1-succinyl-(2,5-dimethoxy-3-bromo)aniline | 189579-19-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-succinyl-(2,5-dimethoxy-3-bromo)aniline
• 英文别名: 1-(3-bromo-2,5-dimethoxyphenyl)pyrrolidine-2,5-dione
• CAS: 189579-19-9
• 化学式: C₁₂H₁₂BrNO₄
• 分子量: 314.136
• InChiKey: CRIYUVJVQMCOJG-UHFFFAOYSA-N

物化性质

• 沸点：
  536.0±50.0 °C(Predicted)
• 密度：
  1.561±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-succinyl-(2,5-dimethoxy-3-bromo)aniline 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 1-{3-[(E)-(1R,2S,4S,5R,6S)-8-((2S,3S,6R)-3,6-Dimethoxy-3,6-dihydro-2H-pyran-2-yl)-1,5-dihydroxy-4-methoxy-2,6-dimethyl-non-7-enyl]-2,5-dimethoxy-phenyl}-pyrrolidine-2,5-dione
  参考文献：
  名称：

  Strategies for ansamycin antibiotics. asymmetric synthesis of the C(3)–C(21) subunit of herbimycin A

  摘要：

  The asymmetric synthesis of 25, which constitutes the C(3)-C(21) segment of the stereochemically complex ansa chain of herbimycin A (2) has been achieved. The approach features the furan-hydropyran transformations 7-->5 and 8-->6 and the fragment coupling of 5 and 6 to produce the trisubstituted alkene 4 with high stereoselectivity. Stereoselective addition of the aryl anion derived from 24, which possesses the novel BIPSOP protecting group for the primary amine function, to the lactol 22 then delivered 25 as the major product. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01163-6
• 作为产物：
  描述：

  3-溴-2,5-二甲氧基苯胺 在 乙酰氯 作用下， 以 苯 为溶剂， 反应 2.5h， 生成 1-succinyl-(2,5-dimethoxy-3-bromo)aniline
  参考文献：
  名称：

  Strategies for ansamycin antibiotics. asymmetric synthesis of the C(3)–C(21) subunit of herbimycin A

  摘要：

  The asymmetric synthesis of 25, which constitutes the C(3)-C(21) segment of the stereochemically complex ansa chain of herbimycin A (2) has been achieved. The approach features the furan-hydropyran transformations 7-->5 and 8-->6 and the fragment coupling of 5 and 6 to produce the trisubstituted alkene 4 with high stereoselectivity. Stereoselective addition of the aryl anion derived from 24, which possesses the novel BIPSOP protecting group for the primary amine function, to the lactol 22 then delivered 25 as the major product. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01163-6

文献信息

• Diprotection of primary amines as N-substituted-2,5-bis[(triisopropylsilyl)oxy]pyrroles (BIPSOP)
  作者：Stephen F. Martin、Chris Limberakis

  DOI：10.1016/s0040-4039(97)00443-7

  日期：1997.4

  Primary amines are diprotected as their 2,5-bis[(triisopropylsilyl)oxy]pyrrole derivatives (BIPSOP). This protecting group is stable to strong bases such as organolithiums and alkoxides at 0 °C and to temperatures up to about 150 °C. Removal may be accomplished by a mild two step sequence.

  伯胺以其2，5-双[（三异丙基甲硅烷基）氧基]吡咯衍生物（BIPSOP）进行双保护。该保护基团在0°C以及高达约150°C的温度下对强碱（如有机锂和醇盐）稳定。去除可以通过温和的两个步骤完成。