(1R,2R,3S,5S)-3-[(4-methoxyphenyl)methyl]-6,6-dimethylbicyclo[3.1.1]heptan-2-ol | 188851-34-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2R,3S,5S)-3-[(4-methoxyphenyl)methyl]-6,6-dimethylbicyclo[3.1.1]heptan-2-ol
• CAS: 188851-34-5
• 化学式: C₁₇H₂₄O₂
• 分子量: 260.376
• InChiKey: XAKRMBKSEFFDRH-BFJAYTPKSA-N

物化性质

• 沸点：
  373.2±15.0 °C(Predicted)
• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,5S)-3-[(4-methoxyphenyl)methyl]-6,6-dimethylbicyclo[3.1.1]heptan-2-ol 在 sodium tetrahydroborate 、 manganese(ll) chloride 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 2.17h， 生成 [(1R,2R,3S,5S)-3-[(4-methoxyphenyl)methyl]-6,6-dimethyl-2-bicyclo[3.1.1]heptanyl] (3S)-3-hydroxybutanoate
  参考文献：
  名称：

  The Use of Chiral Auxiliaries Prepared from (-)-β-Pinene in Stereoselective Reduction of β-Ketobutyrates

  摘要：

  Chiral auxiliaries previously prepared from (-)-beta-pinene (3), alcohols 5a-e and 6, were transformed into beta-ketobutyrates 7a-e and 8 respectively. These compounds were stereoselectively reduced by NaBH4 in the presence of additives (MnCl2 or CaCl2), leading to the corresponding beta-hydroxy butyrates 10a-e and 11 in good chemical yield and poor to moderate stereoselectivities (de 0%-60%). The configuration at the newly generated stereogenic center in 10a was determined to be S through its transformation into S-(+)-butanediol.

  DOI：

  10.1080/00397910008087342
• 作为产物：
  描述：

  (1R)-(+)-诺蒎酮 在 palladium on activated charcoal 氢氧化钾 、 lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 24.5h， 生成 (1R,2R,3S,5S)-3-[(4-methoxyphenyl)methyl]-6,6-dimethylbicyclo[3.1.1]heptan-2-ol
  参考文献：
  名称：

  Synthesis and structural determination of new chiral auxiliaries derived from (−)-β-pinene

  摘要：

  New chiral auxiliaries, alcohols syn-11a,e and syn-12a,e, were readily synthesized in a stereoselective manner from (-)-beta-pinene. Their stereochemical determinations have been made on the basis of nOe experiments. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00523-x