3,3-difluoro-4-phthalimidobutanal | 110483-00-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3,3-difluoro-4-phthalimidobutanal
• 英文别名: 2,2-difluoro-1-phthalimidobutan-4-al；4-(1,3-dioxoisoindol-2-yl)-3,3-difluorobutanal
• CAS: 110483-00-6
• 化学式: C₁₂H₉F₂NO₃
• 分子量: 253.205
• InChiKey: VOWNDYCQODYVHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,3-difluoro-4-phthalimidobutanal 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 68.5h， 生成 2,2-difluoro-1,4-diphthalimido-5-hexyne
  参考文献：
  名称：

  2,2-Difluoro-5-hexyne-1,4-diamine. A potent enzyme-activated inhibitor of ornithine decarboxylase

  摘要：

  2,2-Difluoro-5-hexyne-1,4-diamine was prepared in an eight-step sequence from ethyl 2,2-difluoro-4-pentenoate and tested as an inhibitor of mammalian ornithine decarboxylase. It produces a time-dependent inhibition of the enzyme in vitro which shows saturation kinetics, with KI = 10 microM and tau 1/2 = 2.4 min. In rats, it produces a rapid, long-lasting, and dose-dependent decrease of ornithine decarboxylase activity in the ventral prostate, testis, and thymus. In contrast with the nonfluorinated analogue 5-hexyne-1,4-diamine (Danzin et al. Biochem. Pharmacol. 1983, 32, 941), 2,2-difluoro-5-hexyne-1,4-diamine is not a substrate of mitochondrial monoamine oxidase.

  DOI：

  10.1021/jm00121a031
• 作为产物：
  描述：

  2,2-difluoro-1-phthalimido-4-pentene 在 二甲基硫 、 臭氧 作用下， 生成 3,3-difluoro-4-phthalimidobutanal
  参考文献：
  名称：

  2,2-Difluoro-5-hexyne-1,4-diamine. A potent enzyme-activated inhibitor of ornithine decarboxylase

  摘要：

  2,2-Difluoro-5-hexyne-1,4-diamine was prepared in an eight-step sequence from ethyl 2,2-difluoro-4-pentenoate and tested as an inhibitor of mammalian ornithine decarboxylase. It produces a time-dependent inhibition of the enzyme in vitro which shows saturation kinetics, with KI = 10 microM and tau 1/2 = 2.4 min. In rats, it produces a rapid, long-lasting, and dose-dependent decrease of ornithine decarboxylase activity in the ventral prostate, testis, and thymus. In contrast with the nonfluorinated analogue 5-hexyne-1,4-diamine (Danzin et al. Biochem. Pharmacol. 1983, 32, 941), 2,2-difluoro-5-hexyne-1,4-diamine is not a substrate of mitochondrial monoamine oxidase.

  DOI：

  10.1021/jm00121a031

文献信息

• KENDRICK, DAVID A.;DANZIN, CHARLES;KOLB, MICHAEL, J. MED. CHEM., 32,(1989) N, C. 170-173
  作者：KENDRICK, DAVID A.、DANZIN, CHARLES、KOLB, MICHAEL

  DOI：——

  日期：——
• KOLB, MICHAEL;KENDRICK, DAVID A.
  作者：KOLB, MICHAEL、KENDRICK, DAVID A.

  DOI：——

  日期：——
• Fluorinated diaminoalkyne derivatives
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0229658B1

  公开（公告）日：1990-08-16
• US4707498A
  申请人：——

  公开号：US4707498A

  公开（公告）日：1987-11-17