2-(hydroxymethyl)brexane p-toluenesulfonate | 143545-81-7

• 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: 2-(hydroxymethyl)brexane p-toluenesulfonate
• 英文别名: [(1R,3R,6S,7S)-2-tricyclo[4.3.0.03,7]nonanyl]methyl 4-methylbenzenesulfonate
• CAS: 143545-81-7
• 化学式: C₁₇H₂₂O₃S
• 分子量: 306.426
• InChiKey: VUUXJZFMXZDPDO-CAOSSQGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(hydroxymethyl)brexane p-toluenesulfonate 在 sodium hydroxide 、 对甲苯磺酸 作用下， 以 水 为溶剂， 反应 27.0h， 生成 tricyclo<5.3.0.0^4,8>decan-2-ol
  参考文献：
  名称：

  Synthesis of brexan-2-one and ring-expanded congeners

  摘要：

  We report an efficient eight-step synthesis (26% overall yield) of brexan-2-one (tricyclo[4.3.0.0(3,7)]nonan-2-one, 12). This ketone then served as a convenient precursor to the mechanistically useful molecules, homobrexan-2-one (tricyclo[5.3.0.0(4,8)]decan-2-one, 14) and homobrexene (tricyclo[5.3.0.0(4,8)]dec-2-ene, 20). Several homologation sequences for the preparation of 14 were developed and can be easily adapted to allow selective introduction of C-13 and H-2 labels in 14 and 20 for various mechanistic studies.

  DOI：

  10.1021/jo00046a015
• 作为产物：
  描述：

  methyl brexane-2-carboxylate 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 30.0h， 生成 2-(hydroxymethyl)brexane p-toluenesulfonate
  参考文献：
  名称：

  Synthesis of brexan-2-one and ring-expanded congeners

  摘要：

  We report an efficient eight-step synthesis (26% overall yield) of brexan-2-one (tricyclo[4.3.0.0(3,7)]nonan-2-one, 12). This ketone then served as a convenient precursor to the mechanistically useful molecules, homobrexan-2-one (tricyclo[5.3.0.0(4,8)]decan-2-one, 14) and homobrexene (tricyclo[5.3.0.0(4,8)]dec-2-ene, 20). Several homologation sequences for the preparation of 14 were developed and can be easily adapted to allow selective introduction of C-13 and H-2 labels in 14 and 20 for various mechanistic studies.

  DOI：

  10.1021/jo00046a015

文献信息

• Synthesis of brexan-2-one and ring-expanded congeners
  作者：Alfred G. Stern、Alex Nickon

  DOI：10.1021/jo00046a015

  日期：1992.9

  We report an efficient eight-step synthesis (26% overall yield) of brexan-2-one (tricyclo[4.3.0.0(3,7)]nonan-2-one, 12). This ketone then served as a convenient precursor to the mechanistically useful molecules, homobrexan-2-one (tricyclo[5.3.0.0(4,8)]decan-2-one, 14) and homobrexene (tricyclo[5.3.0.0(4,8)]dec-2-ene, 20). Several homologation sequences for the preparation of 14 were developed and can be easily adapted to allow selective introduction of C-13 and H-2 labels in 14 and 20 for various mechanistic studies.