6-bromo-N-(γ-carboxypropyl)-3,4-dihydro-4-methylspiro[quinoline-2,1'-cyclohexane] | 522592-85-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-bromo-N-(γ-carboxypropyl)-3,4-dihydro-4-methylspiro[quinoline-2,1'-cyclohexane]
• 英文别名: 4-(6-Bromo-4-methylspiro[3,4-dihydroquinoline-2,1'-cyclohexane]-1-yl)butanoic acid
• CAS: 522592-85-4
• 化学式: C₁₉H₂₆BrNO₂
• 分子量: 380.325
• InChiKey: FPKCEDRJXHNJQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-bromo-N-(γ-carboxypropyl)-3,4-dihydro-4-methylspiro[quinoline-2,1'-cyclohexane] 在 PPA 作用下， 以58%的产率得到7-bromo-3-methyl-4-(2-oxopyrrolidinyl-1)spiro[indane-1,1'-cyclohexane]
  参考文献：
  名称：

  Chemistry of N-functionalized spirodihydroquinolines. Unusual access to the 3-methyl-4-(2-oxo-pyrrolidinyl-1)spiro[indane-1,1′-cyclohexanes] from 1-(3-cyanopropyl)-3,4-dihydrospiro[quinoline-2,1′-cyclohexanes]

  摘要：

  The transformation of N-substituted 3,4-dihydrospiro[quinoline-2,1'-cyclohexanes] 2 and 3 has been examined in strong acid media, at elevated temperature. It was demonstrated that the N-(gamma-cyanopropyl) spirodihydroquinolines 2 in the presence of concentrated sulfuric acid or PPA underwent hydrolysis affording the gamma-aminoacids 3. The spirodihydroquinoline ring rearrangement readily produces 4-(2-oxopyrrolidinyl-1)spiro[indane-1,1'-cyclohexanes] 5 in good yields. The structures of all synthesized compounds were established by means of homonuclear and inverse-detected 2D NMR experiments. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01476-x
• 作为产物：
  描述：

  1,2,3,4-tetrahydro-4-methyl-6-bromospiro 在 硫酸 、 sodium carbonate 、 potassium iodide 作用下， 以 正丁醇 为溶剂， 生成 6-bromo-N-(γ-carboxypropyl)-3,4-dihydro-4-methylspiro[quinoline-2,1'-cyclohexane]
  参考文献：
  名称：

  Chemistry of N-functionalized spirodihydroquinolines. Unusual access to the 3-methyl-4-(2-oxo-pyrrolidinyl-1)spiro[indane-1,1′-cyclohexanes] from 1-(3-cyanopropyl)-3,4-dihydrospiro[quinoline-2,1′-cyclohexanes]

  摘要：

  The transformation of N-substituted 3,4-dihydrospiro[quinoline-2,1'-cyclohexanes] 2 and 3 has been examined in strong acid media, at elevated temperature. It was demonstrated that the N-(gamma-cyanopropyl) spirodihydroquinolines 2 in the presence of concentrated sulfuric acid or PPA underwent hydrolysis affording the gamma-aminoacids 3. The spirodihydroquinoline ring rearrangement readily produces 4-(2-oxopyrrolidinyl-1)spiro[indane-1,1'-cyclohexanes] 5 in good yields. The structures of all synthesized compounds were established by means of homonuclear and inverse-detected 2D NMR experiments. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01476-x

文献信息

• Chemistry of N-functionalized spirodihydroquinolines. Unusual access to the 3-methyl-4-(2-oxo-pyrrolidinyl-1)spiro[indane-1,1′-cyclohexanes] from 1-(3-cyanopropyl)-3,4-dihydrospiro[quinoline-2,1′-cyclohexanes]
  作者：Vladimir Kouznetsov、Alirio Palma、Wilson Rozo、Elena Stashenko、Ali Bahsas、Juan Amaro-Luis

  DOI：10.1016/s0040-4020(02)01476-x

  日期：2003.1

  The transformation of N-substituted 3,4-dihydrospiro[quinoline-2,1'-cyclohexanes] 2 and 3 has been examined in strong acid media, at elevated temperature. It was demonstrated that the N-(gamma-cyanopropyl) spirodihydroquinolines 2 in the presence of concentrated sulfuric acid or PPA underwent hydrolysis affording the gamma-aminoacids 3. The spirodihydroquinoline ring rearrangement readily produces 4-(2-oxopyrrolidinyl-1)spiro[indane-1,1'-cyclohexanes] 5 in good yields. The structures of all synthesized compounds were established by means of homonuclear and inverse-detected 2D NMR experiments. (C) 2003 Elsevier Science Ltd. All rights reserved.