4-carbethoxy-1-ethyl-1,2,5,6-tetrahydropyridine | 162395-39-3

• 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
• 英文名称: 4-carbethoxy-1-ethyl-1,2,5,6-tetrahydropyridine
• 英文别名: ethyl 1-ethyl-3,6-dihydro-2H-pyridine-4-carboxylate
• CAS: 162395-39-3
• 化学式: C₁₀H₁₇NO₂
• 分子量: 183.25
• InChiKey: XNPPKXHLWQLMFB-UHFFFAOYSA-N

物化性质

• 沸点：
  249.2±35.0 °C(Predicted)
• 密度：
  1.015±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  4-carbethoxy-1-ethyl-1,2,5,6-tetrahydropyridine 在 盐酸 、 正丁基锂 、 氯化亚砜 、 氢气 作用下， 以 乙醚 、 水 、 甲苯 为溶剂， 反应 26.5h， 生成 4-[(4aR,5R,9bR)-2-ethyl-7-methyl-1,3,4,4a,5,9b-hexahydroindeno[1,2-c]pyridin-5-yl]benzoic acid
  参考文献：
  名称：

  Reversal of expected stereochemical outcome in the oppolzer reaction of a cyclic N-enoylsultam: Enantioselective synthesis and absolute configuration of antispermatogenic hexahydroindeno[1,2-c]pyridines

  摘要：

  p-Tolylmagnesium bromide added with high enantioselectivity to a cyclic enoylsultam (4), but the diastereofacial selectivity (determined by X-ray crystallography of the product) was opposite that reported for acyclic enoylsultams. The reaction was used in an enantioselective synthesis of antispermatogenic hexahydroindenopyridines and allowed the absolute configuration of the active enantiomer (1) to be determined. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00714-4
• 作为产物：
  描述：

  异烟酸乙酯 在 sodium tetrahydroborate 作用下， 生成 4-carbethoxy-1-ethyl-1,2,5,6-tetrahydropyridine
  参考文献：
  名称：

  β-氨基和β-铵基的分子内环化：1-氮杂双环的新合成途径

  摘要：

  用氢化三丁基锡处理1-（2-苯基硒乙基）-1，2，5，6-四氢吡啶（15）仅得到还原产物，表明5-己烯基9不愿进行闭环。如果通过在C4处引入酯基或通过其季铵盐来修饰自由基的性质，则很容易发生环化。尽管基团52给出了未被还原产物污染的1-甲基-1-氮杂双环[3.2.1。]辛基溴化物（55）的优异产率，但是21的双环产物伴随着一些还原的物质。后者中不需要的烯烃的产生可以通过使用季铵酯1-（2-溴乙基）-4-碳乙氧基-1-甲基-1,2,5,6-四氢吡啶鎓溴化物（35）消除。暴露于氢化三丁基锡，得到1：1个内酯/外酯混合物，分别是4-乙氧基-1-甲基-1-氮杂双环[3.2.1]辛基溴化物（37）。这些结果证明了当酯官能团与5-己烯基系统的双键连接时，酯官能团具有强大的极性效应，该性质可在自由基58的情况下得到利用。前体的处理，1-（2 -溴溴乙基）-3-碳乙氧基-1-甲基-3-吡咯啉溴化物（60）

  DOI：

  10.1021/jo000790v

文献信息

• Structure-Activity Studies of 2,3,4,4a,5,9b-Hexahydroindeno[1,2-c]pyridines as Antispermatogenic Agents for Male Contraception
  作者：C. Edgar Cook、Mansukh C. Wani、Joseph M. Jump、Yue-W. Lee、Patricia A. Fail、Stephanie A. Anderson、Yu-Q. Gu、Vladimir Petrow

