2,2-difluoro-1-phthalimido-4-pentene | 110482-99-0

• 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: 2,2-difluoro-1-phthalimido-4-pentene
• 英文别名: 2,2-difluoropent-4-enyl phthalimide；2-(2,2-Difluoropent-4-enyl)isoindole-1,3-dione
• CAS: 110482-99-0
• 化学式: C₁₃H₁₁F₂NO₂
• 分子量: 251.233
• InChiKey: RJQLSYIQDCNFNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-difluoro-1-phthalimido-4-pentene 在 二甲基硫 、 臭氧 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 2,2-difluoro-1-phthalimido-5-hexyn-4-ol
  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：

  2,2-二氟-4-戊烯酸乙酯 在 吡啶 、 sodium tetrahydroborate 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.5h， 生成 2,2-difluoro-1-phthalimido-4-pentene
  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

• Synthesis of 5-amino- and 5-hydroxy-3,3-difluoropiperidines
  作者：Riccardo Surmont、Guido Verniest、Jan Willem Thuring、Peter ten Holte、Frederik Deroose、Norbert De Kimpe

  DOI：10.1039/c0ob00231c

  日期：——

  Synthetic routes toward new 5-amino- and 5-hydroxy-3,3-difluoropiperidines, which are of high interest as building blocks in medicinal chemistry, are described. The key step involves the N-halosuccinimide-induced cyclization of 2,2-difluoro-4-pentenylamines toward 5-halo-3,3-difluoropiperidines, which were used to synthesize 5-amino-3,3-difluoropiperidine. In a second strategy, iodolactonization of 2,2-difluoro-4-pentenoic acid gave the corresponding γ-lactone, which was transformed into 5-hydroxy-3,3-difluoropiperidine.

  本研究描述了新的 5-氨基和 5-羟基-3,3-二氟哌啶的合成路线，这些化合物是药物化学中备受关注的构建基块。关键步骤是通过 N-卤代丁二酰亚胺诱导 2,2-二氟-4-戊烯胺环化，生成 5-卤代-3,3-二氟哌啶，并用其合成 5-氨基-3,3-二氟哌啶。在第二种策略中，2,2-二氟-4-戊烯酸的碘内酯化反应产生了相应的γ-内酯，并将其转化为 5-羟基-3,3-二氟哌啶。
• Fluorinated diaminoalkyne derivatives
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US04707498A1

  公开（公告）日：1987-11-17

  Novel fluorinated diaminoalkyne derivatives are inhibitors of ornithine decarboxylase enzyme and have the following general Formula I: ##STR1## wherein R represents C.sub.1 -C.sub.4 alkyl, or preferably, hydrogen.

  新型氟代二氨基炔衍生物是鸟氨酸脱羧酶酶的抑制剂，其具有以下通式I：##STR1## 其中R代表C.sub.1-C.sub.4烷基，或更好地，氢。
• 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：——
• US4707498A
  申请人：——

  公开号：US4707498A

  公开（公告）日：1987-11-17