4-Cyclobutyl-3-buten-2-one | 98602-42-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Cyclobutyl-3-buten-2-one
• 英文别名: 4-cyclobutylbut-3-en-2-one
• CAS: 98602-42-7
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: WFGYHDUDDGCXIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914299000

反应信息

• 作为反应物：
  描述：

  4-Cyclobutyl-3-buten-2-one 在 palladium on activated charcoal 咪唑 、 氢气 、 magnesium 、 mercury dichloride 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、34.48 kPa 条件下， 反应 6.5h， 生成 (+/-)-Methyl 7-<2β-(6-cyclobutyl-4-hydroxy-4-methyl-1(E)-hexenyl)-3α-hydroxy-5-oxo-1α-cyclopentyl>-4(Z)-heptenoate
  参考文献：
  名称：

  18-Cycloalkyl analogs of enisoprost

  摘要：

  By use of standard cuprate methodology, a series of 18-cycloalkyl analogues of enisoprost was prepared in an effort to impede omega chain metabolism and prolong duration of gastric antisecretory activity. An initial product of omega chain oxidation, the C-20 hydroxy analogue, was also synthesized for pharmacological comparison. The cyclopropyl, cyclobutyl, and cyclopentyl analogues were approximately one-fourth as potent as enisoprost in inhibiting gastric acid secretion, while the cyclohexyl and cycloheptyl analogues showed very weak activity, and the 20-hydroxy compound was inactive at a dose 100 times the ED50 of enisoprost. The cyclobutyl compound had a longer duration of antisecretory action than enisoprost and the other cycloalkyl analogues. The cycloalkyl analogues unexpectedly possessed low diarrheogenic activity in rats.

  DOI：

  10.1021/jm00125a013
• 作为产物：
  描述：

  环丁基甲酰氯 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 苯 为溶剂， 25.0 ℃ 、34.48 kPa 条件下， 反应 11.5h， 生成 4-Cyclobutyl-3-buten-2-one
  参考文献：
  名称：

  18-Cycloalkyl analogs of enisoprost

  摘要：

  By use of standard cuprate methodology, a series of 18-cycloalkyl analogues of enisoprost was prepared in an effort to impede omega chain metabolism and prolong duration of gastric antisecretory activity. An initial product of omega chain oxidation, the C-20 hydroxy analogue, was also synthesized for pharmacological comparison. The cyclopropyl, cyclobutyl, and cyclopentyl analogues were approximately one-fourth as potent as enisoprost in inhibiting gastric acid secretion, while the cyclohexyl and cycloheptyl analogues showed very weak activity, and the 20-hydroxy compound was inactive at a dose 100 times the ED50 of enisoprost. The cyclobutyl compound had a longer duration of antisecretory action than enisoprost and the other cycloalkyl analogues. The cycloalkyl analogues unexpectedly possessed low diarrheogenic activity in rats.

  DOI：

  10.1021/jm00125a013

文献信息

• <scp>l</scp>-Proline-Catalyzed Direct Intermolecular Asymmetric Aldol Reactions of 1-Phenylthiocycloalkyl Carboxaldehydes with Ketones. Easy Access to Spiro- and Fused-Cyclobutyl Tetrahydrofurans and Cyclopentanones
  作者：Angela M. Bernard、Angelo Frongia、Regis Guillot、Pier P. Piras、Francesco Secci、Marco Spiga

  DOI：10.1021/ol063084a

  日期：2007.2.1

  [reaction: see text] Acid-catalyzed ring expansion of chiral cyclopropyl and cyclobutyl derivatives for the synthesis of carbo- and heterocyclic compounds is reported. The starting materials have been successfully prepared by l-proline-catalyzed direct asymmetric aldol reactions of 1-phenylthiocycloalkyl carboxaldehydes with ketones.

  [反应：见正文]据报道，用于合成碳-和杂环化合物的手性环丙基和环丁基衍生物的酸催化扩环反应。已经通过1-脯氨酸催化的1-苯基硫代环烷基羧醛与酮的直接不对称醛醇缩合反应成功地制备了起始原料。
• Omega cycloalkyl prostaglandins
  申请人：G. D. Searle & Co.

  公开号：US04499296A1

  公开（公告）日：1985-02-12

  This invention encompasses prostaglandins of the formula I ##STR1## wherein R'" represents hydroxymethyl, hydroxyacetyl or --CO.sub.2 R"" wherein R"" represents hydrogen or lower alkyl containing 1 to 6 carbon atoms; R' represents lower alkyl containing 1 to 6 carbon atoms, vinyl or ethynyl; R" represents cycloalkyl containing 3 to 5 carbon atoms; and the wavy line represents optional R,S stereochemistry. These compounds are potent antisecretory compounds and cytoprotective agents with reduced diarrhea side effects.

  该发明涵盖了公式I的前列腺素：##STR1## 其中R'"代表羟甲基、羟乙酰基或--CO.sub.2R""，其中R""表示氢或含有1至6个碳原子的低碳基；R'代表含有1至6个碳原子的低碳基、乙烯基或乙炔基；R"代表含有3至5个碳原子的环烷基；波浪线代表可选的R，S立体化学。这些化合物是具有降低腹泻副作用的强效抗分泌化合物和细胞保护剂。
• 18-Cycloalkyl analogs of enisoprost
  作者：Paul W. Collins、Alan F. Gasiecki、William E. Perkins、Gary W. Gullikson、Peter H. Jones、Raymond F. Bauer

  DOI：10.1021/jm00125a013

  日期：1989.5

  By use of standard cuprate methodology, a series of 18-cycloalkyl analogues of enisoprost was prepared in an effort to impede omega chain metabolism and prolong duration of gastric antisecretory activity. An initial product of omega chain oxidation, the C-20 hydroxy analogue, was also synthesized for pharmacological comparison. The cyclopropyl, cyclobutyl, and cyclopentyl analogues were approximately one-fourth as potent as enisoprost in inhibiting gastric acid secretion, while the cyclohexyl and cycloheptyl analogues showed very weak activity, and the 20-hydroxy compound was inactive at a dose 100 times the ED50 of enisoprost. The cyclobutyl compound had a longer duration of antisecretory action than enisoprost and the other cycloalkyl analogues. The cycloalkyl analogues unexpectedly possessed low diarrheogenic activity in rats.