  DOI：10.1021/jm00005a003

  日期：1995.3

  Analogs of (4aRS,5SR,9bRS)-2-ethyl-2,3,4,4a,5,9b-hexahydro-7-methyl-5-p-tolyl-1H-indeno[1,2-c]pyridine (Sandoz 20-438, 10a; R(1) = ethyl, R(2) = R(3) = methyl, R(4) = H) have been synthesized and tested in mice for their ability to reduce testes weight and disrupt spermatogenesis. The activity was strongly dependent on stereoisomerism and chirality, consistent with a mechanism of action involving interaction with a specific macromolecule. It was affected by changes in the nitrogen substituent and most strikingly by changes in the p-substituent of the 5-aryl ring. A hydrogen, fluorine, hydroxy, or methoxy substituent led to loss of activity, whereas methyl (Sandoz 20-438, 10a), carboxylate (RTI-4587-054, 10k; R(1) = ethyl, R(2) = methyl, R(3) = COOH, R(4) = H), ester (RTI-4587-056, 12b; R(1) = ethyl, R(2) = methyl, R(3) = COOMe, R(4) = H), formyl (RTI-4587-030, 12i; R(1) = ethyl, R2 = methyl, R(3) = CHO, R(4) = H), or hydroxymethyl (RTI-4587-055, 12g; R(1) = ethyl, R(2) = methyl, R(3) = CH2OH, R(4) = H) groups resulted in antispermatogenic compounds. Methyl ester 12b was an effective antifertility agent, without apparent effects on mating, when given orally to male mice at 7-15 mg/kg daily for 35 days. Further evaluation of these compounds as male contraceptive agents and probes for study of spermatogenesis appears warranted.
• Intramolecular Cyclization of β-Amino and β-Ammonio Radicals:  A New Synthetic Route to the 1-Azabicyclo[3.2.1]octyl- and -[2.2.1]heptyl Systems
  作者：Ernest W. Della、Paul A. Smith

  DOI：10.1021/jo000790v

  日期：2000.10.1

  with tributyltin hydride generates 58 which is found to cyclize with high regioselectivity, affording a convenient high-yielding synthesis of the endo/exo isomers of 3-carbethoxy-1-methyl-1-azoniabicyclo[2.2.1]heptyl bromide 57. The isomeric bicyclo[2.2.1]heptyl ester 63 was not detected. These observations are in accordance with predictions based upon frontier molecular orbital considerations.

  用氢化三丁基锡处理1-（2-苯基硒乙基）-1，2，5，6-四氢吡啶（15）仅得到还原产物，表明5-己烯基9不愿进行闭环。如果通过在C4处引入酯基或通过其季铵盐来修饰自由基的性质，则很容易发生环化。尽管基团52给出了未被还原产物污染的1-甲基-1-氮杂双环[3.2.1。]辛基溴化物（55）的优异产率，但是21的双环产物伴随着一些还原的物质。后者中不需要的烯烃的产生可以通过使用季铵酯1-（2-溴乙基）-4-碳乙氧基-1-甲基-1,2,5,6-四氢吡啶鎓溴化物（35）消除。暴露于氢化三丁基锡，得到1：1个内酯/外酯混合物，分别是4-乙氧基-1-甲基-1-氮杂双环[3.2.1]辛基溴化物（37）。这些结果证明了当酯官能团与5-己烯基系统的双键连接时，酯官能团具有强大的极性效应，该性质可在自由基58的情况下得到利用。前体的处理，1-（2 -溴溴乙基）-3-碳乙氧基-1-甲基-3-吡咯啉溴化物（60）
• Reversal of expected stereochemical outcome in the oppolzer reaction of a cyclic N-enoylsultam: Enantioselective synthesis and absolute configuration of antispermatogenic hexahydroindeno[1,2-c]pyridines
  作者：Joseph M. Jump、Andrew T. McPhail、C.Edgar Cook

  DOI：10.1016/s0040-4039(97)00714-4

  日期：1997.5

  p-Tolylmagnesium bromide added with high enantioselectivity to a cyclic enoylsultam (4), but the diastereofacial selectivity (determined by X-ray crystallography of the product) was opposite that reported for acyclic enoylsultams. The reaction was used in an enantioselective synthesis of antispermatogenic hexahydroindenopyridines and allowed the absolute configuration of the active enantiomer (1) to be determined. (C) 1997 Elsevier Science Ltd.