2,6-[1,4-(1,7-naphthylene)-5-oxadecano]-2,3-dihydro-4,7-dimethyl-1H-pyrrolo[3,4-c]pyridine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,6-[1,4-(1,7-naphthylene)-5-oxadecano]-2,3-dihydro-4,7-dimethyl-1H-pyrrolo[3,4-c]pyridine
• 英文别名: 6,24-Dimethyl-14-oxa-2,7-diazapentacyclo[13.6.2.12,5.14,8.018,22]pentacosa-1(21),4,6,8(24),15(23),16,18(22),19-octaene；6,24-dimethyl-14-oxa-2,7-diazapentacyclo[13.6.2.12,5.14,8.018,22]pentacosa-1(21),4,6,8(24),15(23),16,18(22),19-octaene
• 化学式: C₂₄H₂₆N₂O
• 分子量: 358.483
• InChiKey: CCKQGIYTSKSSQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  25.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-氨基-7-萘酚 在 [Rh(cod)2]BARF 、 sodium hydride 、 N,N-二异丙基乙胺 、 1,1'-(1R)-[1,1'-联萘]-2,2'-双[1,1-环己基]膦 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.17h， 生成 2,6-[1,4-(1,7-naphthylene)-5-oxadecano]-2,3-dihydro-4,7-dimethyl-1H-pyrrolo[3,4-c]pyridine
  参考文献：
  名称：

  Enantioselective synthesis of tripodal cyclophanes and pyridinophanes by intramolecular [2+2+2] cycloaddition

  摘要：

  An enantioselective intramolecular [2+2+2] cycloaddition of 2-aminophenol-tethered triynes and diyne-nitriles proceeded using the chiral Rh catalysts, and tripodal cyclophanes and pyridinophanes with a long ansa chain (up to [16]pyridinophane) were obtained in acceptable yield with high to almost perfect ee. In the reaction of triynes, we elucidated that the oxygen atom at the alkyne terminus is essential for the excellent enantioselectivity. For the construction of cage-type molecule, the choice of rigid tether, which connects 1,6-diyne moiety with a side carbon chain having alkyne or cyano group on its terminus, was important, and 8-amino-2-naphthol moiety was also a preferable tether. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.046

文献信息

• Enantioselective synthesis of tripodal cyclophanes and pyridinophanes by intramolecular [2+2+2] cycloaddition
  作者：Takanori Shibata、Mayu Miyoshi、Toshifumi Uchiyama、Kohei Endo、Nobuaki Miura、Kenji Monde

  DOI：10.1016/j.tet.2012.01.046

  日期：2012.3

  An enantioselective intramolecular [2+2+2] cycloaddition of 2-aminophenol-tethered triynes and diyne-nitriles proceeded using the chiral Rh catalysts, and tripodal cyclophanes and pyridinophanes with a long ansa chain (up to [16]pyridinophane) were obtained in acceptable yield with high to almost perfect ee. In the reaction of triynes, we elucidated that the oxygen atom at the alkyne terminus is essential for the excellent enantioselectivity. For the construction of cage-type molecule, the choice of rigid tether, which connects 1,6-diyne moiety with a side carbon chain having alkyne or cyano group on its terminus, was important, and 8-amino-2-naphthol moiety was also a preferable tether. (C) 2012 Elsevier Ltd. All rights reserved.