1-methyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid ethyl ester | 106810-65-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-methyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid ethyl ester
• 英文别名: ethyl 1-methyl-1,2,3,4-tetrahydroquinoline-2-carboxylate；ethyl 1-methyl-3,4-dihydro-2H-quinoline-2-carboxylate
• CAS: 106810-65-5
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: LEHOBOBILRSUGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  328.5±35.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  1-methyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid ethyl ester 在 氨 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 1-甲基-1,2,3,4-四氢喹啉-2-甲酰胺
  参考文献：
  名称：

  ANTAGONISTS OF THE TRPV1 RECEPTOR AND USES THEREOF

  摘要：

  本申请涉及的化合物是TRPV1拮抗剂，其化学式为（I），其中变量Ar1，L1，R1，R2，R3，R4，R5，Y1，Y2和Y3如描述中所定义，对于治疗由辣椒素受体活性引起或加剧的疾病是有用的。

  公开号：

  US20080153871A1
• 作为产物：
  描述：

  1,2,3,4-四氢喹啉-2-羧酸乙酯 生成 1-methyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• A new synthesis of cyclic α-amino acid derivatives by the intramolecular reaction of magnesium carbenoid with N-magnesio arylamine as the key reaction
  作者：Tohru Ohbayashi、Shintaro Mitsunaga、Tsuyoshi Satoh

  DOI：10.1016/j.tetlet.2007.09.003

  日期：2007.10

  A new synthesis of pipecolic acid and homopipecolic acid derivative was accomplished from 1-chloroalkyl p-tolyl sulfoxides having a 2-aminophenyl group at the ω-position by treatment with i-PrMgCl via the intramolecular reaction of magnesium carbenoid with N-magnesio arylamine. In a similar way, proline and pipecolic acid derivatives were synthesized from 1-chloroalkyl p-tolyl sulfoxides having an

  通过在i- PrMgCl的作用下，通过羧甲基镁与N-镁芳基胺的分子内反应，由ω-位具有2-氨基苯基的1-氯烷基对甲苯基亚砜完成了新的胡椒酸和高哌酸衍生物的合成。以类似的方式，由在ω-位具有芳基氨基的1-氯烷基对甲苯基亚砜合成脯氨酸和胡椒酸衍生物。
• Asymmetric synthesis of cyclic α-amino acid derivatives by the intramolecular reaction of magnesium carbenoid with an N-magnesio arylamine
  作者：Shintaro Mitsunaga、Tohru Ohbayashi、Shimpei Sugiyama、Takahito Saitou、Makoto Tadokoro、Tsuyoshi Satoh

  DOI：10.1016/j.tetasy.2009.06.024

  日期：2009.7

  The synthesis of pipecolic acid and homopipecolic acid derivatives was developed from ω-(2-aminophenyl)-1-chloroalkyl p-tolyl sulfoxides by treatment with i-PrMgCl. An intramolecular nucleophilic substitution reaction of a magnesium carbenoid with an N-magnesio arylamine is the key step of this reaction. Proline and pipecolic acid derivatives were also synthesized from ω-(arylamino)-1-chloroalkyl p-tolyl

  通过用i- PrMgCl处理，从ω-（2-氨基苯基）-1-氯烷基对甲苯基亚砜开发了胡椒酸和高哌酸衍生物的合成方法。羧甲基镁与N-镁芳基胺的分子内亲核取代反应是该反应的关键步骤。脯氨酸和胡椒酸衍生物也由ω-（芳基氨基）-1-氯烷基对甲苯基亚砜通过相同的化学方法合成。从对映体纯的（1 S，R S）-1-氯-3- [2-（N-甲基氨基）苯基]丙基对甲苯基亚砜开始，对映体纯的（R获得了）-哌酸衍生物。事实证明，类胡萝卜素镁与N-镁芳基胺的分子内亲核取代反应是通过类胡萝卜素碳的转化而发生的。还讨论了这些反应的立体化学。
• Chemoenzymatic Enantioselective Synthesis of the Hancock Alkaloids (S)- and (R)-Galipeine, (S)-Cuspareine, (S)-Galipinine, and (S)-Angustureine
  作者：Gaspar Diaz-Muñoz、Nilton Gonçalves da Cruz、Amanda Silva de Miranda、Henriete da Silva Vieira、Markus Kohlhoff、João Guilherme Pereira Mendonça、Marisa Alves Nogueira Diaz

