1-(2-methoxy-ethyl)-3-{1-[(S)-3-(5-methoxy-2-methyl-phenoxy)-4-methyl-pentyl]-piperidin-4-yl}-1,3-dihydro-benzimidazol-2-one | 478613-76-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-(2-methoxy-ethyl)-3-{1-[(S)-3-(5-methoxy-2-methyl-phenoxy)-4-methyl-pentyl]-piperidin-4-yl}-1,3-dihydro-benzimidazol-2-one
• 英文别名: 1-(2-methoxyethyl)-3-[1-[(3S)-3-(5-methoxy-2-methylphenoxy)-4-methylpentyl]piperidin-4-yl]benzimidazol-2-one
• CAS: 478613-76-2
• 化学式: C₂₉H₄₁N₃O₄
• 分子量: 495.662
• InChiKey: LTMJVVWUKDXQNB-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-溴乙基甲基醚 、 1-(1-(3-(5-methoxy-2-methylphenoxy)-4-methylpentyl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one 在 CHIRALPAK AD 作用下， 以 异丙醇 为溶剂， 生成 1-(2-methoxy-ethyl)-3-{1-[(R)-3-(5-methoxy-2-methyl-phenoxy)-4-methyl-pentyl]-piperidin-4-yl}-1,3-dihydro-benzimidazol-2-one 、 1-(2-methoxy-ethyl)-3-{1-[(S)-3-(5-methoxy-2-methyl-phenoxy)-4-methyl-pentyl]-piperidin-4-yl}-1,3-dihydro-benzimidazol-2-one
  参考文献：
  名称：

  N -3取代的苯氧丙基哌啶苯并咪唑-2-酮衍生物，有效和选择性的NOP激动剂的不对称合成

  摘要：

  有效的选择性NOP激动剂2-（3- {1- [3-（5-甲氧基-2-甲基-苯氧基）-4-甲基-戊基]-哌啶-4-基} -2-氧-的不对称合成开发了2，3-二氢苯并咪唑-1-基）-N-甲基-乙酰胺和类似物。关键步骤是使用温和的Noyori型不对称氢化实现手性还原乙酸甲基异丁酯。

  DOI：

  10.1016/j.tet.2008.01.125

文献信息

• [EN] 1-(3-PHENYLOXYPROPYL)PIPERIDINE DERIVATIVES<br/>[FR] DERIVES DE 1-(3-PHENYLOXYPROPYL)PIPERIDINE
  申请人：AKZO NOBEL NV

  公开号：WO2002100861A1

  公开（公告）日：2002-12-19

  The present invention relates to 1(3-phenyloxypropyl)-piperidine derivative having general Formula (I), wherein R1 is (C1-6)alkyl or (C4-8)cycloalkyl or phenyl, optionally substituted with (C1-6)alkyl, (C1-6)alkyloxy or halogen; R2 is H or (C1-6)alkyl; or R1 and R2 form together with the carbon atom to which they are bound (C4-8)cycloalkyl, optionally substitutes with (C1-6)alkyloxy or halogen; R3 is H, OH, (C1-6)alkyloxy or (C1-6)alkylcarbonyloxy; R4 represents 1-5 substituents independently selected from H, (C1-6)alkyl, (C1-6)alkyloxy and halogen; Y represents (a), (b) and Z is H; or Y and Z together with the carbon atom to which they are bound represent the spiro atom in the spiro atom in the spiro system formed with (c) *represents the spiro carbon atom; R6 is H, (C1-6)alkyl or (CO)n-(CH2)m-R12; n is 0 or 1; m is 1-4; R8 and R10 are independently H or(C1-6)alkyl; R7, R9 and R11 are independently H, (C1-6)alkyl, (C1-6)alkyloxy or halogen; R12 is hydroxy, (C1-4)alkyloxy, (C1-4)alkylthio, (C1-4)alkyloxycarbonyl, (C1-4)alkylcarbonyloxy, 2-tetrahydrofuranyl, 4-morpholinyl or di(C1-4)alkylamino; or a pharmaceutically acceptable salt thereof. The present invention also relates to pharmaceutical compositions comprising said derivatives, as well as to the use of these 1-(3-phenyloxypropyl)-piperidine derivatives in therapy.
• Asymmetric synthesis of N-3 substituted phenoxypropyl piperidine benzimidazol-2-one derivatives, potent and selective NOP agonists
  作者：John K. Clark、Philip S. Jones、Ronald Palin、Georgina Rosair、Mark Weston

  DOI：10.1016/j.tet.2008.01.125

  日期：2008.3

  The asymmetric synthesis of the potent selective NOP agonist 2-(3-1-[3-(5-methoxy-2-methyl-phenoxy)-4-methyl-pentyl]-piperidin-4-yl}-2-oxo-2,3-dihydro-benzimidazol-1-yl)-N-methyl-acetamide and analogues was developed. The key step, chiral reduction of methyl isobutyryl acetate, was achieved using a mild Noyori-type asymmetric hydrogenation.

  有效的选择性NOP激动剂2-（3- 1- [3-（5-甲氧基-2-甲基-苯氧基）-4-甲基-戊基]-哌啶-4-基} -2-氧-的不对称合成开发了2，3-二氢苯并咪唑-1-基）-N-甲基-乙酰胺和类似物。关键步骤是使用温和的Noyori型不对称氢化实现手性还原乙酸甲基异丁酯。