2,2-dimethylcyclopentanenitrile | 153580-00-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,2-dimethylcyclopentanenitrile
• 英文别名: 2,2-Dimethylcyclopentane-1-carbonitrile
• CAS: 153580-00-8
• 化学式: C₈H₁₃N
• 分子量: 123.198
• InChiKey: YFQUNIXBJWWKJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  190.4±9.0 °C(Predicted)
• 密度：
  0.89±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2-dimethylcyclopentanenitrile 在 氢氧化钾 、 sodium tetrahydroborate 、 臭氧 、 乙酰氯 、 lithium diisopropyl amide 作用下， 生成 6,6-dimethyl-2-oxaspiro<4.4>nonan-1-one
  参考文献：
  名称：

  .alpha.-Spirocyclopentyl- and .alpha.-spirocyclopropyl-.gamma.-butyrolactones: conformationally constrained derivatives of anticonvulsant and convulsant .alpha.,.alpha.-disubstituted .gamma.-butyrolactones

  摘要：

  To further study the putative gamma-butyrolactone site of the GABA(A)/chloride channel complex, constrained derivatives of convulsant and anticonvulsant alpha,alpha-disubstituted gamma-butyrolactones (alpha-spirocyclopropyl- and alpha-spirocyclopentyl-gamma-butyrolactones) were synthesized and evaluated biologically. Most of the spirocyclopropyl agents were anticonvulsants when tested against pentylenetetrazole-induced seizures in mice. These agents effectively displaced (35)[S]-tert-butylbicyclophosphorothionate ((35)[S] -TBPS), a ligand for the picrotoxin binding site of the GABA(A)/chloride channel, from rat neuronal membranes and affected the GABA-mediated current in hippocampal neurons. The monomethyl-substituted spirocyclopropyl agent with a methyl group cis to the carbonyl (15) potentiates GABA-induced current whereas the trans derivative (16) blocks the current. The only anticonvulsant in the spirocyclopentyl series was the unsubstituted spirocyclopentyl compound 2. All the other substituted spirocyclopentyl targets were inactive in vivo at the highest dose tested except for convulsant 9, which has a trans 2,5-dimethyl-substituted cyclopentyl ring. All the spirocyclopentyl derivatives displaced (35)[S]-TBPS from rat neuronal membranes very effectively, and they also all potentiated GABA-induced chloride current except for convulsant 9 which blocked the current. From the data obtained in this investigation, it appears that when the volume occupied above and below the lactone ring is as large as that occupied by spirocyclopentyl agent 9, convulsant activity is observed. Groups with less volume in these areas either are inactive in the behavioral test or have anticonvulsant activity. When bound to the GABA(A)/chloride channel, the larger molecules may stabilize the closed state of the channel whereas the smaller molecules may stabilize the open state.

  DOI：

  10.1021/jm00028a011
• 作为产物：
  描述：

  2,2-二甲基环戊酮 、 对甲基苯磺酰甲基异腈 在 potassium tert-butylate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 以50%的产率得到2,2-dimethylcyclopentanenitrile
  参考文献：
  名称：

  .alpha.-Spirocyclopentyl- and .alpha.-spirocyclopropyl-.gamma.-butyrolactones: conformationally constrained derivatives of anticonvulsant and convulsant .alpha.,.alpha.-disubstituted .gamma.-butyrolactones

  摘要：

  To further study the putative gamma-butyrolactone site of the GABA(A)/chloride channel complex, constrained derivatives of convulsant and anticonvulsant alpha,alpha-disubstituted gamma-butyrolactones (alpha-spirocyclopropyl- and alpha-spirocyclopentyl-gamma-butyrolactones) were synthesized and evaluated biologically. Most of the spirocyclopropyl agents were anticonvulsants when tested against pentylenetetrazole-induced seizures in mice. These agents effectively displaced (35)[S]-tert-butylbicyclophosphorothionate ((35)[S] -TBPS), a ligand for the picrotoxin binding site of the GABA(A)/chloride channel, from rat neuronal membranes and affected the GABA-mediated current in hippocampal neurons. The monomethyl-substituted spirocyclopropyl agent with a methyl group cis to the carbonyl (15) potentiates GABA-induced current whereas the trans derivative (16) blocks the current. The only anticonvulsant in the spirocyclopentyl series was the unsubstituted spirocyclopentyl compound 2. All the other substituted spirocyclopentyl targets were inactive in vivo at the highest dose tested except for convulsant 9, which has a trans 2,5-dimethyl-substituted cyclopentyl ring. All the spirocyclopentyl derivatives displaced (35)[S]-TBPS from rat neuronal membranes very effectively, and they also all potentiated GABA-induced chloride current except for convulsant 9 which blocked the current. From the data obtained in this investigation, it appears that when the volume occupied above and below the lactone ring is as large as that occupied by spirocyclopentyl agent 9, convulsant activity is observed. Groups with less volume in these areas either are inactive in the behavioral test or have anticonvulsant activity. When bound to the GABA(A)/chloride channel, the larger molecules may stabilize the closed state of the channel whereas the smaller molecules may stabilize the open state.

