3-[3,5-Dibromo-4-(3-bromo-propoxy)-phenyl]-2-oxo-propionic acid | 866456-14-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[3,5-Dibromo-4-(3-bromo-propoxy)-phenyl]-2-oxo-propionic acid
• 英文别名: 3-[3,5-Dibromo-4-(3-bromopropoxy)phenyl]-2-oxopropanoic acid；3-[3,5-dibromo-4-(3-bromopropoxy)phenyl]-2-oxopropanoic acid
• CAS: 866456-14-6
• 化学式: C₁₂H₁₁Br₃O₄
• 分子量: 458.929
• InChiKey: JJNFILGUMYPVFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[3,5-Dibromo-4-(3-bromo-propoxy)-phenyl]-2-oxo-propionic acid 在 sodium azide 、 盐酸羟胺 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 12.0h， 生成 3-[4-(3-Azido-propoxy)-3,5-dibromo-phenyl]-2-[(E)-hydroxyimino]-propionic acid
  参考文献：
  名称：

  An expeditious convergent synthesis of a dibromotyrosine alkaloid inhibitor of mycothiol-S-conjugate amidase

  摘要：

  A quick, economic synthesis of the alkaloid 1, an inhibitor of mycothiol-S-conjugate amidase (MCA) is reported. Starting from low-cost, commercially available 4-hydroxybenzaldehyde, the nine-step synthesis involved dibromination and coupling with N-acetylglycine to give a stable methyloxazole intermediate 5 which was hydrolyzed, oximated and coupled to agmatine to yield the oxime in -30% overall yield. It was not necessary to protect the oxime in the synthetic sequence thereby circumventing a deprotection step. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.109
• 作为产物：
  描述：

  3,5-二溴-4-羟基苯甲醛 在 盐酸 、 sodium acetate 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 乙酸酐 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 3-[3,5-Dibromo-4-(3-bromo-propoxy)-phenyl]-2-oxo-propionic acid
  参考文献：
  名称：

  An expeditious convergent synthesis of a dibromotyrosine alkaloid inhibitor of mycothiol-S-conjugate amidase

  摘要：

  A quick, economic synthesis of the alkaloid 1, an inhibitor of mycothiol-S-conjugate amidase (MCA) is reported. Starting from low-cost, commercially available 4-hydroxybenzaldehyde, the nine-step synthesis involved dibromination and coupling with N-acetylglycine to give a stable methyloxazole intermediate 5 which was hydrolyzed, oximated and coupled to agmatine to yield the oxime in -30% overall yield. It was not necessary to protect the oxime in the synthetic sequence thereby circumventing a deprotection step. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.109

文献信息

• An expeditious convergent synthesis of a dibromotyrosine alkaloid inhibitor of mycothiol-S-conjugate amidase
  作者：Bhanu M. Chanda、Rohidas S. Sulake

  DOI：10.1016/j.tetlet.2005.07.109

  日期：2005.9

  A quick, economic synthesis of the alkaloid 1, an inhibitor of mycothiol-S-conjugate amidase (MCA) is reported. Starting from low-cost, commercially available 4-hydroxybenzaldehyde, the nine-step synthesis involved dibromination and coupling with N-acetylglycine to give a stable methyloxazole intermediate 5 which was hydrolyzed, oximated and coupled to agmatine to yield the oxime in -30% overall yield. It was not necessary to protect the oxime in the synthetic sequence thereby circumventing a deprotection step. (c) 2005 Elsevier Ltd. All rights reserved.