2-[[(4R)-4-[(4-bromophenyl)methyl]-1-(3,5-dichlorophenyl)-4-methyl-5-oxoimidazolidin-2-ylidene]amino]acetic acid | 397329-91-8

• 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: 2-[[(4R)-4-[(4-bromophenyl)methyl]-1-(3,5-dichlorophenyl)-4-methyl-5-oxoimidazolidin-2-ylidene]amino]acetic acid
• CAS: 397329-91-8
• 化学式: C₁₉H₁₆BrCl₂N₃O₃
• 分子量: 485.164
• InChiKey: XYUCSXDEBIXSQO-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  82
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[[(4R)-4-[(4-bromophenyl)methyl]-1-(3,5-dichlorophenyl)-4-methyl-5-oxoimidazolidin-2-ylidene]amino]acetic acid 在 草酰氯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 3-(4-bromobenzyl)-1-(3,5-dichlorophenyl)-3-methyl-1,6-dehydroimidazo[1,2-a]imidazole-2,5-dione
  参考文献：
  名称：

  Regiocontrolled synthesis of highly-functionalized fused imidazoles: a novel synthesis of second generation LFA-1 inhibitors

  摘要：

  A new and reliable route to a new class of LFA-1 inhibitors such as (2) has been developed. A key aspect of this route is the transformation of amino amide 5 into iodide 3 in four steps. Iodide 3 is a key advanced intermediate used in the synthesis of all second-generation 1H-imidazo[1,2-alpha]imidazol-2-one LFA-1 inhibitors. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01535-1
• 作为产物：
  描述：

  (2R)-2-amino-3-(4-bromophenyl)-N-(3,5-dichlorophenyl)-2-methyl-propionamide 在 lithium hydroxide 、 三苯基膦 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 三乙胺 为溶剂， 反应 15.5h， 生成 2-[[(4R)-4-[(4-bromophenyl)methyl]-1-(3,5-dichlorophenyl)-4-methyl-5-oxoimidazolidin-2-ylidene]amino]acetic acid
  参考文献：
  名称：

  Regiocontrolled synthesis of highly-functionalized fused imidazoles: a novel synthesis of second generation LFA-1 inhibitors

  摘要：

  A new and reliable route to a new class of LFA-1 inhibitors such as (2) has been developed. A key aspect of this route is the transformation of amino amide 5 into iodide 3 in four steps. Iodide 3 is a key advanced intermediate used in the synthesis of all second-generation 1H-imidazo[1,2-alpha]imidazol-2-one LFA-1 inhibitors. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01535-1