4-己酰基吡啶 | 23389-74-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-己酰基吡啶
• 英文名称: 4-hexanoylpyridine
• 英文别名: 1-pyridin-4-yl-hexan-1-one；1-(Pyridin-4-yl)hexan-1-one；1-pyridin-4-ylhexan-1-one
• CAS: 23389-74-4
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: ZVVOWSXOIPVAOB-UHFFFAOYSA-N

物化性质

• 沸点：
  309.18°C (rough estimate)
• 密度：
  1.0290 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  4-己酰基吡啶 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 4.5h， 以97%的产率得到α-pentyl-4-pyridinemethanol hydrochloride
  参考文献：
  名称：

  Controlling chemoselective transformations of 4-acylpyridines via a Pd–C catalytic hydrodechlorination–hydrogenation

  摘要：

  A novel Pd-C catalytic hydrodechlorination-hydrogenation was developed for a multi-step one-pot transformation of 4-acylpyridines. Under the selected conditions, 4-benzoylpyridines and 4-alkanoylpyridines were chemoselectively converted into the corresponding 4-benzylpiperidine hydrochlorides and alpha-alkyl-4-piperidinemethanol hydrochlorides, respectively. This catalytic method was performed simply by an addition of 1 equiv of CICH2CHCl2 to the conventional hydrogenation system and directly gave the crystalline piperidine hydrochlorides in practical quantitative yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.017
• 作为产物：
  描述：

  α-pentyl-4-pyridinemethanol 在 potassium permanganate 、 magnesium sulfate 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 生成 4-己酰基吡啶
  参考文献：
  名称：

  Comparative inhibition of tetrameric carbonyl reductase activity in pig heart cytosol by alkyl 4-pyridyl ketones

  摘要：

  Context and objective: The present study is to elucidate the comparative inhibition of tetrameric carbonyl reductase (TCBR) activity by alkyl 4-pyridyl ketones, and to characterize its substrate-binding domain.Materials and methods: The inhibitory effects of alkyl 4-pyridyl ketones on the stereoselective reduction of 4-benzoylpyridine (4-BP) catalyzed by TCBR were examined in the cytosolic fraction of pig heart.Results: Of alkyl 4-pyridyl ketones, 4-hexanoylpyridine, which has a straight-chain alkyl group of five carbon atoms, inhibited most potently TCBR activity and was a competitive inhibitor. Furthermore, cyclohexyl pentyl ketone, which is substituted by cyclohexyl group instead of phenyl group of hexanophenone, had much lower ability to be reduced than hexanophenone.Discussion and conclusion: These results suggest that in addition to a hydrophobic cleft corresponding to a straight-chain alkyl group of five carbon atoms, a hydrophobic pocket with affinity for an aromatic group is located in the substrate-binding domain of TCBR.

  DOI：

  10.3109/14756366.2013.790021

文献信息

• Steric effects ih the reaction of di(bromomagnesio)alkanes with carboxylic esters
  作者：Perséphone Canonne、Denis Bélanger、Gilles Lemay

  DOI：10.1016/s0040-4039(01)92402-5

  日期：1981.1

  Largely different product distributions were observed on the action of various carboxylic esters with 1,4-di(bromomagnesio)butane and its homologue 1,5-di(bromomagnesio)pentane. The much larger yields of reduction product with the latter are the evidence for the structural geometric requirements for the annelation step.

  在各种羧酸酯与1,4-二（溴镁）丁烷及其同系物1,5-二（溴镁）戊烷的作用下，观察到很大的产物分布。还原产物的产率要高得多，后者证明了去核步骤的结构几何要求。
• The Anion of 3-Methyl-2-pyridin-4-yl- 1,3-oxazine
  作者：Peter Sheldrake、Elizabeth Tyrrell、Shirin Mintias、Imran Shahid

  DOI：10.1081/scc-120021505

  日期：2003.1.7

  n-Butyllithium at -78degreesC readily abstracts the methine proton from the title compound. The anion reacts efficiently with a range of electrophiles to provide 4-pyridyl ketones upon acid hydrolysis.
• Hydroacylation of 1-Alkene with Heteroaromatic Aldehyde by Rh(I) and Additives
  作者：Chul-Ho Jun、Dae-Yon Lee、Jun-Bae Hong

  DOI：10.1016/s0040-4039(97)01562-1

  日期：1997.9

  Hydroacylation of 1-alkene with a heteroaromatic aldehyde such as pyridinecarboxaldehyde, thiophenecarboxaldehyde and furfural derivatives under cocatalyst of Wilkinson's complex and 2-amino-3-picoline gave poor yield of hydroacylated product. The addition of a catalytic amount of his(cyclopentadienyl)zirconium dichloride or bis(cyclopentadienyl)titanium dichloride as an additive dramatically increased the yield of the hydroacylated ketone product. (C) 1997 Elsevier Science Ltd.
• CANONNE, P.;BELANGER, D.;LEMAY, G., TETRAHEDRON LETT., 1981, 22, N 50, 4995-4998
  作者：CANONNE, P.、BELANGER, D.、LEMAY, G.

  DOI：——

  日期：——
• BESTIMMUNG VON KURZKETTIGER SRL-ALKOHOLDEHYDROGENASE (DHRS4) ALS BIOMARKER FÜR ENTZÜNDUNGEN UND INFEKTIONEN
  申请人：BRAHMS Aktiengesellschaft

  公开号：EP1856538A1

  公开（公告）日：2007-11-21