<1-methyl-4-(ethoxycarbonyl)piperidin-4-yl>acetic acid ethyl ester | 93647-40-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: <1-methyl-4-(ethoxycarbonyl)piperidin-4-yl>acetic acid ethyl ester
• 英文别名: 1-methyl-4-carboxyethyl-4-piperidyl acetic acid ethyl ester；4-ethoxycarbonylmethyl-1-methyl-piperidine-4-carboxylic acid ethyl ester；(1-methyl-4-carboethoxypiperidin-4-yl) acetic acid ethyl ester；(1-Methyl-4-ethoxycarbonyl-piperidyl-4)-essigsaeure-ethylester；Ethyl 4-(2-ethoxy-2-oxoethyl)-1-methylpiperidine-4-carboxylate
• CAS: 93647-40-6
• 化学式: C₁₃H₂₃NO₄
• 分子量: 257.33
• InChiKey: PZOCGVSEAACQRC-UHFFFAOYSA-N

物化性质

• 沸点：
  102-104 °C(Press: 0.15 Torr)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  <1-methyl-4-(ethoxycarbonyl)piperidin-4-yl>acetic acid ethyl ester 在 盐酸 、 sodium acetate 、 乙酸酐 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 2-(dimethylamino)-8-methyl-2,8-diazaspiro<4.5>decane-1,3-dione
  参考文献：
  名称：

  中枢胆碱能药物。三，作为毒蕈碱激动剂的2-烷氧基-2，8-二氮杂螺[4.5]癸烷-1，3-二酮的合成。

  摘要：

  合成了一系列的2-烷氧基-2,8-二氮杂螺[4.5]癸烷-1,3-二酮和相关化合物，并以[3H]哌仑西平和[3H]氧代苯甲酸M作为配体测试了毒蕈碱受体的结合亲和力。还通过豚鼠回肠试验评估了它们的激动活性。发现2-甲氧基-2,8-二氮杂螺[4.5]癸烷-1,3-二酮（1i）是相对M1选择性的激动剂。它以较长的作用时间逆转了CO2引起的被动回避反应的损害，但在低剂量时也表现出外周效应。为了最小化这些副作用，我们提出了将1i与毒蕈碱拮抗剂结合的想法。因此，检查了1i的氨基甲酸酯连接的共轭物（1u）与甲基阿托品。

  DOI：

  10.1248/cpb.40.1177
• 作为产物：
  描述：

  1-甲基-4-哌啶甲酸乙酯 、 溴乙酸乙酯 在 lithium diisopropyl amide 作用下， 生成 <1-methyl-4-(ethoxycarbonyl)piperidin-4-yl>acetic acid ethyl ester
  参考文献：
  名称：

  Synthesis of a new series of 2,8-disubstituted-2,8-diazaspiro[4,5]decan-1-ones as potential muscarinic agonists

  摘要：

  A new series of 2,8-disubstituted-2,8-diazaspiro[4,5]decan-1-ones 2 has been synthesized and tested for affinity towards muscarinic receptors by binding studies in comparison with the model RS-86. The membrane phosphatidylinositol turnover in the presence or absence of carbachol has also been investigated. In both experiments all the new derivatives 2 were found: to be less active than the model; only 5g, which retains the imidic moiety, could approach it in potency. A possible explanation for the lack of activity of this class of compounds is given in terms of the computed interaction energies of the minimized ligand-m(1) receptor complex.

  DOI：

  10.1016/0223-5234(94)90195-3

文献信息

• Azaspiro compounds and their use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04804665A1

  公开（公告）日：1989-02-14

  Azaspiro compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 independently represent hydrogen, a hydrocarbon residue which may have a substituent, or an acyl group which may have a substituent; R.sub.3 represents hydrogen or a hydrocarbon residue which may have a substituent; each of X.sub.1 and X.sub.2 is oxygen or sulfur; Y represents oxygen, sulfur or a group of the formula: --N(R.sub.4)--, wherein R.sub.4 represents hydrogen or a lower alkyl group; m represents 0 or 1; n represents 0 or 1, and its salt are novel compounds, possess excellent brain function-improving action, and are of use as drugs for the prevention and therapy of senile dementia of Alzheimer type, vascular-type dementia and dementia derived from Alzheimer's disease, Pick's disease, Huntington's disease, Creutzfeldt-Jakob's disease, Parkinson's disease and spinocerebellar degeneration.

  Azaspiro化合物的结构式为##STR1##其中R.sub.1和R.sub.2分别代表氢、可能具有取代基的碳氢残基，或者可能具有取代基的酰基；R.sub.3代表氢或者可能具有取代基的碳氢残基；X.sub.1和X.sub.2中的每一个代表氧或者硫；Y代表氧、硫或者具有以下结构的基团：--N(R.sub.4)--，其中R.sub.4代表氢或者较低的烷基基团；m代表0或1；n代表0或1，其盐是新颖的化合物，具有出色的改善脑功能的作用，并可用作预防和治疗老年性阿尔茨海默型痴呆、血管型痴呆以及源自阿尔茨海默病、皮克氏病、亨廷顿病、克雅茨菲尔德-雅各布病、帕金森病和脊髓小脑变性病的药物。
• Azaspiro compounds, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0273659A1

  公开（公告）日：1988-07-06

  Azaspiro compounds of the formula: wherein R₁ and R₂ independently represent hydrgen, a hydrocarbon residue which may have a substituent, or an acyl group which may have a substituent; R₃ represents hydrogen or a hydrocarbon residue which may have a substituent; each of X₁ and X₂ is oxygen or sulfur; Y represents oxygen, sulfur or a group of the formula: -N(R₄)-, wherein R₄ represents hydrogen or a lower alkyl group; m represents 0 or 1; n represents 0 or 1, and its salt are novel compounds, possess excellent brain functionimproving action, and are of use as drugs for the prevention and therapy of senile dementia of Alzheimer type, vascular-type dementia and dementia derived from Alzheimer's disease, Pick's disease, Huntington's disease, Creutzfeldt-­Jakob's disease, Parkinson's disease and spinocerebellar degeneration.

  式中的氮杂环化合物： 其中 R₁ 和 R₂ 独立地代表氢、可具有取代基的烃残基或可具有取代基的酰基；R₃ 代表氢或可具有取代基的烃残基；X₁ 和 X₂ 各自为氧或硫；Y 代表氧、硫或式中的基团：-N(R₄)-，其中 R₄ 代表氢或低级烷基；m 代表 0 或 1；n 代表 0 或 1，其盐是新型化合物，具有优异的改善脑功能的作用，可用作预防和治疗阿尔茨海默型老年痴呆症、血管型痴呆症以及由阿尔茨海默病、皮克病、亨廷顿病、克雅氏病、帕金森病和脊髓小脑变性引起的痴呆症的药物。
• GOTO, GIICHI;NAGAOKA, AKINOBU
  作者：GOTO, GIICHI、NAGAOKA, AKINOBU

  DOI：——

  日期：——
• US4804665A
  申请人：——

  公开号：US4804665A

  公开（公告）日：1989-02-14