allyl-2-d methanesulfonate | 307344-69-0

• 英文名称: allyl-2-d methanesulfonate
• CAS: 307344-69-0
• 化学式: C₄H₈O₃S
• 分子量: 137.164
• InChiKey: SUDMKGNNRMLBMF-WFVSFCRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.15
• 重原子数：
  8.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-硝基碘苯 、 allyl-2-d methanesulfonate 在 苯基氯化镁 、 copper(l) cyanide 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以50%的产率得到1-(allyl-2-d)-2-nitrobenzene
  参考文献：
  名称：

  Highly Stereoselective 7-Endo-Trig/Ring Contraction Cascade To Construct Pyrrolo[1,2-a]quinoline Derivatives

  摘要：

  With the cooperation of Cram's phenonium ion, a novel cascade reaction was illustrated to construct pyrrolo[1,2-a]quinolines as a sole diastereoisomer in good to excellent yields. Preliminary mechanistic studies revealed that the gamma-lactam ring and electron-rich arene are important driving forces for ring contraction.

  DOI：

  10.1021/ol100220c
• 作为产物：
  描述：

  <2-²H>-allyl alcohol 、 甲基磺酰氯 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 allyl-2-d methanesulfonate
  参考文献：
  名称：

  Cyclization of 1,6-Enynes Catalyzed by Gold Nanoparticles Supported on TiO₂: Significant Changes in Selectivity and Mechanism, as Compared to Homogeneous Au-Catalysis

  摘要：

  Gold nanoparticles supported on TiO2 (1.2 mol %) catalyze, for the first time under heterogeneous conditions, the cycloisomerization of a series of 1,6-enynes in high yields. In several cases, the product selectivity differs significantly as compared to homogeneous Au(I)-catalysis. Based on product analysis and stereoisotopic studies it is proposed that the major or exclusive pathway involves a 5-exo cyclization mode to form stereoselectively gold cyclopropyl carbenes that undergo a single cleavage pathway, in contrast to homogeneous Au-catalysis where the double cleavage pathway operates substantially.

  DOI：

  10.1021/ol301212j