S-phenyl 5-methylhex-4-enethioate | 104322-69-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: S-phenyl 5-methylhex-4-enethioate
• 英文别名: S-Phenyl 5-methylhex-4-enethioate
• CAS: 104322-69-2
• 化学式: C₁₃H₁₆OS
• 分子量: 220.335
• InChiKey: CPRAAUOUVXITSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-benzyloxy-[(4S)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetaldehyde 、 S-phenyl 5-methylhex-4-enethioate 在 二异丙胺 、 B-(trifluoromethanesulfonyloxy)-9-borabicyclo[3.3.1]nonane 作用下， 以 乙醚 为溶剂， 以79%的产率得到(2R)-S-phenyl 2-((1R,2R)-2-(benzyloxy)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-1-hydroxyethyl)-5-methylhex-4-enethioate
  参考文献：
  名称：

  Total synthesis of (+)-pseudomonic acid C

  摘要：

  DOI：

  10.1021/jo00370a040
• 作为产物：
  描述：

  5-甲基-4-己烯酸 、 苯硫酚 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以86%的产率得到S-phenyl 5-methylhex-4-enethioate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/ol801498u

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.
• Total synthesis of (+)-pseudomonic acid C
  作者：D. R. Williams、J. L. Moore、M. Yamada

  DOI：10.1021/jo00370a040

  日期：1986.10