(S_p)-4-amino-12-methoxy[2.2]paracyclophane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S_p)-4-amino-12-methoxy[2.2]paracyclophane
• 英文别名: 11-Methoxytricyclo[8.2.2.24,7]hexadeca-1(12),4,6,10,13,15-hexaen-5-amine
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: HZBUKOLKDMZPRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S_p)-4-amino-12-methoxy[2.2]paracyclophane 在 sodium tetrahydroborate 、 硫酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis of new alkoxy/sulfonate-substituted carbene precursors derived from [2.2]paracyclophane and their application in the asymmetric arylation of aldehydes

  摘要：

  A series of novel planar chiral alkoxy/sulfonate-substituted carbene precursors have been designed and synthesized. They were used as N-heterocyclic carbene ligands in the Rh-catalyzed asymmetric addition of arylboronic acids to aromatic aldehydes, affording chiral diarylmethanols with high yields and moderate enantioselectivities. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.09.001
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (S_p)-4-amino-12-methoxy[2.2]paracyclophane
  参考文献：
  名称：

  An Efficient Catalyst System for Pd-Catalyzed Amination of [2.2]Paracyclophanyl Bromides

  摘要：

  A practical Buchwald-Hartwig amination of [2.2]paracyclophanyl bromides with benzhydrylideneamine is developed. The method provides a Facile route to a variety of imino and amino [2.2]paracyclophanes that are otherwise not readily synthesized.

  DOI：

  10.1021/jo901310a

文献信息

• Imidazolinium salts derived from amino[2.2]paracyclophane compounds: synthesis and hydrolytic ring-opening
  作者：Kerry-Ann Green、Paul T. Maragh、Kamaluddin Abdur-Rashid、Alan J. Lough、Tara P. Dasgupta

  DOI：10.1016/j.tetlet.2014.07.044

  日期：2014.9

  The synthesis of a series of imidazolinium chlorides containing the [2.2]paracyclophane scaffold is described. Attempts to deprotonate the salts with strong bases resulted in hydrolytic ring-opening and yielded N-formylethylenediamine products rather than the intended free carbenes.

  描述了一系列含有[2.2]对环环烷骨架的咪唑啉鎓氯化物的合成。试图用强碱使该盐去质子化导致水解开环并产生N-甲酰基乙二胺产物而不是预期的游离卡宾。
• Synthesis of new alkoxy/sulfonate-substituted carbene precursors derived from [2.2]paracyclophane and their application in the asymmetric arylation of aldehydes
  作者：Wenzeng Duan、Yudao Ma、Bo Qu、Lei Zhao、Jianqiang Chen、Chun Song

  DOI：10.1016/j.tetasy.2012.09.001

  日期：2012.10

  A series of novel planar chiral alkoxy/sulfonate-substituted carbene precursors have been designed and synthesized. They were used as N-heterocyclic carbene ligands in the Rh-catalyzed asymmetric addition of arylboronic acids to aromatic aldehydes, affording chiral diarylmethanols with high yields and moderate enantioselectivities. (C) 2012 Elsevier Ltd. All rights reserved.
• An Efficient Catalyst System for Pd-Catalyzed Amination of [2.2]Paracyclophanyl Bromides
  作者：Bo Qu、Yudao Ma、Qingshuang Ma、Xiao Liu、Fuyan He、Chun Song

  DOI：10.1021/jo901310a

  日期：2009.9.4

  A practical Buchwald-Hartwig amination of [2.2]paracyclophanyl bromides with benzhydrylideneamine is developed. The method provides a Facile route to a variety of imino and amino [2.2]paracyclophanes that are otherwise not readily synthesized.