N-(23-hydroxy-11,11-dimethyl-2,10,13-trioxo-3,15-dioxa-9,12-diazatetracyclo[14.10.2.017,22.024,28]octacosa-1(27),16(28),17,19,21,23,25-heptaen-14-yl)acetamide | 136198-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: N-(23-hydroxy-11,11-dimethyl-2,10,13-trioxo-3,15-dioxa-9,12-diazatetracyclo[14.10.2.017,22.024,28]octacosa-1(27),16(28),17,19,21,23,25-heptaen-14-yl)acetamide
• CAS: 136198-02-2
• 化学式: C₂₈H₃₁N₃O₇
• 分子量: 521.57
• InChiKey: SYYOBIHPEGTLCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  38.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  143.06
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  蒽醌-2-羧酸 在 盐酸 、 五氯化磷 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 乙腈 、 苯 为溶剂， 反应 3.5h， 生成 N-(23-hydroxy-11,11-dimethyl-2,10,13-trioxo-3,15-dioxa-9,12-diazatetracyclo[14.10.2.017,22.024,28]octacosa-1(27),16(28),17,19,21,23,25-heptaen-14-yl)acetamide
  参考文献：
  名称：

  Intramolecular photoreaction of synthetic oligopeptide-linked anthraquinone molecules

  摘要：

  Photoreaction of (N-acetylglycyl)oligopeptide-linked anthraquinone molecules was investigated. In an acetonitrile site of glycine residue. The biradical formed was followed by the formation of C-O bonding via radical recombination to produce ring-closure products in high yields (23-58%). A variety of oligopeptide spacers between acetylglycine and anthraquinone moieties were systematically changed, and their photoreactivities were investigated. The isolated ring-closure products showed a site-selectivity in the photoreaction; one of the carbonyl groups of anthraquinone moiety coupled with the methylene group predominantly (the selectivity was 88/12-100/0). The efficiency of the photocyclization was dependent upon the size and the sequence of the oligopeptide spacer. These results showed that the oligopeptide spacer might control the distance and the orientation among the reaction sites, glycine methylene, and anthraquinone carbonyl groups.

  DOI：

  10.1021/jo00049a019

文献信息

• Site-Selective Photocyclization of Acetylglycine–Anthraquinone Molecules
  作者：Kazuhiro Maruyama、Masakazu Hashimoto、Hitoshi Tamiaki

  DOI：10.1246/cl.1991.1455

  日期：1991.8

  5-[(N-Acetylglycyl)amino]pentyl, 5-[(N-acetylglycyl-α-methylalanyl)amino]pentyl, and 5-[(N-acetylglycyl-α-methylalanyl-α-methylalanyl)amino]pentyl anthraquinone-2-carboxylate underwent a photocyclization in an acetonitrile solution to produce efficiently large-sized ring-closure compounds as isolable products. In the photocyclization, high site-selectivity in the carbonyl groups of anthraquinone moiety was first observed.

  5-[(N-乙酰基甘氨酰)氨基]戊基、5-[(N-乙酰基甘氨酰-α-甲基丙氨酰)氨基]戊基和 5-[(N-乙酰基甘氨酰-α-甲基丙氨酰-α-甲基丙氨酰)氨基]戊基蒽醌-2-甲酸酯在乙腈溶液中发生光环化反应，生成了高效的大尺寸闭环化合物作为可分离产物。在光环化过程中，首先观察到蒽醌分子的羰基具有高度的位点选择性。