trials for a disease-modifying therapy of Alzheimer's disease, is described. Instead of the currently used batch manufacturing process for this intermediate that utilizes TMS-propyne as reagent, we herein demonstrate the safe utilization of propyne gas, as a cheaper and more atom efficient reagent, using an intensified continuous-flow protocol under homogeneous conditions. The flow process afforded the target intermediate with a desired product selectivity of similar to 91% (vs the bis adduct) after a residence time of 10 min at 160 degrees C. The continuous-flow process compares favorably with the batch process, which uses TMS-propyne and requires overnight processing, TBAF as an additive, and a significantly higher loading of Cu co catalyst.

  DOI：

  10.1021/acs.oprd.7b00160

文献信息

• Tryptase inhibitors
  申请人：——

  公开号：US20040067943A1

  公开（公告）日：2004-04-08

  Compounds of the formula (I), in which M is a central building block selected from the group below in which Al, A2, K1 and K2 are as defined in the description, are novel effective tryptase inhibitors.

  式(I)的化合物，其中M是从以下组中选择的中心构建块，其中Al，A2，K1和K2如描述中所定义，是新颖有效的胰蛋白酶抑制剂。
• TRYPTASE INHIBITORS
  申请人：Altana Pharma AG

  公开号：EP1368317B1

  公开（公告）日：2006-12-27
• US7060716B2
  申请人：——

  公开号：US7060716B2

  公开（公告）日：2006-06-13
• [EN] TRYPTASE INHIBITORS<br/>[FR] INHIBITEURS DE TRYPTASE
  申请人：BYK GULDEN LOMBERG CHEM FAB

  公开号：WO2002066430A1

  公开（公告）日：2002-08-29

  Compounds of the formula (I), in which M is a central building block selected from the group below in which A1, A2, K1 and K2 are as defined in the description, are novel effective tryptase inhibitors.
• Highly Active Multidentate Ligand‐Based Alkyne Metathesis Catalysts
  作者：Ya Du、Haishen Yang、Chengpu Zhu、Michael Ortiz、Kenji D. Okochi、Richard Shoemaker、Yinghua Jin、Wei Zhang

  DOI：10.1002/chem.201505174

  日期：2016.6

  Alkyne metathesis catalysts composed of molybdenum(VI) propylidyne and multidentate tris(2‐hydroxylbenzyl)methane ligands have been developed, which exhibit excellent stability (remains active in solution for months at room temperature), high activity, and broad functional‐group tolerance. The homodimerization and cyclooligomerization of monopropynyl or dipropynyl substrates, including challenging

  已开发出由钼（VI）丙炔和多齿三（2-羟基苄基）甲烷配体组成的炔烃复分解催化剂，具有出色的稳定性（在室温下在溶液中可保持活性数月），高活性和宽泛的官能团耐受性。单丙炔基或二丙炔基底物（包括具有挑战性的杂环底物（例如吡啶））的均二聚和环寡聚在封闭系统中于40–55°C下有效进行。已经研究了配体的结构和催化活性的关系，这表明多齿酚配体的邻位对这种催化剂体系的稳定性和活性至关重要。