S-phenyl 2-methyl-3-oxo-3-phenylpropanethioate | 1052108-51-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: S-phenyl 2-methyl-3-oxo-3-phenylpropanethioate
• CAS: 1052108-51-6
• 化学式: C₁₆H₁₄O₂S
• 分子量: 270.352
• InChiKey: JWRXQTMEXZZTOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-羟基氨基甲酸叔丁酯 、 S-phenyl 2-methyl-3-oxo-3-phenylpropanethioate 在 2-乙基-2-唑啉 、 manganese(IV) oxide 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Catalytic Enantioselective O-Nitrosocarbonyl Aldol Reaction of β-Dicarbonyl Compounds

  摘要：

  The first example of a Cu-catalyzed asymmetric O-nitrosocarbonyl aldol reaction is described. This novel protocol allows convenient access to highly enantioenriched alpha-hydroxy-beta-ketoesters including the antibacterial natural. product kjellmanianone (up to 99% ee). MnO2 was introduced. as a:mild efficient oxidant for the in situ generation of nitrosocarbonyl species from hydroxamic acid derivatives.

  DOI：

  10.1021/ja309311z
• 作为产物：
  描述：

  苯甲酸 在 草酰氯 、 magnesium bromide diethyl etherate 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 S-phenyl 2-methyl-3-oxo-3-phenylpropanethioate
  参考文献：
  名称：

  软烯化法合成1,3-二酮和β-酮​​硫酯

  摘要：

  使用MgBr 2 ·OEt 2和i- Pr 2 NEt处理粗制酰氯后，酮和硫酯会进行软化和酰化反应，分别得到1,3-二酮和β-酮​​硫酯。粗制酰氯的使用避免了纯化和/或购买它们的需要，从而提高了效率并降低了成本。该方法以直接方式进行，不需要预先形成烯醇化物，从而进一步提高了其效率并使其非常容易进行。该方法适用于大规模应用。

  DOI：

  10.1021/acs.joc.9b00397

文献信息

• 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。
• 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.
• Synthesis of 1,3-Diketones and β-Keto Thioesters via Soft Enolization
  作者：Sabrina O. Aderibigbe、Don M. Coltart

  DOI：10.1021/acs.joc.9b00397

  日期：2019.8.2

  Ketones and thioesters undergo soft enolization and acylation using crude acid chlorides on treatment with MgBr2·OEt2 and i-Pr2NEt to give 1,3-diketones and β-keto thioesters, respectively. The use of crude acid chlorides adds efficiency and cost reduction by avoiding the need to purify and/or purchase them. The process is conducted in a direct fashion that does not require prior enolate formation

  使用MgBr 2 ·OEt 2和i- Pr 2 NEt处理粗制酰氯后，酮和硫酯会进行软化和酰化反应，分别得到1,3-二酮和β-酮​​硫酯。粗制酰氯的使用避免了纯化和/或购买它们的需要，从而提高了效率并降低了成本。该方法以直接方式进行，不需要预先形成烯醇化物，从而进一步提高了其效率并使其非常容易进行。该方法适用于大规模应用。
• Catalytic Enantioselective <i>O</i>-Nitrosocarbonyl Aldol Reaction of β-Dicarbonyl Compounds
  作者：Mahiuddin Baidya、Kimberly A. Griffin、Hisashi Yamamoto

  DOI：10.1021/ja309311z

  日期：2012.11.14

  The first example of a Cu-catalyzed asymmetric O-nitrosocarbonyl aldol reaction is described. This novel protocol allows convenient access to highly enantioenriched alpha-hydroxy-beta-ketoesters including the antibacterial natural. product kjellmanianone (up to 99% ee). MnO2 was introduced. as a:mild efficient oxidant for the in situ generation of nitrosocarbonyl species from hydroxamic acid derivatives.