(+/-)-3,4-dehydro-1,2-dimethyl-3-phenyl-4-ethoxycarbonyl-5-carboxypiperidine | 556826-70-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (+/-)-3,4-dehydro-1,2-dimethyl-3-phenyl-4-ethoxycarbonyl-5-carboxypiperidine
• 英文别名: diethyl 1,6-dimethyl-5-phenyl-3,6-dihydro-2H-pyridine-3,4-dicarboxylate
• CAS: 556826-70-1
• 化学式: C₁₉H₂₅NO₄
• 分子量: 331.412
• InChiKey: IMEOMAXRJGQOQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-3,4-dehydro-1,2-dimethyl-3-phenyl-4-ethoxycarbonyl-5-carboxypiperidine 在 正丁基锂 、 硫酸 、 potassium tert-butylate 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 ethyl 1,6-dimethyl-5β-hydroxy-5α-phenyl-3α-carboxypiperidine-4β-carboxylate
  参考文献：
  名称：

  Novel Secoergoline Derivatives Inhibit Both GABA and Glutamate Uptake in Rat Brain Homogenates:  Synthesis, in Vitro Pharmacology, and Modeling

  摘要：

  Three of twelve secoergoline derivatives (Z ethyl 4-[(ethoxycarbonylmethyl)methylamino]-2-methyl-3-phenylpent-2-enoate, 8; ethyl 1,6-dimethyl-3-oxo-5-phenyl-1,2,3,6-tetrahydropyridine-2-carboxylate, 9; Z methyl 4-[(methoxycarbonylmethyl)methylamino)-2-methyl-3-phenylpent-2-enoate, 11), containing bioisosteric sequences of GABA and Glu, inhibited both GABA and Glu transport through cerebrocortical membranes specifically. Compounds 8, 9, and 11 appeared to be equipotent inhibitors of GABA and Glu transport with IC50 values between 270 and 1100,muM, whereas derivatives 1-7, 10, and 12 were without effects. In the presence of GABA and Glu transport-specific nontransportable inhibitors, inhibition of GABA and Glu transport by 8, 9, and 11 proceeded in two phases. The two phases of inhibition were characterized by IC50 values between 4 and 180 nM and 360-1020 muM and different selectivity sequences. These findings may indicate the existence of some mechanism possibly mediated by a previously unrecognized GABA-Glu transporter. Derivatives with the cis, but not the trans configuration of bulky ester groups (8 vs 7 and 11 vs 12) showed significant inhibitory effect (IC50 values of 270,muM vs >>1000 muM and 1100 muM vs >>1000 muM on GABA transport, respectively). The cis-trans selectivity can be explained by docking these secoergolines in a three-dimensional model of the second and third transmembrane helices of GABA transporter type 1.

  DOI：

  10.1021/jm040809c
• 作为产物：
  描述：

  diethyl 5β-hydroxy-1,6-dimethyl-5α-phenyl-piperidine-3α,4β-dicarboxylate 在 硫酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以50%的产率得到(+/-)-3,4-dehydro-1,2-dimethyl-3-phenyl-4-ethoxycarbonyl-5-carboxypiperidine
  参考文献：
  名称：

  具有基本功能的吲哚化学。第七部分。斯托贝反应的新观点

  摘要：

  在进行琥珀酸二酯衍生物 (1) 的 Stobbe 反应时，发现不同的路线会导致不同的吲哚衍生物 (2-5)，这取决于所应用的反应条件，从而扩大了该有用程序的范围和限制。更简单的吡咯烷 (13) 和哌啶衍生物 (14, 15) 也通过应用分子内 Stobbe 反应获得。

  DOI：

  10.3987/com-02-9628