4-甲基-4-羟基-6-环丙基-己-1-炔 | 100595-51-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-甲基-4-羟基-6-环丙基-己-1-炔
• 英文名称: 4-methyl-4-hydroxy-6-cyclopropyl-hex-1-yne
• 英文别名: 1-cyclopropyl-3-methylhex-5-yn-3-ol
• CAS: 100595-51-5
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: LEFXWSGHLDDUHA-UHFFFAOYSA-N

物化性质

• 沸点：
  248.3±13.0 °C(Predicted)
• 密度：
  0.984±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-甲基-4-羟基-6-环丙基-己-1-炔 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (+/-)-Methyl 7-<2β-(6-cyclopropyl-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：

  5-已烯-2-酮 在 diethylzinc 、 magnesium 、 mercury dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 37.08h， 生成 4-甲基-4-羟基-6-环丙基-己-1-炔
  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

• Omega cycloalkyl prostaglandins
  申请人：G. D. Searle & Co.

  公开号：US04713477A1

  公开（公告）日：1987-12-15

  This invention encompasses prostaglandins of the formula I ##STR1## wherein R represents hydrogen or lower alkyl containing 1 to 6 carbon atoms; X represents --CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C--, --CH.sub.2 --C.tbd.C--, --CH.sub.2 --CH.dbd.CH-- --CH.sub.2 --CH.sub.2 --CH.sub.2, --CH.dbd.CH--CH.sub.2 --, --C.tbd.C--CH.sub.2 --; and R.sub.1 represents cyclopropyl, cyclobutyl, cyclopentyl, 1-methylcyclopropyl or 1-methylcyclobutyl or XR.sub.1 together represent 1-methyl-1-cyclopropylethyl or 1-methyl-1-cyclobutylethyl; and R.sub.2 is lower alkyl having 1 to 4 carbon atoms or vinyl or ethynyl; the wavy line represents optional R or S sterochemistry These compounds are potent antisecretory agents.

  这项发明涵盖了公式I的前列腺素，其中R代表氢或含有1至6个碳原子的较低烷基；X代表--CH.sub.2 --，--CH.dbd.CH--，--C.tbd.C--，--CH.sub.2 --C.tbd.C--，--CH.sub.2 --CH.dbd.CH-- --CH.sub.2 --CH.sub.2 --CH.sub.2，--CH.dbd.CH--CH.sub.2 --，--C.tbd.C--CH.sub.2 --；和R.sub.1代表环丙基，环丁基，环戊基，1-甲基环丙基或1-甲基环丁基，或XR.sub.1一起表示1-甲基-1-环丙基乙基或1-甲基-1-环丁基乙基；而R.sub.2是具有1至4个碳原子的较低烷基，或乙烯或乙炔基；波浪线表示可选的R或S立体化学结构。这些化合物是有效的抗分泌剂。
• Omega-cycloalkyl prostaglandins
  申请人：G.D. Searle & Co.

  公开号：EP0142158A2

  公开（公告）日：1985-05-22

  This invention encompasses prostaglandins of the formula I wherein X represents cis or trans -CH=CH-, -C≡-, methylene or ethylene; R, represents a cycloalkyl group of the formula where m is 1 to 3 inclusive R2 represents hydrogen or lower alkyl with the proviso that the sum of the carbon atoms in X and R, is 7 or less. R' represents lower alkyl containing 1 to 6 carbon atoms, vinyl or ethynyl; wherein R''' represents hydroxymethyl, hydroxyacetyl or -CO2 R'''' wherein R"" represents hydrogen or lower alkyl containing 1 to 6 carbon atoms and the wavy line represents optional R or S stereochemistry.

  本发明包括式 I 的前列腺素 其中 X 代表顺式或反式-CH=CH-、-C≡-、亚甲基或亚乙基； R代表式中的环烷基 其中 m 为 1 至 3（包括 3 R2 代表氢或低级烷基，但 X 和 R 的碳原子之和必须为 7 或更少。 R' 代表含 1 至 6 个碳原子的低级烷基、乙烯基或乙炔基； 其中 R''' 代表羟甲基、羟基乙酰基或 -CO2 R'''' 其中 R""代表氢或含有 1 至 6 个碳原子的低级烷基，波浪线代表任选的 R 或 S 立体化学结构。
• COLLINS, PAUL W.;GASIECKI, ALAN F.
  作者：COLLINS, PAUL W.、GASIECKI, ALAN F.

  DOI：——

  日期：——
• COLLINS, PAUL W.;GASIECKI, ALAN F.;PERKINS, WILLIAM E.;GULLIKSON, GARY W.+, J. MED CHEM., 32,(1989) N, C. 1001-1006
  作者：COLLINS, PAUL W.、GASIECKI, ALAN F.、PERKINS, WILLIAM E.、GULLIKSON, GARY W.+

  DOI：——

  日期：——
• COLLINS, P. W.;GASIECKI, A. F.
  作者：COLLINS, P. W.、GASIECKI, A. F.

  DOI：——

  日期：——