6-<2-(N,N-diethylamino)ethoxy>-1,2,3,4-tetrahydronaphthalene | 1025874-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6-<2-(N,N-diethylamino)ethoxy>-1,2,3,4-tetrahydronaphthalene
• 英文别名: N,N-diethyl-2-(5,6,7,8-tetrahydronaphthalen-2-yloxy)ethanamine
• CAS: 1025874-58-1
• 化学式: C₁₆H₂₅NO
• 分子量: 247.381
• InChiKey: GLVCCUBLPMIFAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  6-<2-(N,N-diethylamino)ethoxy>-1,2,3,4-tetrahydronaphthalene 在 乙醇 、 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以95%的产率得到2-<2-(N,N-diethylamino)ethoxy>-1,4,5,6,7,8-hexahydronaphthalene
  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：

  5,6,7,8-四氢-2-萘酚 、 2-二乙氨基氯乙烷盐酸盐 在 氢氧化钾 作用下， 以 水 为溶剂， 以97%的产率得到6-<2-(N,N-diethylamino)ethoxy>-1,2,3,4-tetrahydronaphthalene
  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.