cis-3-ethyl-4-piperidineacetic acid ethyl ester

• 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: cis-3-ethyl-4-piperidineacetic acid ethyl ester
• 英文别名: ethyl rel(3S,4R)-3-ethylpiperidine-4-acetate((+/-)cincholoipon ethyl ester)；(+/-)-(cis-3-ethyl-[4]piperidyl)-acetic acid ethyl ester；(+/-)-(cis-3-Aethyl-[4]piperidyl)-essigsaeure-aethylester；ethyl 2-[(3S,4R)-3-ethylpiperidin-4-yl]acetate
• 化学式: C₁₁H₂₁NO₂
• 分子量: 199.293
• InChiKey: ZMYQHFQMRLPPRB-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-3-ethyl-4-piperidineacetic acid ethyl ester 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 mercury(II) diacetate 、 edetate disodium 作用下， 以 1,4-二氧六环 为溶剂， 生成 (+/-)-corynantheidol
  参考文献：
  名称：

  1,6-Dihydro-3(2H)-pyridinones as synthetic intermediates. Stereoselective synthesis of (.+-.)-corynantheidol and (.+-.)-quinine.

  摘要：

  描述了一种从乙基1,6-二氢-3(2H)-吡啶酮-1-羧酸酯（1）开始制备顺式3,4-二取代哌啶化合物的新合成方法。通过应用这种方法，成功实现了（±）-柯楠茶碱（3）的全合成和（±）-奎宁（4）的形式合成。

  DOI：

  10.1248/cpb.30.1925
• 作为产物：
  描述：

  benzyl rel(3S,4R)-4-ethoxycarbonylmethyl-3-(2-hydroxyethyl)-piperidine-1-carboxylate 在 palladium on activated charcoal 吡啶 、 氢气 、 sodium iodide 、 锌 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 17.0h， 生成 cis-3-ethyl-4-piperidineacetic acid ethyl ester
  参考文献：
  名称：

  1,6-Dihydro-3(2H)-pyridinones. VIII. Total synthesis of (.+-.)-corynantheidol and formal synthesis of (.+-.)-quinine.

  摘要：

  顺式-3, 4-二取代哌啶化合物（2 和 3）是由 3-(1,3-二氧戊环-2-基甲基)-1, 2, 3, 6-四氢吡啶-1-甲酸苄酯 (13) 通过酮 (17) 立体选择性地制备的。此外，还分别从哌啶 2 和哌啶 3 中完全合成了 (±)-corynantheidol (4)，并正式合成了 (±)-quinine (5)。

  DOI：

  10.1248/cpb.31.1551

文献信息

• 1,6-Dihydro-3(2H)-pyridinones as synthetic intermediates. Stereoselective synthesis of (.+-.)-corynantheidol and (.+-.)-quinine.
  作者：Takeshi Imanishi、Makoto Inoue、Yasuaki Wada、Miyoji Hanaoka

  DOI：10.1248/cpb.30.1925

  日期：——

  A new synthetic method is described for the cis-3, 4-disubstituted piperidine compounds starting from ethyl 1, 6-dihydro-3 (2H)-pyridinone-1-carboxylate (1). Total synthesis of (±)-corynantheidol (3) and formal synthesis of (±)-quinine (4) were accomplished by an application of this method.

  描述了一种从乙基1,6-二氢-3(2H)-吡啶酮-1-羧酸酯（1）开始制备顺式3,4-二取代哌啶化合物的新合成方法。通过应用这种方法，成功实现了（±）-柯楠茶碱（3）的全合成和（±）-奎宁（4）的形式合成。
• Piperidine Derivatives. XVI. C-Alkylation of 1-Benzoyl-3-carbethoxy-4-piperidone. Synthesis of Ethyl 3-Ethyl-4-piperidylacetate (dl-Ethyl Cincholoiponate)
  作者：Gilbert Stork、S. M. McElvain

