4-chloro-2-pentanoylpyridine | 896139-38-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-chloro-2-pentanoylpyridine
• 英文别名: 1-(4-chloropyridin-2-yl)pentan-1-one；1-(4-Chloro-2-pyridinyl)-1-pentanone
• CAS: 896139-38-1
• 化学式: C₁₀H₁₂ClNO
• 分子量: 197.664
• InChiKey: OGRCIMXLAURFQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  286.9±25.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-2-pentanoylpyridine 在 Saccharomyces cerevisiae 、 18-冠醚-6 、 葡萄糖 、 potassium hydride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 80.0h， 生成 (S)-(-)-4-(N,N-dimethylamino)-2-[(1-methoxypentyl)pyridine]
  参考文献：
  名称：

  Biocatalytic preparation of optically active 4-(N,N-dimethylamino)pyridines for application in chemical asymmetric catalysis

  摘要：

  4-Chloro-2-(1-hydroxybenzyl)pyridine and 4-chloro-2-(1-hydroxyalkyl)pyridines were obtained with moderate to excellent enantiomeric excesses and high isolated yields by bioreduction with Baker's yeast of the corresponding ketones. The resulting optically active alcohols were transformed into adequate DMAP derivatives, which have been applied in asymmetric catalytic processes as nucleophilic catalysts in the stereoselective chemical alkoxycarbonylation of 1-phenylethanol or as chiral ligands in the enantioselective addition of diethylzinc to benzaldehyde. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.03.018
• 作为产物：
  描述：

  4-氯吡啶 N-氧化物 在 二甲氨基甲酰氯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 220.0h， 生成 4-chloro-2-pentanoylpyridine
  参考文献：
  名称：

  Chemoenzymatic synthesis of chiral 4-(N,N-dimethylamino)pyridine derivatives

  摘要：

  Chiral 4-(N,N-dimethylamino)pyridine derivatives have been prepared through a chemoenzymatic synthesis where the enzymatic kinetic resolution of a family of 4-chloro-2-(1-hydroxyalkyl)pyridines is the key step for the formation of potentially important chiral catalysts. Pseudomonas cepacia lipase (PSL) showed excellent enantioselectivity in the acylation of the (R)-enantiomers (E > 200) using vinyl acetate as acylating agent and THF as solvent, obtaining products and substrates enantiomerically pure and with excellent yields. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2005.09.006

文献信息

• Biocatalytic Transamination for the Asymmetric Synthesis of Pyridylalkylamines. Structural and Activity Features in the Reactivity of Transaminases
  作者：María López-Iglesias、Daniel González-Martínez、Vicente Gotor、Eduardo Busto、Wolfgang Kroutil、Vicente Gotor-Fernández

  DOI：10.1021/acscatal.6b00686

  日期：2016.6.3

  set of transaminases has been investigated for the biocatalytic amination of 1-(4-chloropyridin-2-yl)alkan-1-ones. The influence of the chain length of the n-1-alkanone at the C-2 position of the pyridine has been studied in the reaction with different (R)- and (S)-selective transaminases. Thus, enantiopure amines were isolated with high purity starting from a wide selection of prochiral ketones. On the

  已经研究了一组转氨酶对1-（4-氯吡啶-2-基）烷-1-1-酮的生物催化胺化。在与不同的（R）-和（S）-选择性转氨酶反应中，已经研究了吡啶-1-碳链上正-1-烷酮的链长的影响。因此，从多种前手性酮开始，以高纯度分离出对映纯胺。在一方面，优异的产率（从97至> 99％的转化率，高达93％的分离产率）和立体选择性的值（> 99％ee的两个对映体的胺）被发现为Ñ-1-链烷酮线性短链取代基，如乙酮或丙酮。另一方面，只有当使用进化的酶，例如（R）-节杆菌的进化变体时，才可以接受更多受阻的底物。（ArRmut11-TA）。最初的常见结构特征是在吡啶核的C-4位上存在氯原子，该氯原子可提高起始酮的反应性，从而为引入其他化学官能团提供了额外的通用性，使其更加复杂和适用有机分子。为了更深入地了解不同转氨酶的底物特异性，通过改变吡啶环上乙酰基的位置以及使用相关的苯乙酮衍生物，可以考虑其他结构特征。
• Photoinduced Divergent Alkylation/Acylation of Pyridine <i>N</i>-Oxides with Alkynes under Anaerobic and Aerobic Conditions
  作者：Jin-hui Xu、Wen-bin Wu、Jie Wu

  DOI：10.1021/acs.orglett.9b01940

  日期：2019.7.5

  Ortho-alkylated and ortho-acylated pyridines have been conveniently synthesized from pyridine N-oxides and alkynes under visible-light-mediation in a metal-free manner. The alkynes served as both alkylating and acylating agents via switching between anaerobic and aerobic conditions. The overall strategy accommodates a broad scope of substituted pyridine N-oxides and alkynes, with excellent regioselectivity

  已经在可见光-介导下以无金属的方式方便地由吡啶N-氧化物和炔烃合成了邻烷基化和邻酰基化的吡啶。炔通过在厌氧和需氧条件之间切换而同时充当烷基化剂和酰化剂。总体策略适用于广泛范围的取代吡啶N-氧化物和炔烃，在许多情况下具有出色的区域选择性。