(S)-(+)-2-ethyl-2-(hydroxymethyl)cyclobutanone | 139166-96-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-(+)-2-ethyl-2-(hydroxymethyl)cyclobutanone
• 英文别名: (2S)-2-ethyl-2-(hydroxymethyl)cyclobutan-1-one
• CAS: 139166-96-4
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: CKUJXHBGQOYNDC-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  硅烷,(2-环亚丙基丁氧基)(1,1-二甲基乙基)二苯基- 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 四丁基氟化铵 、 D-(-)-酒石酸二异丙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.5h， 生成 (S)-(+)-2-ethyl-2-(hydroxymethyl)cyclobutanone
  参考文献：
  名称：

  A concise and enantioselective approach to cyclobutanones by tandem asymmetric epoxidation and enantiospecific ring expansion of cyclopropylidene alcohols. An enantiocontrolled synthesis of (+)- and (-)-.alpha.-cuparenones

  摘要：

  A tandem Katsuki-Sharpless asymmetric epoxidation and enantiospecific ring expansion of 2-alkyl(or 2-aryl)-2-cyclopropylideneethanols (1a-i) afforded chiral 1-alkyl(or 1-aryl)-1-(hydroxymethyl)cyclobutanones (3a-i) in high yields and high enantiomeric excess. These compounds are potentially valuable synthons for the enantioselective creation of the quaternary carbons. Hence, this enabled us to accomplish a concise and enantioselective total synthesis of both (+)- and (-)-alpha-cuparenones (11).

  DOI：

  10.1021/jo00032a021

文献信息

• A concise and enantioselective approach to cyclobutanones by tandem asymmetric epoxidation and enantiospecific ring expansion of cyclopropylidene alcohols. An enantiocontrolled synthesis of (+)- and (-)-.alpha.-cuparenones
  作者：Hideo Nemoto、Hiroki Ishibashi、Masatoshi Nagamochi、Keiichiro Fukumoto

  DOI：10.1021/jo00032a021

  日期：1992.3

  A tandem Katsuki-Sharpless asymmetric epoxidation and enantiospecific ring expansion of 2-alkyl(or 2-aryl)-2-cyclopropylideneethanols (1a-i) afforded chiral 1-alkyl(or 1-aryl)-1-(hydroxymethyl)cyclobutanones (3a-i) in high yields and high enantiomeric excess. These compounds are potentially valuable synthons for the enantioselective creation of the quaternary carbons. Hence, this enabled us to accomplish a concise and enantioselective total synthesis of both (+)- and (-)-alpha-cuparenones (11).