3-[(2-ethoxy-2-oxoethyl)thio]cyclopentan-1-one

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-[(2-ethoxy-2-oxoethyl)thio]cyclopentan-1-one
• 英文别名: 3-((2-ethoxy-2-oxoethyl)thio)cyclopentan-1-one；Ethyl 2-(3-oxocyclopentyl)sulfanylacetate
• 化学式: C₉H₁₄O₃S
• 分子量: 202.274
• InChiKey: ULKNXIJKAWDUCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-环戊烯酮 、 巯基乙酸乙酯 在 四丁基氢氧化铵 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以242 mg的产率得到3-[(2-ethoxy-2-oxoethyl)thio]cyclopentan-1-one
  参考文献：
  名称：

  Selectivity Reversal during Thia-Michael Additions Using Tetrabutylammonium Hydroxide: Operationally Simple and Extremely High Turnover

  摘要：

  The use of tetrabutylammonium hydroxide as a novel and exceedingly efficient thia-Michael addition catalyst is herein described. This extremely simple methodology allows for the conjugate addition of a wide variety of mercaptan nucleophiles, and functions remarkably well with a very wide range of both classical and non-classical Michael acceptors. Contradistinctive to current literature reports, the use of this catalyst more efficiently promotes the addition of more basic thiols. This methodology is especially attractive and operationally simple, as it generally proceeds with only 1 mol% catalytic loading and without excess reagent, and the produced products typically require no purification.

  DOI：

  10.1055/s-0033-1341106

文献信息

• Selectivity Reversal during Thia-Michael Additions Using Tetrabutylammonium Hydroxide: Operationally Simple and Extremely High Turnover
  作者：Daniel Nicponski、Jennifer Marchi

  DOI：10.1055/s-0033-1341106

  日期：——

  The use of tetrabutylammonium hydroxide as a novel and exceedingly efficient thia-Michael addition catalyst is herein described. This extremely simple methodology allows for the conjugate addition of a wide variety of mercaptan nucleophiles, and functions remarkably well with a very wide range of both classical and non-classical Michael acceptors. Contradistinctive to current literature reports, the use of this catalyst more efficiently promotes the addition of more basic thiols. This methodology is especially attractive and operationally simple, as it generally proceeds with only 1 mol% catalytic loading and without excess reagent, and the produced products typically require no purification.