N-p-Toluenesulfonyl-5-methyl-4-(1-allyl)-1-propenyl-2-oxazolidinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-p-Toluenesulfonyl-5-methyl-4-(1-allyl)-1-propenyl-2-oxazolidinone
• 英文别名: 4-hexa-2,5-dien-3-yl-5-methyl-3-(4-methylphenyl)sulfonyl-1,3-oxazolidin-2-one
• 化学式: C₁₇H₂₁NO₄S
• 分子量: 335.424
• InChiKey: NHVVQNOHBBZFQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1-methyl-2,3-pentadienyl tosylcarbamate 、 3-氯丙烯 在 二(氰基苯)二氯化钯 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 23.0h， 以79%的产率得到N-p-Toluenesulfonyl-5-methyl-4-(1-allyl)-1-propenyl-2-oxazolidinone
  参考文献：
  名称：

  Palladium-catalyzed regio- and stereoselective allylamination of allenic alcohols

  摘要：

  Palladium [PdCl2(PhCN)2 or Pd2(dba)3.CHCl3] catalyzes the reaction of O-(2,3-butadienyl) N-tosylcarbamates 1 with allylic chlorides to selectively provide trans-4,5-disubstituted oxazolidin-2-ones 2 in good yields. Under similar conditions, Pd(PPh3)4 catalyzes an N-allylation of 1 to give 3, and chloro-pi-allylpalladium(II) dimer promotes a dimerization of 1g and gives 4 as a major product together with 2.

  DOI：

  10.1021/jo00050a001

文献信息

• Palladium-catalyzed regio- and stereoselective allylamination of allenic alcohols
  作者：Masanari Kimura、Keigo Fugami、Shuji Tanaka、Yoshinao Tamaru

  DOI：10.1021/jo00050a001

  日期：1992.11

  Palladium [PdCl2(PhCN)2 or Pd2(dba)3.CHCl3] catalyzes the reaction of O-(2,3-butadienyl) N-tosylcarbamates 1 with allylic chlorides to selectively provide trans-4,5-disubstituted oxazolidin-2-ones 2 in good yields. Under similar conditions, Pd(PPh3)4 catalyzes an N-allylation of 1 to give 3, and chloro-pi-allylpalladium(II) dimer promotes a dimerization of 1g and gives 4 as a major product together with 2.
• Palladium-Catalyzed Stereoselective Allylaminocyclization and 1,3-Butadien-2-ylaminocyclization of Allenyl Tosylcarbamates
  作者：Masanari Kimura、Shuji Tanaka、Yoshinao Tamaru

  DOI：10.1021/jo00117a031

  日期：1995.6

  Palladium [PdCl2(PhCN)(2) or Pd-2(dba)(3) . CHCl3 (dba = dibenzylideneacetone)], in the presence of a base (Et(3)N or K2CO3) in THF at room temperature, catalyzes an allylaminocyclization of 2,3-butadienyl tosylcarbamates 1 with allylic chlorides to selectively provide trans-4,5-disubstituted 2-oxazolidinones 2 in good yields. Under similar conditions, Pd(PPh(3))(4) catalyzes an N-allylation of 1 to give 3. A limited number of 3,4-pentadienyl tosylcarbamates 5 undergo the allylaminocyclization to provide tetrahydro-1,3-oxazin-2-ones 6. In the absence of an allylic chloride, Pd(PPh(3))(4) and PdCl2(PhCN)(2) catalyze a formal dimerization of 1 to provide C-4-triene-substituted 2-oxazolidinones 4 in moderate to good yields.