(1S,2S,4S)-1,2,7,7-tetramethylbicyclo[2.2.1]heptan-2-ol | 68330-44-9

• 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: (1S,2S,4S)-1,2,7,7-tetramethylbicyclo[2.2.1]heptan-2-ol
• 英文别名: (+)-2-methylisoborneol；(-)-S-methylisoborneol；2-methylisoborneol；(1S)-Exo-1,2,7,7-tetramethylbicyclo[2.2.1]heptan-2-OL
• CAS: 68330-44-9
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: LFYXNXGVLGKVCJ-LSJOCFKGSA-N

物化性质

• 熔点：
  167-168 °C
• 沸点：
  208.7±8.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,2S,4S)-1,2,7,7-tetramethylbicyclo[2.2.1]heptan-2-ol 、 乙腈 在 三氟化硼乙醚 作用下， 反应 24.0h， 以62%的产率得到exo-2-acetamido-4-methylbornane
  参考文献：
  名称：

  Welniak, Polish Journal of Chemistry, 2002, vol. 76, # 10, p. 1405 - 1411

  摘要：

  DOI：
• 作为产物：
  描述：

  左旋樟脑 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 18.0h， 生成 (1S,2S,4S)-1,2,7,7-tetramethylbicyclo[2.2.1]heptan-2-ol
  参考文献：
  名称：

  Synthesis of 2,2-disubstituted oxetanes from ketones with S-methyl-S-(sodiomethyl)-N-(4-tolylsulfonyl)sulfoximine

  摘要：

  DOI：

  10.1021/ja00340a019

文献信息

• Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C–O Bond Activation
  作者：Marc Magre、Eva Paffenholz、Bholanath Maity、Luigi Cavallo、Magnus Rueping

  DOI：10.1021/jacs.0c05917

  日期：2020.8.19

  A magnesium-catalyzed regiodivergent C–O bond cleavage protocol is presented. Readily available magnesium catalysts achieve the selective hydroboration of a wide range of epoxides and oxetanes yielding secondary and tertiary alcohols in excellent yields and regioselectivities. Experimental mechanistic investigations and DFT calculations provide insight into the unexpected regiodivergence and explain

  提出了镁催化的区域发散 C-O 键裂解方案。容易获得的镁催化剂实现了多种环氧化物和氧杂环丁烷的选择性硼氢化反应，以优异的产率和区域选择性得到仲醇和叔醇。实验机理研究和 DFT 计算提供了对意外区域发散的洞察，并解释了 C-O 键活化和产物形成的不同机制。
• Biosynthesis of the Off-Flavor 2-Methylisoborneol by the MyxobacteriumNannocystis exedens
  作者：Jeroen S. Dickschat、Thorben Nawrath、Verena Thiel、Brigitte Kunze、Rolf Müller、Stefan Schulz

  DOI：10.1002/anie.200702496

  日期：2007.11.5
• Synthesis of 1,4,7,7-tetramethylbicyclo[2.2.1]hept-exo-2-ylacylamines
  作者：N. G. Kozlov、L. A. Popova、V. A. Knizhnikov

  DOI：10.1007/bf00630598

  日期：1994.11
• Dehydration products of 2-methylisoborneol
  作者：R Schumann

  DOI：10.1016/s0043-1354(96)00330-2

  日期：1997.5

  7-Methylenebornane and 2-methyl-2-bornene have previously been identified as dehydration or degradation products of 2-methylisoborneol (MIB), a compound responsible for taste and odour problems in various water environments. Previously, the identification of these products has been based on mass spectral analysis only. The dehydration of MIB under a variety of conditions was reinvestigated and the products fully characterised by H-1 and C-13 n.m.r. and GC-MS. Comparison of EI mass spectra of the dehydration products of MIB with those published previously indicate that earlier assignments of MIB dehydration products are incorrect. (C) 1997 Elsevier Science Ltd.