1-[N-(2,5-cis-dimethyl)pyrrolidinylcarbonyl]naphthalene | 438238-36-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[N-(2,5-cis-dimethyl)pyrrolidinylcarbonyl]naphthalene
• 英文别名: [(2S,5R)-2,5-dimethylpyrrolidin-1-yl]-naphthalen-1-ylmethanone
• CAS: 438238-36-9
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: OVOYCFARQDPQGF-BETUJISGSA-N

物化性质

• 沸点：
  412.5±14.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-[N-(2,5-cis-dimethyl)pyrrolidinylcarbonyl]naphthalene 、 碘甲烷 在 仲丁基锂 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 1.83h， 生成 1-[N-(2,5-cis-dimethyl)pyrrolidinylcarbonyl]-2-methylnaphthalene
  参考文献：
  名称：

  Stereodynamics of Bond Rotation in Tertiary Aromatic Amides

  摘要：

  The degree to which the rotations about the C-N and Ar-CO bonds of aromatic amides occur in a concerted manner was investigated by a variety of NMR and kinetic techniques. Otherwise complex kinetic analyses were simplified by exploiting symmetry and asymmetry in the N-substituents of amides. In 2-unsubstituted 1-naphthamides bearing branched N-substituents, most conformational changes about the amide group were by correlated rotation, though uncorrelated Ar-CO rotation also occurred to some extent. In 2-substituted 1-naphthamides, correlated rotation accounted for all of the Ar-CO rotations, though a significant amount of uncorrelated C-N rotation also occurred. Naphthamides bearing branched N-substituents thus turn out to be efficient molecular gears.

  DOI：

  10.1002/1521-3765(20020315)8:6<1279::aid-chem1279>3.0.co;2-7
• 作为产物：
  描述：

  2,5-己二酮 在 Rh/Al₂O₃ sodium hydroxide 、 氢气 、 碳酸氢铵 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 1-[N-(2,5-cis-dimethyl)pyrrolidinylcarbonyl]naphthalene
  参考文献：
  名称：

  Concerted Rotation in a Tertiary Aromatic Amide: Towards a Simple Molecular Gear

  摘要：

  DOI：

  10.1002/(sici)1521-3773(19980803)37:13/14<1937::aid-anie1937>3.0.co;2-4

文献信息

• Concerted Rotation in a Tertiary Aromatic Amide: Towards a Simple Molecular Gear
  作者：Jonathan Clayden、Jennifer H. Pink

  DOI：10.1002/(sici)1521-3773(19980803)37:13/14<1937::aid-anie1937>3.0.co;2-4

  日期：1998.8.3
• Stereodynamics of Bond Rotation in Tertiary Aromatic Amides
  作者：Ryan A. Bragg、Jonathan Clayden、Gareth A. Morris、Jennifer H. Pink

  DOI：10.1002/1521-3765(20020315)8:6<1279::aid-chem1279>3.0.co;2-7

  日期：2002.3.15

  The degree to which the rotations about the C-N and Ar-CO bonds of aromatic amides occur in a concerted manner was investigated by a variety of NMR and kinetic techniques. Otherwise complex kinetic analyses were simplified by exploiting symmetry and asymmetry in the N-substituents of amides. In 2-unsubstituted 1-naphthamides bearing branched N-substituents, most conformational changes about the amide group were by correlated rotation, though uncorrelated Ar-CO rotation also occurred to some extent. In 2-substituted 1-naphthamides, correlated rotation accounted for all of the Ar-CO rotations, though a significant amount of uncorrelated C-N rotation also occurred. Naphthamides bearing branched N-substituents thus turn out to be efficient molecular gears.