diethyl (1S,2R)-3-oxo-4-trimethylsilylcyclohex-4-ene-1,2-dicarboxylate | 75232-86-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diethyl (1S,2R)-3-oxo-4-trimethylsilylcyclohex-4-ene-1,2-dicarboxylate
• CAS: 75232-86-9
• 化学式: C₁₅H₂₄O₅Si
• 分子量: 312.438
• InChiKey: CSNFNNXOTYUKOV-CMPLNLGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-(trimethylsilyl)but-2-enoyl chloride 在 三乙胺 作用下， 以 甲苯 、 正戊烷 为溶剂， 反应 64.0h， 生成 diethyl (1S,2R)-3-oxo-4-trimethylsilylcyclohex-4-ene-1,2-dicarboxylate
  参考文献：
  名称：

  (Trimethylsilyl)vinylketene: a stable vinylketene and reactive enophile in [4 + 2] cycloadditions

  摘要：

  DOI：

  10.1021/jo01311a065

文献信息

• (Trialkylsilyl)vinylketenes:  Synthesis and Application as Diene Components in Diels−Alder Cycloadditions
  作者：Jennifer L. Loebach、Dawn M. Bennett、Rick L. Danheiser

  DOI：10.1021/jo981289u

  日期：1998.11.1

  New strategies for the synthesis of (trialkylsilyl)vinylketenes ("TAS-vinylketenes") are described based on the photochemical Wolff rearrangement of alpha-silyl-alpha'-diazo-alpha,beta-unsaturated ketones and the 4 pi electrocyclic ring opening of cyclobutenones. These remarkably robust vinylketenes undergo highly regioselective [4 + 2] cycloadditions with reactive olefinic and acetylenic dienophiles to produce highly substituted cyclohexenones and phenols in which the ketene carbonyl dominates in controlling the regiochemical course of the reaction. The stereochemical course of these cycloadditions follows the Alder endo rule, as illustrated in the reaction of nitropropene with TBS-vinylketene 22.
• DANHEISER R. L.; SARD H., J. ORG. CHEM., 1980, 45, NO 23, 4810-4812
  作者：DANHEISER R. L.、 SARD H.

  DOI：——

  日期：——