1-乙酰氧基-3-吡啶-4-基-丙烷 | 38456-25-6

• 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
• 中文名称: 1-乙酰氧基-3-吡啶-4-基-丙烷
• 英文名称: 3-(pyridin-4-yl)propyl acetate
• 英文别名: 3-(4-Pyridyl)propyl Acetate；3-pyridin-4-ylpropyl acetate
• CAS: 38456-25-6
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: GYPLDQSWQGHMKK-UHFFFAOYSA-N

物化性质

• 沸点：
  287.4±23.0 °C(Predicted)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-乙酰氧基-3-吡啶-4-基-丙烷 在 Rh/Al₂O₃ 盐酸 、 sodium hydroxide 、 4 A molecular sieve 、 氢气 、 sodium hydride 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 、 三正丁基叠氮化锡 、 二甲氨基甲酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 8.5h， 生成 cis-4-<4-(2H-tetrazol-5-yl)but-1-yl>piperidine-2-carboxylic acid
  参考文献：
  名称：

  4-(Tetrazolylalkyl)piperidine-2-carboxylic acids. Potent and selective N-methyl-D-aspartic acid receptor antagonists with a short duration of action

  摘要：

  We have prepared a series of cis-4-(tetrazolylalkyl)piperidine-2-carboxylic acids as potent and selective N-methyl-D-aspartic acid (NMDA) receptor antagonists. NMDA antagonists may prove to be useful therapeutic agents, for instance, as anticonvulsants, in the treatment of neurodegenerative disorders such as Alzheimer's disease and in the prevention of neuronal damage that occurs during cerebral ischemia. The compounds prepared were evaluated in vitro in both receptor binding assays ([H-3]CGS-19755, [H-3]AMPA, and [H-3]kainic acid) and in a cortical-wedge preparation (versus NMDA, quisqualic acid, and kainic acid) to determine affinity, potency, and selectivity. The new amino acids were also evaluated in vivo for their ability to block NMDA-induced convulsions in neonatal rats and NMDA-induced lethality in mice. The most potent compound of this series, 15 (LY233053), selectively displaced [H-3]CGS-19755 binding with an IC50 of 107 +/- 7 nM and selectively antagonized responses due to NMDA in a cortical-wedge preparation with an IC50 of 4.2 +/- 0.4-mu-M. Compound 15 blocked both NMDA-induced convulsions in neonatal rats (minimum effective dose (MED) = 20 mg/kg ip) and NMDA-induced lethality in mice (MED = 5 mg/kg ip). This is the first example of an NMDA receptor antagonist that incorporates a tetrazole moiety as an omega-acid bioisostere. These amino acid antagonists are also unique from their phosphonic acid counterparts in that they have a shorter duration of action in vivo. For the treatment of acute disorders such as stroke, where an NMDA antagonist would be administered parenterally, the shorter duration of action may be beneficial, e.g., allowing for better dosage control. The combination of potent NMDA receptor antagonism and a short duration of action may make these compounds useful therapeutic agents in the treatment of a variety of neurological disorders.

  DOI：

  10.1021/jm00105a016
• 作为产物：
  描述：

  4-吡啶丙醇 、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以73 %的产率得到1-乙酰氧基-3-吡啶-4-基-丙烷
  参考文献：
  名称：

  4-烷基吡啶的 C-磺酰化：通过亚烷基二氢吡啶中间体的形式甲基吡啶 C-H 活化

  摘要：

  在催化 DMAP 存在的情况下，用芳基磺酰氯和 Et 3 N处理后，4-甲基吡啶衍生物会转化为相应的芳基甲基吡啶砜。使用一系列芳基磺酰氯，各种烷基和芳基甲基吡啶的反应顺利进行。据信该反应涉及N-磺酰基 4-亚烷基二氢吡啶中间体，并导致未活化的甲基吡啶 C-H 键的形式磺酰化。

  DOI：

  10.1021/acs.joc.3c00017

文献信息

• Direct Methenylation of 4-Alkylpyridines Using Eschenmoser’s Salt
  作者：F. Christopher Pigge、Grant N. Shivers、Soe L. Tun、Shay L. McLean

  DOI：10.1055/a-1916-5335

  日期：2022.12

  4-Alkylpyridines are converted into conjugated 1,1-disubstituted alkenyl pyridines (vinyl pyridines) upon treatment with excess ethyl chloroformate, triethylamine, and Eschenmoser’s salt. The reaction proceeds under mild conditions via alkylidene dihydropyridine intermediates.

  在用过量的氯甲酸乙酯、三乙胺和 Eschenmoser 盐处理后，4-烷基吡啶转化为共轭的 1,1-二取代的烯基吡啶（乙烯基吡啶）。该反应在温和条件下通过亚烷基二氢吡啶中间体进行。
• Palladium-catalyzed allylation of 2- and 4-alkylpyridines via N-allyl alkylidene dihydropyridine intermediates
  作者：Grant N. Shivers、F. Christopher Pigge

  DOI：10.1016/j.tetlet.2023.154701

  日期：2023.9

  introduce allyl or cinnamyl groups to the picolyl positions of 2- or 4-alkylpyridines is described. Substituted N-allyl pyridinium salts are first treated with base (KOtBu) followed by catalytic [(η3-allyl)PdCl]2 and PPh3 to result in formal Pd-catalyzed transfer of N-allyl groups to the pyridine periphery. The reaction is believed to proceed through initial formation of nucleophilic alkylidene dihydropyridine

  描述了将烯丙基或肉桂基引入2-或4-烷基吡啶的吡啶甲基位置的方法。首先用碱(KO t Bu)处理取代的N-烯丙基吡啶鎓盐，然后用催化[(η 3 -烯丙基)PdCl] 2和PPh 3处理，以导致N-烯丙基正式Pd催化转移到吡啶外围。据信该反应通过最初形成亲核亚烷基二氢吡啶中间体进行，该中间体与(π-烯丙基)Pd(II)亲电子试剂反应，从而再生N-烯丙基吡啶鎓阳离子。然后通过将 Pd(0) 氧化加成到这些活化的烯丙基上来实现催化转化和吡啶产物的释放。
• ORNSTEIN, PAUL L.;SCHOEPP, DARRYLE D.;ARNOLD, M. BRIAN;LEANDER, J. DAVID;+, J. MED. CHEM., 34,(1991) N, C. 90-97
  作者：ORNSTEIN, PAUL L.、SCHOEPP, DARRYLE D.、ARNOLD, M. BRIAN、LEANDER, J. DAVID、+

  DOI：——

  日期：——