2-amino-3-[3-(tert-butyldiphenylsilanyloxy)propyl]-5,5-dimethylcyclopenta-1,3-diene-1-carbonitrile | 845895-07-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-amino-3-[3-(tert-butyldiphenylsilanyloxy)propyl]-5,5-dimethylcyclopenta-1,3-diene-1-carbonitrile
• 英文别名: 2-amino-3-[3-[tert-butyl(diphenyl)silyl]oxypropyl]-5,5-dimethylcyclopenta-1,3-diene-1-carbonitrile
• CAS: 845895-07-0
• 化学式: C₂₇H₃₄N₂OSi
• 分子量: 430.665
• InChiKey: NFYBWDGWEBLALF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  59.04
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-amino-3-[3-(tert-butyldiphenylsilanyloxy)propyl]-5,5-dimethylcyclopenta-1,3-diene-1-carbonitrile 在 磷酸 、 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.67h， 生成 2-(3-hydroxypropyl)-4,4-dimethylcyclopent-2-en-1-one
  参考文献：
  名称：

  A novel synthesis, including asymmetric synthesis, of 2,4,4-trisubstituted 2-cyclopentenones based on the reaction of 1-chlorovinyl p-tolyl sulfoxides with acetonitrile and its homologues

  摘要：

  Reaction of 1-chlorovinyl p-tolyl sulfoxides, which were synthesized from chloromethyl p-tolyl sulfoxide and ketones in high overall yields, with cyanomethyllithium (lithium alpha-carbanion of acetonitrile) gave adducts in high to quantitative yields. The adducts were treated with LDA followed by lithium alpha-carbanion of the homologues of acetonitrile to give 3,5,5-trisubstituted enaminonitriles in good to high yields. Hydrolysis of the enaminonitriles under acidic conditions gave 2,4,4-trisubstituted 2-cyclopentenones in good yields. By using the optically active chloromethyl p-tolyl sulfoxide and unsymmetrical ketones, this procedure gave the optically pure 2,4,4-trisubstituted 2-cyclopentenones. The scope and limitations of this method and the mechanism of the reactions are also discussed. These procedures offer a new and effective method for the synthesis of 2,4,4-trisubstituted 2-cyclopentenones from four components, ketones, chloromethyl p-tolyl sulfoxide, acetonitrile, and its homologues. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.040
• 作为产物：
  描述：

  4-chloro-3,3-dimethyl-4-(p-tolylsulfinyl)butanenitrile 、 5-(tert-Butyl-diphenyl-silanyloxy)-pentanenitrile 在 lithium diisopropyl amide 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以99%的产率得到2-amino-3-[3-(tert-butyldiphenylsilanyloxy)propyl]-5,5-dimethylcyclopenta-1,3-diene-1-carbonitrile
  参考文献：
  名称：

  A novel synthesis, including asymmetric synthesis, of 2,4,4-trisubstituted 2-cyclopentenones based on the reaction of 1-chlorovinyl p-tolyl sulfoxides with acetonitrile and its homologues

  摘要：

  Reaction of 1-chlorovinyl p-tolyl sulfoxides, which were synthesized from chloromethyl p-tolyl sulfoxide and ketones in high overall yields, with cyanomethyllithium (lithium alpha-carbanion of acetonitrile) gave adducts in high to quantitative yields. The adducts were treated with LDA followed by lithium alpha-carbanion of the homologues of acetonitrile to give 3,5,5-trisubstituted enaminonitriles in good to high yields. Hydrolysis of the enaminonitriles under acidic conditions gave 2,4,4-trisubstituted 2-cyclopentenones in good yields. By using the optically active chloromethyl p-tolyl sulfoxide and unsymmetrical ketones, this procedure gave the optically pure 2,4,4-trisubstituted 2-cyclopentenones. The scope and limitations of this method and the mechanism of the reactions are also discussed. These procedures offer a new and effective method for the synthesis of 2,4,4-trisubstituted 2-cyclopentenones from four components, ketones, chloromethyl p-tolyl sulfoxide, acetonitrile, and its homologues. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.040