(1R,2S,4R)-2-(2-hydroxyethyl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol | 162302-49-0

• 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,2S,4R)-2-(2-hydroxyethyl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
• 英文别名: (1R,2S)-2-(hydroxyethyl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 162302-49-0
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: NMKVYLJBDOVKTM-YUSALJHKSA-N

物化性质

• 沸点：
  283.5±8.0 °C(predicted)
• 密度：
  1.049±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S,4R)-2-(2-hydroxyethyl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 2-endo-Ethyl-bornanol-(2)
  参考文献：
  名称：

  Perry,M.; Maroni-Barnaud,Y., Bulletin de la Societe Chimique de France, 1969, p. 2372 - 2378

  摘要：

  DOI：
• 作为产物：
  描述：

  [(1R,2S,4R)-2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]acetic acid tert-butyl ester 在 lithium aluminium tetrahydride 作用下， 生成 (1R,2S,4R)-2-(2-hydroxyethyl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
  参考文献：
  名称：

  Camphor-derived amber/woody odorants: 1,7,7-trimethyl-2′-iso-propylspiro[bicyclo[2.2.1]heptane-2,4′-(1,3-dioxanes)]

  摘要：

  Six stereoisomers of a new camphor-derived 1,7,7-trimethyl-2'-iso-propylspiro[bicyclo[2.2.1]heptane-2,4'-(1,3-dioxane)] odorant were prepared. Their design with the help of an amber olfactophore model and structure-odour relationship are reported. The (IR,2S,4R,2'S) isomer has by far the strongest and the most characteristic amber-like odour. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00360-3

文献信息

• Synthesis of new optically active 1,3-diols with camphor and fenchone skeleton
  作者：Vladimir Dimitrov、Kalina Kostova、Manfred Hesse

  DOI：10.1016/s0957-4166(00)86259-x

  日期：1994.10

  The new optically active 1,3-diols 5–8 with (1R)-(+)-camphor and (1R)-(−)-fenchone skeleton were synthesized in high yields from the homoallylic alcohols 1–4 using a very effective ozonolysis followed by reduction. The absolute configuration of (1R, 2S, 12R)-6a was determined by a single crystal X-ray study.

  新的光学活性的1,3-二醇5-8用（1 - [R ）- （+） -樟脑和（1 - [R ）- （ - ） -葑酮骨架中从高烯丙基醇高收率合成1-4使用非常有效的臭氧分解，然后还原。通过单晶X射线研究确定（1 R，2 S，12 R）-6a的绝对构型。
• Camphor derivatives as new odorants
  申请人：GIVAUDAN-ROURE (INTERNATIONAL) S.A.

  公开号：EP0761664A1

  公开（公告）日：1997-03-12

  Compounds of the formula:    in which R1, R2 represent H or methyl and R3, R4 represent H, C1-4 alkyl or C2-4 alkenyl; R3 and R4 together can also be butylidene are interesting camphor derivatives. They exhibit valuable odour characteristics.

  如下式的化合物 其中 R1、R2 代表 H 或甲基，R3、R4 代表 H、C1-4 烷基或 C2-4 烯基；R3 和 R4 也可以是亚丁基。它们具有独特的气味特征。
• Preparation of Chiral Hydroxy Carbonyl Compounds and Diols by Ozonolysis of Olefinic Isoborneol and Fenchol Derivatives: Characterization of Stable Ozonides by1H-,13C-, and17O-NMR and Electrospray Ionization Mass Spectrometry
  作者：Kalina Kostova、Vladimir Dimitrov、Svetlana Simova、Manfred Hesse

  DOI：10.1002/(sici)1522-2675(19990908)82:9<1385::aid-hlca1385>3.0.co;2-y

  日期：1999.9.8

  The allylic and homoallylic alcohols 1-8, prepared from (+)-camphor and (-)-fenchone, were ozonized in Et2O at -78 and treated with Et3N or LiAlH4 to give the chiral hydroxy carbonyl compounds 9-16 and the diols 17-24, respectively (Scheme I). In the case of the diols 19 and WI the formation of new chiral centers proceeded with high diastereoselectivity. These diols were prepared highly diastereoselectively also by LiAlH4 reduction of the hydroxy carbonyl compounds 11 and 16a, respectively (Scheme 2). The absolute configuration of the new chiral centers in 19 and 24 was determined by X-ray and NMR methods. The ozonization of compounds 2, 3, 7, and 8 provided the relatively stable hydroxy-substituted 1,2,4-trioxolane derivatives (ozonides) 37-40 (Scheme 5) which were characterized by H-1- and C-13-NMR spectra. ESI-MS, and natural-abundance O-17-NMR spectra.