  DOI：10.1021/ja01210a041

  日期：1946.6

  309-314' d.: 312',11 316' d.la)). The product weighed 0.49 g. (84%) and decolorized aqueous permanganate immediately. Anal. Calcd. for CJ3loOnNCl: C1, 21.67. Found: C1, 21.54. The p-toluenesulfonyl derivative of guvacine, prepared according to Freudenberg," melted at 166-167' (reported,

  已经重新固化。苯甲酸在试管的较冷部分以升华物的形式出现，并且可以闻到微弱的苯甲酰氯气味。冷却后，将氯仿加入剩余的固体中以溶解任何苯甲酸和不变的IX；未被该溶剂溶解的未溶解的白色固体是盐酸番红花碱，它基本上是纯的，mp 304405'd。先前变暗（先前报道的熔点：309-314' d.：312',11 316' d.la））。产物重0.49g。(84%) 并立即脱色高锰酸盐水溶液。肛门。计算。对于 CJ3loOnNCl：C1，21.67。发现：C1，21.54。根据科德宝公司制备的番红花碱的对甲苯磺酰基衍生物”在 166-167' 熔化（据报道，
• Stereodivergent Synthesis of Enantiopure <i>cis</i>- and <i>trans</i>-3-Ethyl-4-piperidineacetates
  作者：Mercedes Amat、Maria Pérez、Núria Llor、Joan Bosch

  DOI：10.1021/ol0263245

  日期：2002.8.1

  [GRAPHICS]Starting from a common chiral bicyclic lactam 11, enantiopure trans- or cis-3-ethyl-4-piperidineacetate derivatives are obtained by conjugate addition of an enolate or a cuprate to the unsaturated lactams 12 or 18, respectively.
• New N-(benzhydryloxyalkyl)-4-(carboxy/carbamoylmethyl) piperidine derivatives with antidepressant activity
  作者：Y El Ahmad、P Maillet、E Laurent、A Talab、JF Teste、MJ Cédat、PY Fiez-Vandal、R Dokhan、R Ollivier

  DOI：10.1016/s0223-5234(97)83972-4

  日期：1997.1

  Several benzhydryloxylalkylpiperidine derivatives were prepared with the aim of obtaining new antidepressant compounds. The influence of the length of the aliphatic chain and of aromatic and piperidine ring substitutions was studied. The pharmacological activity of compounds was investigated in vivo by means of a screening comprising four pharmacological tests: antagonism of reserpine and apomorphine hypothermia; increase of yohimbine induced mortality; and antagonism of immobility in tail suspension test. An in-depth pharmacological study was performed with the more active compounds and a binding study to serotonin (5-HT), norepinephrine (NE) and dopamine (DA) reuptake sites was performed for the preferred compounds. The most active compounds [+], [-]-cis-31, 32 and 46 exhibited an interesting psychopharmacological profile after intraperitoneal administration. This profile was confirmed by the oral route for 31 and 46. In vitro, these compounds showed a non-selective inhibition of DA, NE and 5-HT uptake.
• 1,6-Dihydro-3(2H)-pyridinones. VIII. Total synthesis of (.+-.)-corynantheidol and formal synthesis of (.+-.)-quinine.
  作者：TAKESHI IMANISHI、MAKOTO INOUE、YASUAKI WADA、MIYOJI HANAOKA

  DOI：10.1248/cpb.31.1551

  日期：——

  cis-3, 4-Disubstituted piperidine compounds (2 and 3) were stereoselectively prepared from benzyl 3-(1, 3-dioxolan-2-ylmethyl)-1, 2, 3, 6-tetrahydropyridine-1-carboxylate (13) via the ketone (17). A total synthesis of (±)-corynantheidol (4) and a formal synthesis of (±)-quinine (5) have also been achieved from the piperidines 2 and 3, respectively.

  顺式-3, 4-二取代哌啶化合物（2 和 3）是由 3-(1,3-二氧戊环-2-基甲基)-1, 2, 3, 6-四氢吡啶-1-甲酸苄酯 (13) 通过酮 (17) 立体选择性地制备的。此外，还分别从哌啶 2 和哌啶 3 中完全合成了 (±)-corynantheidol (4)，并正式合成了 (±)-quinine (5)。