(2S,3R,5S,7S)-2-hydroxy-3,5,7-trimethylcycloheptan-1-one | 808109-21-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,5S,7S)-2-hydroxy-3,5,7-trimethylcycloheptan-1-one
• CAS: 808109-21-9
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: TWDFAFITHMAHMF-KZVJFYERSA-N

物化性质

• 沸点：
  265.2±33.0 °C(Predicted)
• 密度：
  0.958±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3R,5S,7S)-2-hydroxy-3,5,7-trimethylcycloheptan-1-one 在 lead(IV) acetate 、 sodium tetrahydroborate 作用下， 以 甲醇 、 苯 为溶剂， 反应 2.17h， 生成 methyl (2S,4S,6R)-7-hydroxy-2,4,6-trimethylheptanoate
  参考文献：
  名称：

  Stereoselective hydrogenation of conjugate diene directed by hydroxy group and asymmetric synthesis of deoxypolypropionate units

  摘要：

  Optically active cyclic compounds carrying a conjugate diene and two hydroxy groups were prepared through the intramolecular Buchner reaction with a chiral tether and succeeding stereoselective conversion. Hydrogenation of the diene in the first step was not regio-selective but resulted in three regioisomeric monoenes. Nevertheless. the final saturated product carrying two stereogenic centers could be obtained in 98% stereochemical purity on further hydrogenation under optimized conditions. The high stereoselectivity throughout the multiple pathways is attributable to the effective direction by the hydroxy group. Ring cleavage of the produced stereochemically pure seven-membered ring compounds successfully resulted in synthetic intermediates for deoxypolypropionates. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.128
• 作为产物：
  描述：

  2,4,7,9-tetramethyl-8,9-dihydro-7H,11aH-6,10-dioxa-cycloheptacycloocten-11-one 在 镍 2,3,5-三甲基吡啶 、 lithium aluminium tetrahydride 、 氢气 、 对甲苯磺酸 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 52.42h， 生成 (2S,3R,5S,7S)-2-hydroxy-3,5,7-trimethylcycloheptan-1-one
  参考文献：
  名称：

  Asymmetric Synthesis of Deoxypolypropionate Units via Stereoselective Hydrogenation of Optically Active Cycloheptatriene

  摘要：

  Optically active polypropionate units were synthesized in 9-11 steps from 3,5-dimethylphenol. The sequence consists of the BUchner reaction controlled by a chiral 2,4-pentanediol tether and diastereoselective hydrogenation over Raney nickel.

  DOI：

  10.1021/ol0483596