Methyl 2-[3-oxo-3-phenylsulfanyl-2-[(2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)methyl]propanoyl]benzoate | 1052108-60-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2-[3-oxo-3-phenylsulfanyl-2-[(2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)methyl]propanoyl]benzoate
• 英文别名: methyl 2-[3-oxo-3-phenylsulfanyl-2-[(2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)methyl]propanoyl]benzoate
• CAS: 1052108-60-7
• 化学式: C₂₅H₂₈O₆S
• 分子量: 456.56
• InChiKey: RMLBGAAPGZFBID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  S-phenyl 3-(2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)propanethioate 、 硫基丙酸苯酯 在 magnesium bromide diethyl etherate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以80%的产率得到Methyl 2-[3-oxo-3-phenylsulfanyl-2-[(2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)methyl]propanoyl]benzoate
  参考文献：
  名称：

  A Practical Synthesis of β-Keto Thioesters by Direct Crossed-Claisen Coupling of Thioesters and N-Acylbenzotriazoles

  摘要：

  在MgBr2·OEt2和i-Pr2NEt处理下，硫酯通过化学选择性软烯醇化和N-酰基苯并三氮唑酰化，生成β-酮硫酯。无需先形成烯醇盐，反应在未经处理的二氯甲烷中进行，且对空气开放。

  DOI：

  10.1055/s-0029-1216971

文献信息

• Direct Carbon−Carbon Bond Formation via Chemoselective Soft Enolization of Thioesters: A Remarkably Simple and Versatile Crossed-Claisen Reaction Applied to the Synthesis of LY294002
  作者：Guoqiang Zhou、Daniel Lim、Don M. Coltart

  DOI：10.1021/ol801498u

  日期：2008.9.1

  Thioesters undergo chemoselective soft enolization and acylation by N-acylbenzotriazoles on treatment with MgBr(2)center dot OEt(2) and i-Pr(2)NEt to give beta-keto thioesters. Prior enolate formation is not required, and the reaction is conducted using untreated CH(2)Cl(2) open to the air. The coupled products are stable synthetic equivalents of beta-keto acids and can be converted directly into beta-keto esters, beta-keto amides, and beta-diketones under mild conditions. The utility of this carbon-carbon bond-forming method is shown through the synthesis of the PI3-K inhibitor LY294002.
• A Practical Synthesis of β-Keto Thioesters by Direct Crossed-Claisen Coupling of Thioesters and N-Acylbenzotriazoles
  作者：Don Coltart、Guoqiang Zhou、Daniel Lim、Fang Fang

  DOI：10.1055/s-0029-1216971

  日期：2009.10

  Thioesters undergo chemoselective soft enolization and acylation with N-acylbenzotriazoles on treatment with MgBr2˙OEt2 and i-Pr2NEt to give β-keto thioesters. Prior enolate formation is not required and the reaction is conducted using untreated dichloromethane open to the air.

  在MgBr2·OEt2和i-Pr2NEt处理下，硫酯通过化学选择性软烯醇化和N-酰基苯并三氮唑酰化，生成β-酮硫酯。无需先形成烯醇盐，反应在未经处理的二氯甲烷中进行，且对空气开放。