3-氧代哌啶-1-羧酸乙酯 | 61995-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 3-氧代哌啶-1-羧酸乙酯
• 英文名称: ethyl 3-Oxopiperidine-1-carboxylate
• CAS: 61995-19-5
• 化学式: C₈H₁₃NO₃
• 分子量: 171.196
• InChiKey: VWQXCLBFGRMQJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  3-氧代哌啶-1-羧酸乙酯 在 对甲苯磺酸 作用下， 以 乙腈 、 苯 为溶剂， 反应 13.0h， 生成 ethyl 6-<<4-(p-tolylsulfonyl)indolyl>methyl>-1,4-dioxa-7-azaspiro<4.5>decane-7-carboxylate
  参考文献：
  名称：

  某些6-取代的7-甲基-1,4-二氧杂-7-氮杂螺[4.5]癸烷作为潜在的多巴胺激动剂的合成及药理评价。

  摘要：

  通过关键中间体吡咯烷烯胺的烷基化反应，合成了三个在6-位含有苄基，3-吲哚甲基或4-吲哚甲基的7-甲基-1,4-二氧杂-7-氮杂[4.5]癸烷3-氧代哌啶-1-羧酸乙酯。评估了螺癸烷衍生物的体内中枢和外周多巴胺激动剂活性。这些化合物均未显示中枢神经系统活性。然而，4-吲哚甲基类似物在猫心脏加速器神经测定中表现出强力的多巴胺激动剂活性，与阿扑吗啡相比，阿扑吗啡的ID50为0.095摩尔/千克，而阿扑吗啡在同一测定中的ID50为0.0348摩尔/千克。

  DOI：

  10.1021/jm00158a036
• 作为产物：
  描述：

  1-carboethoxy-3-methoxy-5-oxo-3,4-dehydropiperidine 在 三乙基硅烷 、 sodium tetrahydroborate 、 四氯化钛 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 3-氧代哌啶-1-羧酸乙酯
  参考文献：
  名称：

  Chen Ling-Ching; Wang, Eng-Chi; Lin, Jen-Hom, Heterocycles, 1984, vol. 22, # 12, p. 2769 - 2773

  摘要：

  DOI：

文献信息

• Pharmaceutically active compounds
  申请人：Astra Pharmaceuticals Limited

  公开号：US05883102A1

  公开（公告）日：1999-03-16

  Compounds of formula (I) wherein: R.sup.1 and R.sup.19 independently represent hydrogen, alkyl C1-6, alkoxy C1-6, alkylthio C1-6, halogen, hydroxyl or amino; R.sup.2 represents H or alkyl; R.sup.3 represents phenyl, a 6-membered heterocyclic aromatic ring containing one or two nitrogen atoms, or a 5-membered heterocyclic aromatic ring containing 1 to 3 heteroatoms selected from O,N, and S, which phenyl or heterocyclic aromatic ring may be optionally substituted by alkyl C1-6, alkoxy C1-6, haologen, hydroxyl, alkylthio C1-6, cyano, trifluoromethyl, nitro, hydroxymethyl, amino, a group --(CH.sub.2).sub.c NHCO.sub.2 R.sup.10, a group --(CH.sub.2).sub.c NR.sup.5 R.sup.6, or a group --CO.sub.2 R.sup.11 ; or R.sup.3 represents hydrogen or alkyl C1-8, which alkyl group may be optionally substituted by amino or a group --NHCO.sub.2 R.sup.10 ; R.sup.4 represents hydrogen or alkyl C1-6; or R.sup.3 and R.sup.4 taken together represent a group (CH.sub.2).sub.a Z(CH.sub.2).sub.b ; c represents an integer 0 to 2; and pharmaceutically acceptable salts thereof, have been found to be useful as a pharmaceuticals. The compounds may especially be used in the treatment of inflammatory disorders.

  公式(I)的化合物，其中：R 1和R 19独立代表氢、烷基C 1-6、烷氧基C 1-6、烷硫基C 1-6、卤素、羟基或氨基；R 2代表H或烷基；R 3代表苯基，含有一个或两个氮原子的六元杂环芳环，或含有1至3个分别选自O、N和S的杂原子的五元杂环芳环，其中苯基或杂环芳环可任选地被烷基C 1-6、烷氧基C 1-6、卤素、羟基、烷硫基C 1-6、氰基、三氟甲基、硝基、羟甲基、氨基、基团--(CH 2) c NHCO 2 R 10，基团--(CH 2) c NR 5 R 6，或基团--CO 2 R 11取代；或R 3代表氢或烷基C 1-8，其中烷基可任选地被氨基或基团--NHCO 2 R 10取代；R 4代表氢或烷基C 1-6；或R 3和R 4共同代表基团(CH 2) a Z(CH 2) b；c代表整数0至2；及其药物可接受的盐，发现用作药物是有用的。这些化合物特别可用于治疗炎症性疾病。
• N-Heterocyclic-9-xanthenylamines
  申请人：SmithKline Corporation

  公开号：US04005208A1

  公开（公告）日：1977-01-25

  The compounds are N-piperidinyl and pyrrolidinyl-9-xanthenylamines which are inhibitors of gastric acid secretion.

  这些化合物是N-哌啶基和吡咯啉基-9-黄色素胺，它们是胃酸分泌抑制剂。
• Synthesis of bicyclic aza-enones via a lewis acid catalysed Michael-type addition with silyl enol ethers bearing a nitrogen atom.
  作者：Duhamel Pierre、Deyine Abdallah、Poirier Jean-Marie

  DOI：10.1016/s0040-4039(00)79248-3

  日期：1993.6

  Silyl enol ethers bearing a nitrogen atom protected by an electron-withdrawing group give in high yield a Micheal-type addition with hemiacetal vinylog or a mixture of methyl vinyl ketone and an alcohol in the presence of boron trifluoride etherate as a catalyst. The aza-1,5-diketones so prepared can be cyclised leading to aza-enones precursors of some biologycally active structures.

