(R_a*,1'R*/S*)-N,N-diisopropyl-2-[1'-(methylamino)ethyl]-1-naphthamide | 227012-94-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R_a*,1'R*/S*)-N,N-diisopropyl-2-[1'-(methylamino)ethyl]-1-naphthamide
• 英文别名: 2-[1-(methylamino)ethyl]-N,N-di(propan-2-yl)naphthalene-1-carboxamide
• CAS: 227012-94-4
• 化学式: C₂₀H₂₈N₂O
• 分子量: 312.455
• InChiKey: YQMWYTKEZCDKMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 (R_a*,1'R*/S*)-N,N-diisopropyl-2-[1'-(methylamino)ethyl]-1-naphthamide 生成 3-Benzyl-2,3-dimethyl-2,3-dihydro-1H-benzo[e]isoindol-1-one 、 (R_a*,1'R*/S*)-N,N-Diisopropyl-2-{1-[benzyl(methyl)amino]ethyl}-1-naphthamide
  参考文献：
  名称：

  Synthesis of atropisomeric 2-(1-aminoalkyl)-1-naphthamides by stereoselective addition of organolithiums to a 2-imino-1-naphthamide

  摘要：

  Unlike the corresponding aldehydes, 2-(N-methylformimino)-N,N-dialkyl-1-naphthamides react highly atroposelectively with simple organolithium reagents to give atropisomeric amines whose syn stereochemistry is thermodynamically preferred over anti. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00519-5
• 作为产物：
  描述：

  N,N-diisopropyl-2-formyl-1-naphthamide 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 4.0h， 生成 (R_a*,1'R*/S*)-N,N-diisopropyl-2-[1'-(methylamino)ethyl]-1-naphthamide
  参考文献：
  名称：

  Atroposelective attack of nucleophiles on 2-formyl-1-naphthamides and their derivatives: chelation and non-chelation control

  摘要：

  有机金属核苷类物质攻击2-芳醛-1-萘酰胺，生成具有广泛变异的次级醇的非对映选择性。通过仔细选择试剂，可以获得高达99:1的选择性，偏向于反式或顺式对映异构体。醚类和胺类可以从缩醛或亚胺中选择性合成。选择性的方向由Ar–CHO键的反应构象决定，而这又依赖于核苷的配对离子的配位和螯合能力。文中讨论了构象、路易斯酸和螯合/非螯合控制与立体选择性之间的关系。

  DOI：

  10.1039/b000669f

文献信息

• Atroposelective attack of nucleophiles on 2-formyl-1-naphthamides and their derivatives: chelation and non-chelation control
  作者：Jonathan Clayden、Catherine McCarthy、Neil Westlund、Christopher S. Frampton

  DOI：10.1039/b000669f

  日期：——

  Organometallic nucleophiles attack 2-formyl-1-naphthamides to give secondary alcohols with widely varying atroposelectivity. By careful choice of reagent, selectivities of up to >99∶1 in favour of either the anti or the syn atropisomer can be obtained. Ethers and amines may be synthesised atroposelectively from acetals or imines. The sense of the selectivity is determined by the reactive conformation of the Ar–CHO bond, itself dependent on the coordinating and chelating ability of the nucleophile’s counterion. The roles of conformation, Lewis acids, and chelation/non-chelation control in relation to stereoselectivity are discussed.

  有机金属核苷类物质攻击2-芳醛-1-萘酰胺，生成具有广泛变异的次级醇的非对映选择性。通过仔细选择试剂，可以获得高达99:1的选择性，偏向于反式或顺式对映异构体。醚类和胺类可以从缩醛或亚胺中选择性合成。选择性的方向由Ar–CHO键的反应构象决定，而这又依赖于核苷的配对离子的配位和螯合能力。文中讨论了构象、路易斯酸和螯合/非螯合控制与立体选择性之间的关系。
• Synthesis of atropisomeric 2-(1-aminoalkyl)-1-naphthamides by stereoselective addition of organolithiums to a 2-imino-1-naphthamide
  作者：Jonathan Clayden、Neil Westlund、Francis X. Wilson

  DOI：10.1016/s0040-4039(99)00519-5

  日期：1999.4

  Unlike the corresponding aldehydes, 2-(N-methylformimino)-N,N-dialkyl-1-naphthamides react highly atroposelectively with simple organolithium reagents to give atropisomeric amines whose syn stereochemistry is thermodynamically preferred over anti. (C) 1999 Elsevier Science Ltd. All rights reserved.