  DOI：

  10.1021/jm00028a011

文献信息

• Benzoic acid derivatives and related compounds as antiarrhythmic agents
  申请人：——

  公开号：US20020137968A1

  公开（公告）日：2002-09-26

  Benzoic acid derivatives of the formula I 1 where X is oxygen, sulfur, —NH, —NR 1 , —N—CN, —N—OR 1 or —N—NO 2 ; Y is a single bond, —C═C—, or —NH; R 1 is alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocyclo, or (heterocyclo)alkyl; and R 2 is aryl or heterocyclo. The compounds of formula I are useful in the treatment of arrhythmia.

  公式I的苯甲酸衍生物 其中X为氧、硫、—NH、—NR 1 、—N—CN、—N—OR 1 或—N—NO 2 ； Y为单键、—C═C—或—NH； R 1 为烷基、烯基、炔基、芳基、环烷基、杂环烷基或(杂环烷基)；和 R 2 为芳基或杂环烷基。公式I的化合物在心律失常的治疗中很有用。
• US6624309B1
  申请人：——

  公开号：US6624309B1

  公开（公告）日：2003-09-23
• .alpha.-Spirocyclopentyl- and .alpha.-spirocyclopropyl-.gamma.-butyrolactones: conformationally constrained derivatives of anticonvulsant and convulsant .alpha.,.alpha.-disubstituted .gamma.-butyrolactones
  作者：Eileen M. Peterson、Kun Xu、Katherine D. Holland、Ann C. McKeon、Steven M. Rothman、James A. Ferrendelli、Douglas F. Covey

  DOI：10.1021/jm00028a011

  日期：1994.1

  To further study the putative gamma-butyrolactone site of the GABA(A)/chloride channel complex, constrained derivatives of convulsant and anticonvulsant alpha,alpha-disubstituted gamma-butyrolactones (alpha-spirocyclopropyl- and alpha-spirocyclopentyl-gamma-butyrolactones) were synthesized and evaluated biologically. Most of the spirocyclopropyl agents were anticonvulsants when tested against pentylenetetrazole-induced seizures in mice. These agents effectively displaced (35)[S]-tert-butylbicyclophosphorothionate ((35)[S] -TBPS), a ligand for the picrotoxin binding site of the GABA(A)/chloride channel, from rat neuronal membranes and affected the GABA-mediated current in hippocampal neurons. The monomethyl-substituted spirocyclopropyl agent with a methyl group cis to the carbonyl (15) potentiates GABA-induced current whereas the trans derivative (16) blocks the current. The only anticonvulsant in the spirocyclopentyl series was the unsubstituted spirocyclopentyl compound 2. All the other substituted spirocyclopentyl targets were inactive in vivo at the highest dose tested except for convulsant 9, which has a trans 2,5-dimethyl-substituted cyclopentyl ring. All the spirocyclopentyl derivatives displaced (35)[S]-TBPS from rat neuronal membranes very effectively, and they also all potentiated GABA-induced chloride current except for convulsant 9 which blocked the current. From the data obtained in this investigation, it appears that when the volume occupied above and below the lactone ring is as large as that occupied by spirocyclopentyl agent 9, convulsant activity is observed. Groups with less volume in these areas either are inactive in the behavioral test or have anticonvulsant activity. When bound to the GABA(A)/chloride channel, the larger molecules may stabilize the closed state of the channel whereas the smaller molecules may stabilize the open state.