(R)-9-(1-phenylethyl)aminoanthracene | 851512-15-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (R)-9-(1-phenylethyl)aminoanthracene
• 英文别名: 9-[(R)-N-α-methylbenzylamino]anthracene；N-[(1R)-1-phenylethyl]anthracen-9-amine
• CAS: 851512-15-7
• 化学式: C₂₂H₁₉N
• 分子量: 297.4
• InChiKey: RBQURHBOSJAGMB-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-9-(1-phenylethyl)aminoanthracene 在 三氟化硼乙醚 、 氮气 、 三乙基硼氢化锂 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 51.0h， 生成
  参考文献：
  名称：

  A new, chiral aminoanthracene for the Diels–Alder/retro-Diels–Alder sequence in lactam and butenolide synthesis

  摘要：

  9-(2-Phenylethyl)aminoanthracene has been prepared and used as a template in the Diels-Alder/retro-Diels-Alder sequence to produce alpha,beta-butenolides and alpha,beta-unsaturated lactams. In this sequence the aminoanthracene serves as a stereo- and regiocontrolling chaperone in guiding maleic anhydride or N-alkylmaleimides through transformations to the butenolide or lactam targets. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.046
• 作为产物：
  描述：

  9-溴蒽 、 R(+)-alpha-甲基苄胺 在 tris(dibenzylideneacetone)dipalladium (0) R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 生成 (R)-9-(1-phenylethyl)aminoanthracene
  参考文献：
  名称：

  A new, chiral aminoanthracene for the Diels–Alder/retro-Diels–Alder sequence in lactam and butenolide synthesis

  摘要：

  9-(2-Phenylethyl)aminoanthracene has been prepared and used as a template in the Diels-Alder/retro-Diels-Alder sequence to produce alpha,beta-butenolides and alpha,beta-unsaturated lactams. In this sequence the aminoanthracene serves as a stereo- and regiocontrolling chaperone in guiding maleic anhydride or N-alkylmaleimides through transformations to the butenolide or lactam targets. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.046

文献信息

• Asymmetric control in Diels–Alder cycloadditions of chiral 9-aminoanthracenes by relay of stereochemical information
  作者：Harry Adams、Ramadan A. Bawa、Keith G. McMillan、Simon Jones

  DOI：10.1016/j.tetasy.2007.04.012

  日期：2007.5

  cycloadditions with N-methyl maleimide and maleic anhydride. Excellent reactivity was achieved with good levels of diastereoselectivity, through a favourable combination of electrostatic and hydrogen bonding effects. Trial studies of the retro Diels–Alder reaction of these cycloadducts were also performed.

  描述了两种合成手性9-氨基蒽的方法。首先，通过向BF 3 ·OEt 2促进的亚胺上亲核添加有机锂试剂，出乎意料地提供了稳定的氨基硼烷产品。第二种方法，使用钯催化的交叉偶联，对于伯胺而言更为成功，关键的9-（α-甲基苄基氨基）蒽与N-甲基马来酰亚胺和顺丁烯二酸酐进行环加成反应。通过静电和氢键作用的良好结合，以优异的非对映选择性实现了出色的反应性。还对这些环加合物的逆狄尔斯-阿尔德反应进行了试验研究。
• A new, chiral aminoanthracene for the Diels–Alder/retro-Diels–Alder sequence in lactam and butenolide synthesis
  作者：Amitav Sanyal、Qian Yuan、John K. Snyder

  DOI：10.1016/j.tetlet.2005.02.046

  日期：2005.4

  9-(2-Phenylethyl)aminoanthracene has been prepared and used as a template in the Diels-Alder/retro-Diels-Alder sequence to produce alpha,beta-butenolides and alpha,beta-unsaturated lactams. In this sequence the aminoanthracene serves as a stereo- and regiocontrolling chaperone in guiding maleic anhydride or N-alkylmaleimides through transformations to the butenolide or lactam targets. (c) 2005 Elsevier Ltd. All rights reserved.