N-(3,5-dibromo-4-hydroxybenzyl)-8-oxoadenine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N-(3,5-dibromo-4-hydroxybenzyl)-8-oxoadenine
• 英文别名: aplidiamine；2,6-Dibromo-4-[[(8-oxo-7,9-dihydropurin-1-ium-6-yl)amino]methyl]phenolate
• 化学式: C₁₂H₉Br₂N₅O₂
• 分子量: 415.044
• InChiKey: FXJCPCLEPGZXDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  99.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 N-(3,5-dibromo-4-hydroxybenzyl)-8-oxoadenine 以 甲醇 、 二氯甲烷 为溶剂， 生成 6-(3,5-Dibromo-4-methoxy-benzylamino)-7,9-dimethyl-7,9-dihydro-purin-8-one 、 (3,5-Dibromo-4-methoxy-benzyl)-(8-methoxy-9-methyl-9H-purin-6-yl)-amine 、 (3,5-Dibromo-4-methoxy-benzyl)-(8-methoxy-9H-purin-6-yl)-amine 、 6-(3,5-Dibromo-4-methoxy-benzylamino)-9-methyl-7,9-dihydro-purin-8-one
  参考文献：
  名称：

  Aplidiamine, a unique zwitterionic benzyl hydroxyadenine from the Western Australian marine ascidian Aplidiopsis sp.

  摘要：

  Aplidiamine (1), a unique zwitterionic benzyl substituted hydroxyadenine, has been isolated from the marine ascidian Aplidiopsis sp. collected in Western Australia. The structure of aplidiamine was determined by spectral analysis of the natural product and of several derivatives produced by diazomethane methylation. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00003-8
• 作为产物：
  描述：

  7,8-dihydro-8-oxo-2'-deoxyadenosine 在 盐酸 、 sodium hydroxide 作用下， 反应 1.0h， 生成 N-(3,5-dibromo-4-hydroxybenzyl)-8-oxoadenine
  参考文献：
  名称：

  Syntheses of the marine ascidian purine aplidiamine and its 9-β-d-ribofuranoside

  摘要：

  The title nucleoside 9 was synthesized by alkylation of 8-oxoadenosine (7) with 4-benzyloxy-3,5 dibromobenzyl bromide, followed by Dimroth rearrangement and acid hydrolysis. 2'-Deoxy version of this reaction sequence accomplished the first synthesis of aplidiamine (6). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00880-6

文献信息

• Synthesis and Structure of the Marine Ascidian 8-Oxoadenine Aplidiamine.
  作者：Taisuke ITAYA、Yoshitaka HOZUMI、Tae KANAI、Tomohisa OHTA

  DOI：10.1248/cpb.47.1297

  日期：——

  Alkylation of 8-oxoadenosine (13) with 4-benzyloxy-3, 5-dibromobenzyl bromide (20), followed by Dimroth rearrangement and acid hydrolysis, provided N-(3, 5-dibromo-4-hydroxybenzyl)-8-oxoadenosine (15). The 2'-deoxy version of this reaction sequence accomplished the first synthesis of N-(3, 5-dibromo-4-hydroxybenzyl)-8-oxodenine (16), which is the correct expression for marine ascidian purine aplidiamine.

  8-氧代腺苷 (13) 用 4-苄氧基-3, 5-二溴苄基溴 (20) 烷基化，然后进行 Dimroth 重排和酸水解，得到 N-(3, 5-二溴-4-羟基苄基)-8-氧代腺苷 ( 15）。该反应序列的 2'-脱氧版本首次合成了 N-(3, 5-二溴-4-羟基苄基)-8-氧化腺嘌呤 (16)，这是海洋海鞘嘌呤 aplidiamine 的正确表达。
• Syntheses of the marine ascidian purine aplidiamine and its 9-β-d-ribofuranoside
  作者：Taisuke Itaya、Yoshitaka Hozumi、Tae Kanai、Tomihisa Ohta

  DOI：10.1016/s0040-4039(98)00880-6

  日期：1998.6

  The title nucleoside 9 was synthesized by alkylation of 8-oxoadenosine (7) with 4-benzyloxy-3,5 dibromobenzyl bromide, followed by Dimroth rearrangement and acid hydrolysis. 2'-Deoxy version of this reaction sequence accomplished the first synthesis of aplidiamine (6). (C) 1998 Elsevier Science Ltd. All rights reserved.
• Aplidiamine, a unique zwitterionic benzyl hydroxyadenine from the Western Australian marine ascidian Aplidiopsis sp.
  作者：Heonjoong Kang、William Fenical

  DOI：10.1016/s0040-4039(97)00003-8

  日期：1997.2

  Aplidiamine (1), a unique zwitterionic benzyl substituted hydroxyadenine, has been isolated from the marine ascidian Aplidiopsis sp. collected in Western Australia. The structure of aplidiamine was determined by spectral analysis of the natural product and of several derivatives produced by diazomethane methylation. (C) 1997, Elsevier Science Ltd.