4,4a,5,6,7,8-hexahydro-1-propyl-2(3H)-naphthalenone | 18943-04-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4a,5,6,7,8-hexahydro-1-propyl-2(3H)-naphthalenone
• 英文别名: 1-Propyl-4,4a,5,6,7,8-hexahydro-3H-naphthalin-2-on；1-propyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one
• CAS: 18943-04-9
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: DWSNIZNJEHCBCG-UHFFFAOYSA-N

物化性质

• 沸点：
  307.1±9.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,4a,5,6,7,8-hexahydro-1-propyl-2(3H)-naphthalenone 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Geometrical aspects of the activation of enones by titanium tetrachloride: Diels-Alder reactions

  摘要：

  DOI：

  10.1021/ja00023a071
• 作为产物：
  描述：

  1-庚烯-3-酮 在 potassium tert-butylate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 4,4a,5,6,7,8-hexahydro-1-propyl-2(3H)-naphthalenone
  参考文献：
  名称：

  路易斯酸活化酮的几何方面

  摘要：

  测量了两种非对映异构体 1-(甲氧基甲基)-1-丙基十氢萘-2-酮 (1a 和 1e) 的 TiCl 4 配合物与三甲基甲硅烷基氰化物的反应速率，以确定用于羰基活化的优选络合几何结构趋向亲核加成。化合物 1a 包含一个轴向甲氧基甲基，旨在引导 TiCl 4 络合到羰基的 π 系统，而 1e 中的赤道甲氧基甲基将络合引导到平面

  DOI：

  10.1021/ja00038a014

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.
• Geometrical aspects of the activation of ketones by Lewis acids
  作者：Robert C. Corcoran、Junning Ma

  DOI：10.1021/ja00038a014

  日期：1992.6

  The rates of reaction of the TiCl 4 complexes of two diastereomeric 1-(methoxymethyl)-1-propyldecahydronaphthalen-2-ones (1a and 1e) with trimethylsilyl cyanide have been measured for the purpose of determining the preferred complexation geometry for the activation of carbonyls toward nucleophilic addition. Compound 1a incorporates an axial methoxymethyl group which is designed to steer complexation

  测量了两种非对映异构体 1-(甲氧基甲基)-1-丙基十氢萘-2-酮 (1a 和 1e) 的 TiCl 4 配合物与三甲基甲硅烷基氰化物的反应速率，以确定用于羰基活化的优选络合几何结构趋向亲核加成。化合物 1a 包含一个轴向甲氧基甲基，旨在引导 TiCl 4 络合到羰基的 π 系统，而 1e 中的赤道甲氧基甲基将络合引导到平面
• Geometrical aspects of the activation of enones by titanium tetrachloride: Diels-Alder reactions
  作者：Robert C. Corcoran、Junning Ma

  DOI：10.1021/ja00023a071

  日期：1991.11