[(1S,2S,3S,7S)-6-(benzenesulfonyl)-2-methyl-8-oxabicyclo[5.1.0]oct-5-en-3-yl]oxy-tert-butyl-dimethylsilane | 1171091-19-2

• 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: [(1S,2S,3S,7S)-6-(benzenesulfonyl)-2-methyl-8-oxabicyclo[5.1.0]oct-5-en-3-yl]oxy-tert-butyl-dimethylsilane
• CAS: 1171091-19-2
• 化学式: C₂₀H₃₀O₄SSi
• 分子量: 394.607
• InChiKey: BSAHXFQOEPOUJF-TWKWOARYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1S,2S,3S,7S)-6-(benzenesulfonyl)-2-methyl-8-oxabicyclo[5.1.0]oct-5-en-3-yl]oxy-tert-butyl-dimethylsilane 、 三甲基铝 在 dilithium tetrachlorocuprate 作用下， 以92%的产率得到(1S,4S,6S,7S)-3-(benzenesulfonyl)-6-[tert-butyl(dimethyl)silyl]oxy-4,7-dimethylcyclohept-2-en-1-ol
  参考文献：
  名称：

  Reagent-Directed Allylic Quadraselection. Chemoselective Anti- and Syn-Lawton S_N2′ Methylation of Seven-Membered Epoxyvinylsulfones

  摘要：

  Methods have been developed for regio- and stereoselective 1,4-syn or 1,4-anti methylation of seven-membered epoxyvinylsulfones. 1,4-Syn addition is achieved via the combination of Me2Zn and catalytic Li2CuCl4, a hitherto unexplored reagent combination. The complementary 1,4-anti addition relies on Cu(I) catalyzed methyl Grignard addition or (CH3)(3)Al assisted CH3Cu addition. The methods described were assayed on four diastereomeric stereodiads and on their parent epoxide.

  DOI：

  10.1021/ja9017557

文献信息

• SN2′ addition/1,2-elimination of dimethylsulfonium methylide with epoxy vinyl sulfones: synthesis of exocyclic cross-conjugated dienyl sulfones
  作者：Vikas Sikervar、Philip L. Fuchs

  DOI：10.1039/c0cc05405d

  日期：——

  Dimethylsulfonium methylide undergoes S(N)2' addition/1,2-elimination with epoxy vinyl sulfones to generate enantiopure six and seven membered cross-conjugated hydroxy vinyl sulfones. Moderate to excellent yields were obtained for both six and seven membered substrates.

  二甲基s亚甲基与环氧乙烯基砜进行S（N）2'加成/ 1,2-消除，生成对映体纯的六元和七元交叉共轭羟基乙烯基砜。对于六元和七元基板，均获得了中等至极好的产量。
• Reagent-Directed Allylic Quadraselection. Chemoselective <i>Anti</i>- and <i>Syn</i>-Lawton S_N2′ Methylation of Seven-Membered Epoxyvinylsulfones
  作者：Wan Pyo Hong、Ahmad El-Awa、Philip L. Fuchs

  DOI：10.1021/ja9017557

  日期：2009.7.8

  Methods have been developed for regio- and stereoselective 1,4-syn or 1,4-anti methylation of seven-membered epoxyvinylsulfones. 1,4-Syn addition is achieved via the combination of Me2Zn and catalytic Li2CuCl4, a hitherto unexplored reagent combination. The complementary 1,4-anti addition relies on Cu(I) catalyzed methyl Grignard addition or (CH3)(3)Al assisted CH3Cu addition. The methods described were assayed on four diastereomeric stereodiads and on their parent epoxide.