(E)-3-(4-((tert-butyldimethylsilyl)oxy)but-2-enoyl)oxazolidin-2-one | 1197419-84-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (E)-3-(4-((tert-butyldimethylsilyl)oxy)but-2-enoyl)oxazolidin-2-one
• 英文别名: (E)-3-(4-(tert-butyldimethylsilyloxy)but-2-enoyl)oxazolidin-2-one；3-[(E)-4-[tert-butyl(dimethyl)silyl]oxybut-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 1197419-84-3
• 化学式: C₁₃H₂₃NO₄Si
• 分子量: 285.415
• InChiKey: WKVQQSWJVDISDE-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-((tert-butyldimethylsilyl)oxy)but-2-enoyl)oxazolidin-2-one 、 天然橡胶 在 copper(II) bis[bis((trifluoromethyl)sulfonyl)amide] 、 N,N'-(4R,4'R,5R,5'R)-2,2'-(propane-2,2-diyl)bis(5-methyl-4,5-dihydrooxazole-4,2-diyl)bis(methylene)dimethanesulfonamide 作用下， 以 硝基甲烷 为溶剂， 反应 66.0h， 以76%的产率得到3-((1S,6S)-6-((tert-butyldimethylsilyloxy)methyl)-4-methylcyclohex-3-enecarbonyl)oxazolidin-2-one
  参考文献：
  名称：

  Rational Design of Highly Effective Asymmetric Diels−Alder Catalysts Bearing 4,4′-Sulfonamidomethyl Groups

  摘要：

  The rational design of bis(oxazoline)-copper(II) catalysts based on postulated intramolecular secondary n-cation interaction for the highly enantioselective Diels-Alder reaction is presented. A theoretical calculation suggested that the n electrons of the 4,4'-sulfonamidomethyl groups successfully interact with the Cu(II) cation and that the counteranions with protons of sulfonamido groups. These secondary interactions might be essential for the high catalytic activity, the broad range of substrates, and the high level of induction of the enantioselectivity.

  DOI：

  10.1021/ja906098b
• 作为产物：
  描述：

  2-唑烷酮 、 (E)-4-((tert-butyldimethylsilyl)oxy)but-2-enoic acid 在 三甲基乙酰氯 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以36%的产率得到(E)-3-(4-((tert-butyldimethylsilyl)oxy)but-2-enoyl)oxazolidin-2-one
  参考文献：
  名称：

  Rational Design of Highly Effective Asymmetric Diels−Alder Catalysts Bearing 4,4′-Sulfonamidomethyl Groups

  摘要：

  The rational design of bis(oxazoline)-copper(II) catalysts based on postulated intramolecular secondary n-cation interaction for the highly enantioselective Diels-Alder reaction is presented. A theoretical calculation suggested that the n electrons of the 4,4'-sulfonamidomethyl groups successfully interact with the Cu(II) cation and that the counteranions with protons of sulfonamido groups. These secondary interactions might be essential for the high catalytic activity, the broad range of substrates, and the high level of induction of the enantioselectivity.

  DOI：

  10.1021/ja906098b

文献信息

• Site-specific introduction of gold-carbenoids by intermolecular oxidation of ynamides or ynol ethers
  作者：Paul W. Davies、Alex Cremonesi、Nicolas Martin

  DOI：10.1039/c0cc02736g

  日期：——

  Ynamides and ynol ethers undergo intermolecular gold-catalysed reaction with a nucleophilic oxidant to access metal-carbenoid reactivity patterns. A site-specific oxidation/1,2-insertion cascade is used for a general access to functionalised α,β-unsaturated carboxylic acid derivatives and vinylogous carbimates.

  Ynamides 和 ynol 乙醚通过金催化的分子间反应与亲核氧化剂发生反应，从而获得金-卡宾反应活性模式。采用特定位点的氧化/1,2-插入级联反应以通用方式合成功能化的 α,β-不饱和羧酸衍生物和延续酰胺。