  DOI：10.1055/a-1984-9689

  日期：2023.4

  The enantioselective synthesis of the Hancock 1,2,3,4-tetrahydroquinoline alkaloids (S)-galipeine, (S)-cuspareine, (S)-galipinine, and (S)-angustureine and the nonnatural enantiomer (R)-galipeine is described herein. The target compounds were obtained in five steps from a racemic quinaldinic acid derived α-amino ester in overall yields of 21.2% to 37.5%. The synthetic route comprised two key steps:

  Hancock 1,2,3,4-四氢喹啉生物碱 ( S )-galipeine、( S )-cuspareine、( S )-galipinine 和 ( S )-angustureine 以及非天然对映异构体 ( R )-galipeine 的对映选择性合成是此处描述。目标化合物由外消旋喹啉甲酸衍生的α-氨基酯经五步制得，总收率为21.2%～37.5%。合成路线包括两个关键步骤：控制 C-2 立体中心的酶促动力学拆分，提供 ( R )- 和 ( S )-α-氨基酯作为关键手性中间体，分别具有 94% 和 72% ee，以及 Wittig ( R )- 和 (S )-α-氨基醛合成子与相应的鏻盐使用相转移系统 ( t -BuOH/CH 2 Cl 2 )，从而允许在 C-2 处引入烷基取代基。最后，对映选择性合成结束于 Wittig 加合物上烯烃键的催化氢化，以提供目标 Hancock 生物碱，包括
• Antagonists of the TRPV1 receptor and uses thereof
  申请人：Abbott Laboratories

  公开号：EP2450346A1

  公开（公告）日：2012-05-09

  The present application is directed to compounds that are TRPV1 antagonists and have formula(I): wherein variables Ar1, L1, R1, R2, R3, R4, R5, Y1, Y2, and Y3, are as defined in the description, which are useful for treating disorders caused by or exacerbated by vanilloid receptor activity.

  本申请涉及作为 TRPV1 拮抗剂并具有式（I）的化合物：其中变量 Ar1、L1、R1、R2、R3、R4、R5、Y1、Y2 和 Y3 如描述中所定义，这些化合物可用于治疗由香草素受体活性引起或加剧的疾病。
• .alpha.2-Adrenergic agonists/antagonists: the synthesis and structure-activity relationships of a series of indolin-2-yl and tetrahydroquinolin-2-yl imidazolines
  作者：Dennis J. Hlasta、Daniel Luttinger、Mark H. Perrone、Marla J. Silbernagel、Susan J. Ward、Dean R. Haubrich

  DOI：10.1021/jm00392a005

  日期：1987.9

  The synthesis and alpha 2-adrenergic activity of a series of indolin-2-yl and tetrahydroquinolin-2-yl imidazolines are described. The indolin-2-yl imidazoline 4b was found to possess potent alpha 2-adrenergic agonist and antagonist activity. The modification of the substituents on the indoline ring of 4b has led to the separation of these activities. Substitution on the aromatic ring of 4b with halogen or increasing the size of the N-alkyl substituent of 4b gave alpha 2-adrenergic antagonists without agonist activity. The N-allylindoline 4d is more potent than idazoxan in vitro and is equipotent in vivo, but is less receptor selective (alpha 2 vs. alpha 1) than idazoxan. The cis-1,3-dimethylindolin-2-yl imidazoline 6a is an alpha 2-adrenergic agonist equal in potency to clonidine in vitro, while the trans-1,3-dimethylindolin-2-yl imidazoline 6b is a moderately potent alpha 2-adrenergic antagonist.