2-<2-(N,N-diethylamino)ethoxy>-1,4,5,6,7,8-hexahydro-1-propylnaphthalene | 174464-53-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-<2-(N,N-diethylamino)ethoxy>-1,4,5,6,7,8-hexahydro-1-propylnaphthalene
• 英文别名: N,N-diethyl-2-[(1-propyl-1,4,5,6,7,8-hexahydronaphthalen-2-yl)oxy]ethanamine
• CAS: 174464-53-0
• 化学式: C₁₉H₃₃NO
• 分子量: 291.477
• InChiKey: VCVGCCUCDQSQAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-<2-(N,N-diethylamino)ethoxy>-1,4,5,6,7,8-hexahydro-1-propylnaphthalene 在 盐酸 、 氨 、 lithium 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 叔丁醇 为溶剂， 反应 3.25h， 生成 (1S^*,4aS^*,8aR^*)-1,4,4a,5,6,7,8,8a-octahydro-1-propyl-2-(trimethylsilyloxy)naphthalene
  参考文献：
  名称：

  Synthesis and Characterization of In-Plane and Out-of-Plane Enone−Lewis Acid Complexes:  Implications for Diels−Alder Reactions¹

  摘要：

  In order to determine the reactive geometries of enone-TiCl4 complexes in Diels-Alder reactions compounds 1a . TiCl4 and 1b . TiCl4 were prepared. A crystal structure of 1a . TiCl4 confirmed that the titanium in this complex has the desired out;of-plane geometry, with a Ti-O=C-C dihedral angle of 57.6 degrees, a value remarkably similar to dihedral angles found in simple carbocyclic compounds. Difference NOE studies support a similar geometry in solution. The magnitudes of key H-1 and C-13 NMR chemical shift changes upon complex formation indicate that the out-of-plane TiCl4 in 1a . TiCl4 is a stronger Lewis acid than the in-plane TiCl4 of 1e . TiCl4. These results are further supported by the changes in carbonyl stretching frequencies upon complex formation, with a Delta nu(C-O) for 1a . TiCl4 which is 24 cm(-1) larger than that for 1e . TiCl4. Expectations of heightened reactivity for 1a . TiCl4 as compared to 1e . TiCl4 have been confirmed; the former complex undergoes Diels-Alder reactions with cyclopentadiene 15 times more rapidly than the latter, despite being disfavored on a thermodynamic basis. These results suggest that the commonly held assumption of an in-place reactive geometry for titanium-based Lewis acid-mediated Diels-Aider reactions may be in error.

  DOI：

  10.1021/jo9518112
• 作为产物：
  描述：

  2-二乙氨基氯乙烷盐酸盐 在 氢氧化钾 、 正丁基锂 、 乙醇 、 氨 、 lithium 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.25h， 生成 2-<2-(N,N-diethylamino)ethoxy>-1,4,5,6,7,8-hexahydro-1-propylnaphthalene
  参考文献：
  名称：

  Synthesis and Characterization of In-Plane and Out-of-Plane Enone−Lewis Acid Complexes:  Implications for Diels−Alder Reactions¹

  摘要：

  In order to determine the reactive geometries of enone-TiCl4 complexes in Diels-Alder reactions compounds 1a . TiCl4 and 1b . TiCl4 were prepared. A crystal structure of 1a . TiCl4 confirmed that the titanium in this complex has the desired out;of-plane geometry, with a Ti-O=C-C dihedral angle of 57.6 degrees, a value remarkably similar to dihedral angles found in simple carbocyclic compounds. Difference NOE studies support a similar geometry in solution. The magnitudes of key H-1 and C-13 NMR chemical shift changes upon complex formation indicate that the out-of-plane TiCl4 in 1a . TiCl4 is a stronger Lewis acid than the in-plane TiCl4 of 1e . TiCl4. These results are further supported by the changes in carbonyl stretching frequencies upon complex formation, with a Delta nu(C-O) for 1a . TiCl4 which is 24 cm(-1) larger than that for 1e . TiCl4. Expectations of heightened reactivity for 1a . TiCl4 as compared to 1e . TiCl4 have been confirmed; the former complex undergoes Diels-Alder reactions with cyclopentadiene 15 times more rapidly than the latter, despite being disfavored on a thermodynamic basis. These results suggest that the commonly held assumption of an in-place reactive geometry for titanium-based Lewis acid-mediated Diels-Aider reactions may be in error.

  DOI：

  10.1021/jo9518112

文献信息

• Synthesis and Characterization of In-Plane and Out-of-Plane Enone−Lewis Acid Complexes:  Implications for Diels−Alder Reactions¹
  作者：D. K. Singh、James B. Springer、Patricia A. Goodson、Robert C. Corcoran

  DOI：10.1021/jo9518112

  日期：1996.1.1

  In order to determine the reactive geometries of enone-TiCl4 complexes in Diels-Alder reactions compounds 1a . TiCl4 and 1b . TiCl4 were prepared. A crystal structure of 1a . TiCl4 confirmed that the titanium in this complex has the desired out;of-plane geometry, with a Ti-O=C-C dihedral angle of 57.6 degrees, a value remarkably similar to dihedral angles found in simple carbocyclic compounds. Difference NOE studies support a similar geometry in solution. The magnitudes of key H-1 and C-13 NMR chemical shift changes upon complex formation indicate that the out-of-plane TiCl4 in 1a . TiCl4 is a stronger Lewis acid than the in-plane TiCl4 of 1e . TiCl4. These results are further supported by the changes in carbonyl stretching frequencies upon complex formation, with a Delta nu(C-O) for 1a . TiCl4 which is 24 cm(-1) larger than that for 1e . TiCl4. Expectations of heightened reactivity for 1a . TiCl4 as compared to 1e . TiCl4 have been confirmed; the former complex undergoes Diels-Alder reactions with cyclopentadiene 15 times more rapidly than the latter, despite being disfavored on a thermodynamic basis. These results suggest that the commonly held assumption of an in-place reactive geometry for titanium-based Lewis acid-mediated Diels-Aider reactions may be in error.