1-((1S,2S)-1-(4-(p-methylbenzenesulfonyloxy)butyl)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-methylenecyclohexyl)ethan-1-one | 1256293-31-8

• 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: 1-((1S,2S)-1-(4-(p-methylbenzenesulfonyloxy)butyl)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-methylenecyclohexyl)ethan-1-one
• CAS: 1256293-31-8
• 化学式: C₂₅H₃₆O₆S
• 分子量: 464.623
• InChiKey: WQQUMQHWWAOUOS-GIFXNVAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-((1S,2S)-1-(4-(p-methylbenzenesulfonyloxy)butyl)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-methylenecyclohexyl)ethan-1-one 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以91%的产率得到1-((1S,2S)-1-(4-azidobutyl)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-methylenecyclohexyl)ethan-1-one
  参考文献：
  名称：

  Synthesis of a Functionalized 7,6-Bicyclic Spiroimine Ring Fragment of the Spirolides

  摘要：

  The asymmetric synthesis of a functionalized 7,6-spiroimine related to the spirolides is described. Intermolecular Diels-Alder cycloaddition of a chiral trisubstituted dienophile and Danishefsky's diene enabled simultaneous installation of the C7 and C29 stereocenters. Further transformations and late-stage aza-Wittig cyclization afforded the spiroimine in good yield. During this study, an unprecedented 14-membered dialdimine was also obtained.

  DOI：

  10.1021/ol102525w
• 作为产物：
  描述：

  1-[(1S,2S)-1-(4-hydroxybutyl)-2-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methylidenecyclohexyl]ethan-1-one 、 对甲苯磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到1-((1S,2S)-1-(4-(p-methylbenzenesulfonyloxy)butyl)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-methylenecyclohexyl)ethan-1-one
  参考文献：
  名称：

  Synthesis of a Functionalized 7,6-Bicyclic Spiroimine Ring Fragment of the Spirolides

  摘要：

  The asymmetric synthesis of a functionalized 7,6-spiroimine related to the spirolides is described. Intermolecular Diels-Alder cycloaddition of a chiral trisubstituted dienophile and Danishefsky's diene enabled simultaneous installation of the C7 and C29 stereocenters. Further transformations and late-stage aza-Wittig cyclization afforded the spiroimine in good yield. During this study, an unprecedented 14-membered dialdimine was also obtained.

  DOI：

  10.1021/ol102525w