N-methoxycarbonyl-3-carboxymethyl-1,2,5,6-tetrahydropyridine | 76508-76-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: N-methoxycarbonyl-3-carboxymethyl-1,2,5,6-tetrahydropyridine
• 英文别名: dimethyl 3,6-dihydro-2H-pyridine-1,5-dicarboxylate
• CAS: 76508-76-4
• 化学式: C₉H₁₃NO₄
• 分子量: 199.207
• InChiKey: UQBXPWGIHMOGSU-UHFFFAOYSA-N

物化性质

• 沸点：
  279.6±40.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methoxycarbonyl-3-carboxymethyl-1,2,5,6-tetrahydropyridine 在 palladium diacetate 甲醇 、 氢氧化钾 、 dimethyl sulfide borane 、 sodium methylate 、 sodium hydride 、 magnesium 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 212.75h， 生成 帕罗西汀杂质04(单体)
  参考文献：
  名称：

  Efficient Heck Arylations of Cyclic and Acyclic Acrylate Derivatives Using Arenediazonium Tetrafluoroborates. A New Synthesis of the Antidepressant Drug (±)-Paroxetine

  摘要：

  The Heck arylation of acyclic- and cyclic-substituted acrylates using several arenediazonium tetrafluoroborates was investigated. Arylations were carried out under aerobic, ligand-free conditions to provide the corresponding substituted acrylates in moderate to high isolated yields. Heck arylations were usually completed in less than 2 h in refluxing methanol. The aza-endocyclic acrylate derivative 11a was converted into the antidepressant drug ((+)(-))-paroxetine in a concise new route in good overall yield.

  DOI：

  10.1021/ol060248e
• 作为产物：
  描述：

  3-[苄基-(2-甲氧基羰基乙基)-氨基]-丙酸乙酯 在 sodium tetrahydroborate 、 sodium hydride 、 碳酸氢钠 、 甲基磺酰氯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 29.0h， 生成 N-methoxycarbonyl-3-carboxymethyl-1,2,5,6-tetrahydropyridine
  参考文献：
  名称：

  Convenient Formal Synthesis of (±)‐Paroxetine

  摘要：

  A formal total synthesis of antidepressant (+/-)-paroxetine employing a solvent-free Heck reaction is disclosed.

  DOI：

  10.1080/00397910701545130

文献信息

• Potential GABA Uptake Inhibitors. Synthesis and Relative Stereochemistry of Some Aminopiperidinecarboxylic Acids.
  作者：Poul Jacobsen、Kjeld Schaumburg、Povl Krogsgaard-Larsen、Tamas Bartfai、Curt R. Enzell

  DOI：10.3891/acta.chem.scand.34b-0319

  日期：——
• Krogsgaard-Larsen; Jacobsen; Brehm, European Journal of Medicinal Chemistry, 1980, vol. 15, # 6, p. 529 - 535
  作者：Krogsgaard-Larsen、Jacobsen、Brehm、et al.

  DOI：——

  日期：——
• KROGSGAARD-LARSEN P.; JACOBSEN P.; BREHM L.; LARSEN J.-J.; SCHAUMBURG K., EUR. J. MED. CHEM.-CHIM. THER., 1980, 15, NO 6, 529-535
  作者：KROGSGAARD-LARSEN P.、 JACOBSEN P.、 BREHM L.、 LARSEN J.-J.、 SCHAUMBURG K.

  DOI：——

  日期：——
• Efficient Heck Arylations of Cyclic and Acyclic Acrylate Derivatives Using Arenediazonium Tetrafluoroborates. A New Synthesis of the Antidepressant Drug (±)-Paroxetine
  作者：Julio Cezar Pastre、Carlos Roque Duarte Correia

  DOI：10.1021/ol060248e

  日期：2006.4.1

  The Heck arylation of acyclic- and cyclic-substituted acrylates using several arenediazonium tetrafluoroborates was investigated. Arylations were carried out under aerobic, ligand-free conditions to provide the corresponding substituted acrylates in moderate to high isolated yields. Heck arylations were usually completed in less than 2 h in refluxing methanol. The aza-endocyclic acrylate derivative 11a was converted into the antidepressant drug ((+)(-))-paroxetine in a concise new route in good overall yield.
• Convenient Formal Synthesis of (±)‐Paroxetine
  作者：Subhash P. Chavan、Dushant A. Khobragade、Ashok B. Pathak、Uttam R. Kalkote

  DOI：10.1080/00397910701545130

  日期：2007.9.1

  A formal total synthesis of antidepressant (+/-)-paroxetine employing a solvent-free Heck reaction is disclosed.