(2S)-ethyl 2-[(2-dimethylaminomethyl-3-oxospiro[3.5]non-1-en-1-yl)amino]-3-{4-[(3,5-dichloroisonicotinoyl)amino]phenyl}propionate | 571153-41-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-ethyl 2-[(2-dimethylaminomethyl-3-oxospiro[3.5]non-1-en-1-yl)amino]-3-{4-[(3,5-dichloroisonicotinoyl)amino]phenyl}propionate
• 英文别名: ethyl (2S)-3-[4-[(3,5-dichloropyridine-4-carbonyl)amino]phenyl]-2-[[2-[(dimethylamino)methyl]-3-oxospiro[3.5]non-1-en-1-yl]amino]propanoate
• CAS: 571153-41-8
• 化学式: C₂₉H₃₄Cl₂N₄O₄
• 分子量: 573.519
• InChiKey: HRQJKVGPSAFZQL-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S)-ethyl 2-[(2-dimethylaminomethyl-3-oxospiro[3.5]non-1-en-1-yl)amino]-3-{4-[(3,5-dichloroisonicotinoyl)amino]phenyl}propionate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (S)-3-{4-[(3,5-Dichloro-pyridine-4-carbonyl)-amino]-phenyl}-2-(2-dimethylaminomethyl-3-oxo-spiro[3.5]non-1-en-1-ylamino)-propionic acid
  参考文献：
  名称：

  Efficient Synthesis of 3-Aminocyclobut-2-en-1-ones:  Squaramide Surrogates as Potent VLA-4 Antagonists

  摘要：

  [GRAPHICS]A novel series of uniquely functionalized 3-aminocyclobut-2-en-1-ones has been prepared by facile condensation of a variety of cyclobuta-1,3-diones with a phenylalanine-derived primary amine. These systems subsequently lend themselves to substitution at C-2 by reaction with a variety of electrophilic reagents including N-halosuccinimides, sulfenyl chlorides, and Eschenmoser's salt. Compounds from this novel series are potent antagonists of VLA-4.

  DOI：

  10.1021/ol034701n
• 作为产物：
  描述：

  3-乙氧基螺[3.5]-2-壬烯-1-酮 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 72.0h， 生成 (2S)-ethyl 2-[(2-dimethylaminomethyl-3-oxospiro[3.5]non-1-en-1-yl)amino]-3-{4-[(3,5-dichloroisonicotinoyl)amino]phenyl}propionate
  参考文献：
  名称：

  Efficient Synthesis of 3-Aminocyclobut-2-en-1-ones:  Squaramide Surrogates as Potent VLA-4 Antagonists

  摘要：

  [GRAPHICS]A novel series of uniquely functionalized 3-aminocyclobut-2-en-1-ones has been prepared by facile condensation of a variety of cyclobuta-1,3-diones with a phenylalanine-derived primary amine. These systems subsequently lend themselves to substitution at C-2 by reaction with a variety of electrophilic reagents including N-halosuccinimides, sulfenyl chlorides, and Eschenmoser's salt. Compounds from this novel series are potent antagonists of VLA-4.

  DOI：

  10.1021/ol034701n

文献信息

• Efficient Synthesis of 3-Aminocyclobut-2-en-1-ones:  Squaramide Surrogates as Potent VLA-4 Antagonists
  作者：Stephen Brand、Benjamin C. de Candole、Julien A. Brown

  DOI：10.1021/ol034701n

  日期：2003.6.1

  [GRAPHICS]A novel series of uniquely functionalized 3-aminocyclobut-2-en-1-ones has been prepared by facile condensation of a variety of cyclobuta-1,3-diones with a phenylalanine-derived primary amine. These systems subsequently lend themselves to substitution at C-2 by reaction with a variety of electrophilic reagents including N-halosuccinimides, sulfenyl chlorides, and Eschenmoser's salt. Compounds from this novel series are potent antagonists of VLA-4.