2-<4-<<(tert-Butyldimethylsilyl)oxy>methyl>phenyl>cyclohex-2-enone | 137273-40-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-<4-<<(tert-Butyldimethylsilyl)oxy>methyl>phenyl>cyclohex-2-enone
• 英文别名: 2-[4-[[Tert-butyl(dimethyl)silyl]oxymethyl]phenyl]cyclohex-2-en-1-one
• CAS: 137273-40-6
• 化学式: C₁₉H₂₈O₂Si
• 分子量: 316.516
• InChiKey: HCTGEGRLHILXRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.34
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲磺酸,三氟-,6-羰基-1-环己烯-1-基酯 、 <4-<<(tert-Butyldimethylsilyl)oxy>methyl>phenyl>tributyltin 在 tris-(dibenzylideneacetone)dipalladium(0) N-甲基吡咯烷酮 、 lithium chloride 作用下， 以83%的产率得到2-<4-<<(tert-Butyldimethylsilyl)oxy>methyl>phenyl>cyclohex-2-enone
  参考文献：
  名称：

  Catalyst tailoring for palladium-mediated cross coupling of arylstannanes with vinyl triflates

  摘要：

  Vinyl triflates couple smoothly with a variety of arylstannanes provided a polar, aprotic solvent is used in conjunction with a ''ligandless'' palladium catalyst, or a catalytic system involving weak ligands such as triphenylarsine. Commonly employed ligands, for example, triphenylphosphine, were found to strongly inhibit the coupling.

  DOI：

  10.1016/s0040-4039(00)92138-5

文献信息

• Palladium-catalyzed coupling of arylstannanes with organic sulfonates: a comprehensive study
  作者：Vittorio Farina、Bala Krishnan、Daniel R. Marshall、Gregory P. Roth

  DOI：10.1021/jo00072a028

  日期：1993.9

  The effect of ligands and lithium chloride on the rates of the palladium catalyzed coupling between organic triflates and arylstannanes was studied. The dependence of the rate on the ligand is similar to the one previously reported for the coupling of vinylstannanes, but in the present case triphenylarsine is shown to be superior to both triphenylphosphine and tri(2-furyl)phosphine. The effect of added chloride is complex and varies depending on solvent and ligand used. Ortho-substituted arylstannanes tend to transfer alkyl moieties to a substantial extent , and therefore rates and efficiencies of aryl vs alkyl transfer were quantitated. When ortho substituents that are potentially coordinating to tin are used, no rate acceleration in the alkyl transfer process was observed, which is in contrast with two recently reported studies that suggest nucleophilic assistance at tin to be important in the transmetalation step. An important side reaction in the coupling of poorly reactive vinyltriflates and most aryltriflates is the Pd-induced homocoupling of the stannane to form biaryls. The experimental factors that control this process were evaluated.