  在三氟化硼醚化物作为催化剂存在下，带有由吸电子基团保护的氮原子的甲硅烷基烯醇醚以半缩醛乙烯醇或甲基乙烯基酮与醇的混合物高收率地得到米歇尔型加成物。如此制备的aza-1,5-二酮可以被环化，产生某些具有生物学活性的结构的aza-烯酮前体。
• An enamine method for the synthesis of 1-azaazulene derivatives. Reactions of troponimines with enamines 1
  作者：Tohru Takayasu、Makoto Nitta

  DOI：10.1039/a809700c

  日期：——

  A short new synthesis of 1-azaazulene derivatives consists of the enamine alkylation of troponimines 4–7 with pyrrolidino enamines, which are derived from cycloalkanones, aliphatic ketones, and heterocyclic ketones, to lead to formal [8 + 2] cycloadducts and subsequent aromatization under the reaction conditions. The reactions are quite general, and N-hydroxy- and N-methoxytroponimines, 4 and 5, are less reactive than N-mesyloxy- and N-tosyloxytroponimines, 6 and 7, which react smoothly even at room temperature. In the reaction of the pyrrolidino enamine, which is derived from cyclopentanone, forcing conditions are required, probably because of ring strain in the [8 + 2] cycloadduct 11a. Furthermore, in the reactions of 4–7 with isomeric mixtures of two pyrrolidino enamines, 15/16 and 20/21, only enamines 15 and 20 can intervene in the cycloaddition reactions, giving 1-azaazulene derivatives. In the context of the reactivity of 4–7 and pyrrolidino enamines, and the selectivity observed in the reactions with isomeric mixtures of enamines, minimal neglect of differential overlap (MNDO) calculations on troponimines 4–7 and pyrrolidino enamines, as well as isomeric mixtures of two enamines, 15/16 and 20/21, were performed to gain further insight into the reactions via a theoretical interpretation based upon frontier molecular orbital theory (FMO). Troponimines 6 and 7 have lower LUMOs and they are more reactive than troponimines 4 and 5; the energy level of the HOMO of the pyrrolidino enamine derived from cyclopentanone is relatively higher as compared to those of other pyrrolidino enamines. Enamines 15 and 20 are less stable and energy levels of the HOMOs are higher as compared with those of the corresponding isomers 16 and 21, respectively.

  一种新的短链合成1-氮基藍烯衍生物的方法包括对4-7号烃基化的氨基萘酮与源自环烷酮、脂肪酮和杂环酮的吡咯烯胺进行反应，从而产生形式上的[8 + 2]环加成物，并在反应条件下随后发生芳香化。这些反应相当普遍，其中N-羟基和N-美克酮基的氨基萘酮4和5的反应性较低，而N-美克酯基和N-苯磺酯基的氨基萘酮6和7则在室温下也能顺利反应。在从环戊酮衍生的吡咯烯胺的反应中，需采取强迫条件，这可能是由于[8 + 2]环加成物11a的环应变。此外，在4-7号与两种异构体的吡咯烯胺混合物15/16和20/21反应时，只有吡咯烯胺15和20能参与环加成反应，生成1-氮基蓝烯衍生物。针对4-7号和吡咯烯胺的反应性，以及在与异构体的吡咯烯胺混合物反应中观察到的选择性，进行了最小忽略微分重叠（MNDO）计算，以进一步深入理解反应，通过基于前沿分子轨道理论（FMO）的理论解释。氨基萘酮6和7的低空态分子轨道（LUMO）更低，反应性比氨基萘酮4和5更强；源自环戊酮的吡咯烯胺的高占据分子轨道（HOMO）能量水平相对较高。吡咯烯胺15和20相对不稳定，其高占据分子轨道的能量水平较对应异构体16和21更高。
• 1,4-Benzodiazepine derivatives
  申请人：SHIONOGI SEIYAKU KABUSHIKI KAISHA

  公开号：EP0111864A1

  公开（公告）日：1984-06-27

  1,4-Benzodiazepine derivatives of the formula: (in which R1 is pyrrolidinyl or piperidinyl each optionally substituted by C1-3 alkyl, phenyl-C1-3 alkyl, C1-5 alkanoyl, or C2-5 alkoxycarbonyl, R2 is hydrogen, hydroxy, or acetoxy, R3 is C1-3 alkyl, phenyl-C1-3 alkyl, or phenyl optionally substituted by one or two halogens, X is hydrogen, halogen, C1-3 alkyl, C1-3 alkoxy, nitro, trifluoromethyl, or di-C1-3 alkyl-amino, and n is 1 or 2) or pharmaceutically acceptable acid addition salts thereof, which are useful as a psychotropic agent such as antidepressant or anxiolytic agent can be prepared from several routes.

  式中的 1,4-苯并二氮杂卓衍生物： (其中 R1 为吡咯烷基或哌啶基，各自任选被 C1-3 烷基、苯基-C1-3 烷基、C1-5 烷酰基或 C2-5 烷氧羰基取代、 R2 是氢、羟基或乙酰氧基、 R3 是 C1-3 烷基、苯基-C1-3 烷基或任选被一个或两个卤素取代的苯基、 X 是氢、卤素、C1-3 烷基、C1-3 烷氧基、硝基、三氟甲基或二-C1-3 烷基氨基，以及 n 是 1 或 2） 或其药学上可接受的酸加成盐，可用作抗抑郁或抗焦虑等精神药物。