3-piperidinochromone | 40302-79-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-piperidinochromone
• 英文别名: 3-piperidino-4H-chromen-4-one；3-piperidin-1-ylchromen-4-one
• CAS: 40302-79-2
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: JKPBBAWTUKRUGO-UHFFFAOYSA-N

物化性质

• 熔点：
  137-138 °C
• 沸点：
  349.2±42.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-piperidinochromone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以90%的产率得到cis-3-piperidino-chroman-4-ol
  参考文献：
  名称：

  A NEW SYNTHESIS OF CIS-3-SUBSTITUTED CHROMAN-4-OLS

  摘要：

  3,3-Dibromochroman-4-ones on reaction with different heterocyclic secondary amines gave 3-substituted chromones. These on reduction with NaBH4 gave exclusively cis-3-heterocycle substituted chroman-4-ols in good yields.

  DOI：

  10.1081/scc-120005433
• 作为产物：
  描述：

  3-苯氧基丙酸 在 哌啶 、 乙醚 、 溴 、 phosphorus pentoxide 、 甲苯 作用下， 生成 3-piperidinochromone
  参考文献：
  名称：

  Colonge; Guyot, Bulletin de la Societe Chimique de France, 1958, p. 325,328

  摘要：

  DOI：

文献信息

• Syntheses and Evaluation of 2- or 3-(<i>N</i>-Cyclicamino)chromone Derivatives as Monoamine Oxidase Inhibitors
  作者：Koichi Takao、Tsukasa Sakatsume、Hitoshi Kamauchi、Yoshiaki Sugita

  DOI：10.1248/cpb.c20-00579

  日期：2020.11.1

  A series of 2-(N-cyclicamino)chromone derivatives (1a-4c) and 3-(N-cyclicamino)chromone derivatives (5a-8c) were synthesized, and their monoamine oxidase (MAO) A and B inhibitory activities were studied as part of a structure-activity relationship investigation. Compounds 1a-4c showed no remarkable inhibition for MAO-A or MAO-B, whereas compounds 5a-8c (with a few exceptions) showed significant and selective inhibition of MAO-B. Of these compounds, 7c,7-methoxy-3-(4-phenyl-1-piperazinyl)-4H-1-benzopyran-4-one inhibited MAO-B the most potently and selectively, having IC50 of 15 nM and an MAO-B selectivity index of more than 6700; c.f, 50 nM and 2000, respectively, for safinamide. The mode of inhibition of 7c to MAO-B was competitive and reversible. Considering the IC50 values and selectivity indices of the other synthetic compounds, the presence of the methoxy group on the chromone ring (R-2) of 7c seemed to increase MAO-B inhibition. Molecular docking analysis also supports this hypothesis. Our results suggest that 3-(N-cyclicamino)chromones are useful lead compounds for the development of MAO-B inhibitors.
• Substituted Chromones
  作者：Charles W. Winter、Cliff S. Hamilton

  DOI：10.1021/ja01136a008

  日期：1952.8
• Reaction of 3-Iodochromone with Nucleophiles 3. Formation of 2-Aminomethylene-3(2H)-benzofuranones by the Reaction with Secondary Amines
  作者：Yoshiaki Sugita、Takako Iwaki、Misaki Okamoto、Ichiro Yokoe

  DOI：10.3987/com-01-9169

  日期：——

  3-Iodochromone (4a) easily reacted with secondary amines in the presence of potassium carbonate to give 2-aminomethylene-3(2H)-benzofuranones in good yields. Under similar conditions without potassium carbonate, 4a was reacted with piperidine to give the enamino ketone (5) as the major product.
• The addition of amines to 3-bromochromone and 6-bromofurochromone. An unexpected ring contraction of the pyrone ring.
  作者：R.B. Gammill、S.A. Nash、S.A. Mizsak

  DOI：10.1016/s0040-4039(00)86006-2

  日期：1983.1
• GAMMILL, R. B.;NASH, S. A.;MIZSAK, S. A., TETRAHEDRON LETT., 1983, 24, N 33, 3435-3438
  作者：GAMMILL, R. B.、NASH, S. A.、MIZSAK, S. A.

  DOI：——

  日期：——