6-(苄氧基)-3-溴-2-甲酰基苯基乙基碳酸酯 | 95712-57-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 6-(苄氧基)-3-溴-2-甲酰基苯基乙基碳酸酯
• 英文名称: (3-Bromo-2-formyl-6-phenylmethoxyphenyl) ethyl carbonate
• CAS: 95712-57-5
• 化学式: C₁₇H₁₅BrO₅
• 分子量: 379.207
• InChiKey: SOINYPBQZZJNNK-UHFFFAOYSA-N

物化性质

• 沸点：
  502.7±50.0 °C(Predicted)
• 密度：
  1.444±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(苄氧基)-3-溴-2-甲酰基苯基乙基碳酸酯 在 sodium chlorite 、 sodium dihydrogenphosphate 、 双氧水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 8.0h， 生成 3-(Benzyloxy)-6-bromo-2-methoxybenzoic acid
  参考文献：
  名称：

  Synthesis of 1,7-dimethoxy-2-hydroxyxanthone, a natural product with potential activity on erectile dysfunction

  摘要：

  The natural product, 1,7-dimethoxy-2-hydroxyxanthone (1), isolated from Securidaca inappendiculate Hassk, has a potential in the treatment of erectile dysfunction due to its significant relaxation activity on rabbit Corpus cavernosum. However, the isolation of compound 1 is problematic because of its high similarity in structure to its analogs. In this paper, the first synthesis of 1 was reported featuring two key reactions: a copper-catalyzed coupling reaction and an intramolecular cyclization. (C) 2013 De-Sheng Mei, Wen-Hu Duan. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.03.038
• 作为产物：
  描述：

  6-(benzyloxy)-2-formylphenyl ethyl carbonate 在 溴 、 potassium bromide 作用下， 以 水 为溶剂， 生成 6-(苄氧基)-3-溴-2-甲酰基苯基乙基碳酸酯
  参考文献：
  名称：

  Benzyne cyclization route to benzo[c]phenanthridine alkaloids. Synthesis of chelerythrine, decarine, and nitidine

  摘要：

  DOI：

  10.1021/jo00243a020

文献信息

• Benzyne cyclization route to benzo[c]phenanthridine alkaloids. Synthesis of chelerythrine, decarine, and nitidine
  作者：Satinder V. Kessar、Yash P. Gupta、Prasanna Balakrishnan、Kewal K. Sawal、Taj Mohammad、Mahesh Dutt

  DOI：10.1021/jo00243a020

  日期：1988.4
• Kessar, Satinder Vir; Gupta, Yash Pal; Mohammad, Taj, Heterocycles, 1984, vol. 22, # 12, p. 2723 - 2724
  作者：Kessar, Satinder Vir、Gupta, Yash Pal、Mohammad, Taj、Khurana, Achla、Sawal, Kewal Krishan

  DOI：——

  日期：——
• KESSAR, SATINDER V.;GUPTA, YASH P.;BALAKRISHNAN, PRASANNA;SAWAL, KEWAL K.+, J. ORG. CHEM., 53,(1988) N 8, 1708-1713
  作者：KESSAR, SATINDER V.、GUPTA, YASH P.、BALAKRISHNAN, PRASANNA、SAWAL, KEWAL K.+

  DOI：——

  日期：——
• Synthesis of 1,7-dimethoxy-2-hydroxyxanthone, a natural product with potential activity on erectile dysfunction
  作者：Wen-Jing Liu、De-Sheng Mei、Wen-Hu Duan

  DOI：10.1016/j.cclet.2013.03.038

  日期：2013.6

  The natural product, 1,7-dimethoxy-2-hydroxyxanthone (1), isolated from Securidaca inappendiculate Hassk, has a potential in the treatment of erectile dysfunction due to its significant relaxation activity on rabbit Corpus cavernosum. However, the isolation of compound 1 is problematic because of its high similarity in structure to its analogs. In this paper, the first synthesis of 1 was reported featuring two key reactions: a copper-catalyzed coupling reaction and an intramolecular cyclization. (C) 2013 De-Sheng Mei, Wen-Hu Duan. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.