(1S,2R)-2-tritylcyclohexyl 6-methyl-2-methylenehept-5-enoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (1S,2R)-2-tritylcyclohexyl 6-methyl-2-methylenehept-5-enoate
• 英文别名: [(1S,2R)-2-tritylcyclohexyl] 6-methyl-2-methylidenehept-5-enoate
• 化学式: C₃₄H₃₈O₂
• 分子量: 478.675
• InChiKey: BADCTPBQYKFGPX-ACHIHNKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-tritylcyclohexyl 6-methyl-2-methylenehept-5-enoate 在 sodium permanganate 、 溶剂黄146 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 以73%的产率得到(1S,2R)-2-tritylcyclohexyl (2R,5S)-tetrahydro-2-(hydroxymethyl)-5-(2-hydroxy propan-2-yl)furan-2-carboxylate
  参考文献：
  名称：

  trans-2-Tritylcyclohexanol as a Chiral Auxiliary in Permanganate-Mediated Oxidative Cyclization of 2-Methylenehept-5-enoates: Application to the Synthesis of trans-(+)-Linalool Oxide

  摘要：

  The permanganate-mediated oxidative cyclization of a series of 2-methylenehept-5-eneoates bearing different chiral auxiliaries was investigated, leading to the discovery of trans-2-tritylcyclohexanol (TTC) as a highly effective chiral controller for the formation of the 2,5-substituted THF diol product with high diastereoselectivity (d(r) similar to 97:3). Chiral resolution of (+/-)-TTC, prepared in one step from cyclohexene oxide, afforded (-)-(1S,2R)-TTC (er >99:1), which was applied to the synthesis of (+)-trans-(2S,5S)-linalool oxide.

  DOI：

  10.1021/ol502454r
• 作为产物：
  描述：

  (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (1S,2R)-2-tritylcyclohexyl oxalate 在 4-二甲氨基吡啶 、 碘 、 magnesium 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 41.75h， 生成 (1S,2R)-2-tritylcyclohexyl 6-methyl-2-methylenehept-5-enoate
  参考文献：
  名称：

  trans-2-Tritylcyclohexanol as a Chiral Auxiliary in Permanganate-Mediated Oxidative Cyclization of 2-Methylenehept-5-enoates: Application to the Synthesis of trans-(+)-Linalool Oxide

  摘要：

  The permanganate-mediated oxidative cyclization of a series of 2-methylenehept-5-eneoates bearing different chiral auxiliaries was investigated, leading to the discovery of trans-2-tritylcyclohexanol (TTC) as a highly effective chiral controller for the formation of the 2,5-substituted THF diol product with high diastereoselectivity (d(r) similar to 97:3). Chiral resolution of (+/-)-TTC, prepared in one step from cyclohexene oxide, afforded (-)-(1S,2R)-TTC (er >99:1), which was applied to the synthesis of (+)-trans-(2S,5S)-linalool oxide.

  DOI：

  10.1021/ol502454r