2-(3-hydroxypropyl)-4,4-dimethylcyclopent-2-en-1-one | 120584-80-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3-hydroxypropyl)-4,4-dimethylcyclopent-2-en-1-one
• 英文别名: 2-(3-hydroxypropyl)-4,4-dimethyl-2-cyclopentenone
• CAS: 120584-80-7
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: GFZWQZWHMXASSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(3-hydroxypropyl)-4,4-dimethylcyclopent-2-en-1-one 在 Amberlyst H₁₅ 正丁基锂 、 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 、 间氯过氧苯甲酸 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 丙酮 、 Petroleum ether 、 苯 为溶剂， 反应 183.25h， 生成 8-epi-9-epi-1-noralliacolide methyl ether
  参考文献：
  名称：

  Ladlow, Mark; Pattenden, Gerald, Journal of the Chemical Society. Perkin transactions I, 1988, p. 1107 - 1118

  摘要：

  DOI：
• 作为产物：
  描述：

  5-(tert-Butyl-diphenyl-silanyloxy)-pentanenitrile 在 磷酸 、 水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 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

文献信息

• LADLOW, MARK;PATTENDEN, GERALD, J. CHEM. SOC. PERKIN TRANS.,(1988) N 5, 1107-1118
  作者：LADLOW, MARK、PATTENDEN, GERALD

  DOI：——

  日期：——
• 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
  作者：Daisuke Wakasugi、Tsuyoshi Satoh

  DOI：10.1016/j.tet.2004.11.040

  日期：2005.1

  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.
• Ladlow, Mark; Pattenden, Gerald, Journal of the Chemical Society. Perkin transactions I, 1988, p. 1107 - 1118
  作者：Ladlow, Mark、Pattenden, Gerald

  DOI：——

  日期：——