(1R,2S)-2-ethenyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol | 130979-66-7

• 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)-2-ethenyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
• 英文别名: (1R,2S,4R)-2-ethenyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol；endo-2-vinylborneol；2-endo-Vinyl-bornanol-(2)
• CAS: 130979-66-7
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: GCIUUXWWELOLLP-YUSALJHKSA-N

物化性质

• 沸点：
  50 °C(Press: 0.05 Torr)
• 密度：
  1.032±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (1R,2S)-2-ethenyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 为溶剂， 生成 2-endo-Ethyl-bornanol-(2)
  参考文献：
  名称：

  Capmau,M.-L. et al., Bulletin de la Societe Chimique de France, 1968, p. 3233 - 3238

  摘要：

  DOI：
• 作为产物：
  描述：

  methylenedimethyl sulfurane 、 白樟油 以 四氢呋喃 为溶剂， 以60%的产率得到(1R,2S)-2-ethenyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
  参考文献：
  名称：

  一种使用二甲基甲磺酸甲酯合成同系的烯丙基醇的新方法

  摘要：

  过量的二甲基亚砜甲基化物与各种脂族和芳族酮的反应仅以良好的收率产生均聚的烯丙基醇。

  DOI：

  10.1016/s0040-4039(00)73035-8

文献信息

• Thermal Isomerization of Isoborneols and Dehydroisoborneols to New Chiral Building Blocks in Terpenoid Synthesis
  作者：Georg Rüedi、Hans-Jürgen Hansen

  DOI：10.1002/hlca.200490179

  日期：2004.8

  readily prepared in excellent yields from (+)-camphor and (+)-5,6-dehydrocamphor (2) by aryl, vinyl, or alkyl Grignard addition in the presence of stoichiometric amounts of CeCl3, were thermally isomerized in a flow reactor system under DGPTI (dynamic gas-phase thermo-isomerization) conditions at temperatures between 480 and 630° to give the enantiomerically pure monocyclic carbonyl compounds 7a–7d, 19a

  取代的异冰片醇1a - 1g和5,6-脱氢异冰片醇6a - 6c易于制备，可以通过（+）-樟脑和（+）-5,6-脱氢樟脑（2）的芳基，乙烯基或烷基格氏试剂的加成而制得。在流式反应器系统中，在DGPTI（动态气相热异构化）条件下，在480至630°的温度下，将化学计量的CeCl 3的存在进行热异构化，从而得到对映体纯的单环羰基化合物7a - 7d，19a，  b，23和24。在所有情况下，产物的形成都在高度区域性和立体选择性方面进行。新的立体发生中心的绝对构型由1 H-NOE测量确定。提出芳基底物1a - 1d的DGPTI可以在双自由基中间状态形成后进行分子中最弱的单键的初始裂解，随后进行分子内H-抽象以提供苯乙酮衍生物7a - 7d。2 H标记研究进一步支持了该反应路径，该研究表明OH基是唯一的H源。相反，允许乙烯基基材1e和6b的DGPTI一致。Retro -ene和oxy-应对重排。在5
• Synthesis of New Tricyclic Phosphines and Phosphinites by Intramolecular Diels−Alder Reactions of Trivalent Phospholes
  作者：E. Mattmann、F. Mercier、L. Ricard、F. Mathey

  DOI：10.1021/jo025713+

  日期：2002.7.1

  Phospholes bearing an allyl-X substituent at phosphorus tend to undergo an intramolecular Diels-Alder cycloaddition (IMDA) leading to the corresponding tricyclic derivative. When X = O or NR, the IMDA easily takes place at room temperature. When X = CH2, the IMDA slowly takes place around 110-140 degrees C, as a function to the substitution pattern of the dienic system. Two tricyclic derivatives (X

  在磷上带有烯丙基-X取代基的磷脂易于发生分子内Diels-Alder环加成反应（IMDA），从而生成相应的三环衍生物。当X = O或NR时，IMDA很容易在室温下发生。当X = CH2时，IMDA缓慢地在110-140摄氏度左右发生，这是二烯体系取代模式的函数。通过对P-硫化物的X射线晶体结构分析，已表征了两个三环衍生物（X = O和 ）。
• Synthesis and absolute configuration of new chiral epoxyalcohols by stereoselective epoxidation of allylic and homoallylic alcohols with a (1R)-(+)-camphor skeleton
  作者：Vladimir Dimitrov、Irena Philipova、Svetlana Simova

  DOI：10.1016/0957-4166(96)00168-1

  日期：1996.5

  100% diastereoselectively to 10. The epoxyalcohol 10 underwent a stereoselective intramolecular cyclisation during the epoxydation with rearrangement of the camphor skeleton to the oxatricyclo derivative 11. The absolute configurations of the new chiral compounds were determined by NMR methods.

  VO（acac）2 /叔丁基氢过氧化物体系将手性非外消旋醇1-5立体选择性环氧化。由醇1-4生成的环氧醇6-9可以高收率合成，所得非对映异构体经色谱分离为纯净形式。均丙醇5将100％非对映选择性地环氧化为10。环氧醇10在环氧化过程中经历了立体选择性的分子内环化作用，其中樟脑骨架重排为氧三环衍生物11。通过NMR方法确定了新的手性化合物的绝对构型。
• 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.
• Anhydrous cerium(III) chloride — Effect of the drying process on activity and efficiency
  作者：Vladimir Dimitrov、Kalina Kostova、Miroslav Genov

  DOI：10.1016/s0040-4039(96)01479-7

  日期：1996.9

  The activity and efficiency of anhydrous CeCl3 depend strongly on the drying procedure. Deactivation of CeCl3 occurs during the drying process as a result of hydrolysis by the hydrate water, when heating above 90 degrees C. The highly active CeCl3, prepared by an improved drying procedure, is demonstrated to activate rapidly (in catalytic and stoichiometric amounts) ketones at room temperature, providing excellent addition of organometallic reagents. Copyright (C) 1996 Elsevier Science Ltd