cis-caran-trans-2-ol | 5561-13-7

• 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: cis-caran-trans-2-ol
• 英文别名: (-)-2-isocaranol；(1S,2R,3S)-caran-2-ol；(-)-cis-Caran-trans-(2)-ol ((-)-Isocaranol-(5))；(-)-cis-Caran-trans-(2)-ol；(-)-cis-Caran-trans-ol-(5)；(1S,2R,3S,6R)-3,7,7-trimethylbicyclo[4.1.0]heptan-2-ol
• CAS: 5561-13-7
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: RPPLFPVIBFQGJC-JQCXWYLXSA-N

物化性质

• 沸点：
  210.6±8.0 °C(Predicted)
• 密度：
  0.960±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 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：

  cis-caran-trans-2-ol 在 mercury(II) diacetate 作用下， 以 水 为溶剂， 反应 9.5h， 生成 (4S,6R)-4-(4-Chloro-phenyl)-2-oxy-6-((1S,2R,3S,6R)-3,7,7-trimethyl-bicyclo[4.1.0]hept-2-yloxy)-5,6-dihydro-4H-[1,2]oxazine-3-carbonitrile
  参考文献：
  名称：

  [4 + 2] Cycloadditions of Nitroalkenes in Water. Highly Asymmetric Synthesis of Functionalized Nitronates

  摘要：

  The [4 + 2] cycloadditions of (E)-2-aryl-1-cyano-1-nitroalkenes 1 with achiral and enantiopure vinyl ethers 2 and 3 carried out in sole water are reported. These reactions occur in a heterogeneous phase under mild conditions and are fast and highly stereoselective. By using(-)-N,N-dicyclohexyl-(1S)-isoborneol-10-sulfonamide as achiral auxiliary, the cycloadditions are totally asymmetric. The face selectivity is discussed in terms of the shape of the chiral auxiliary and the reactive conformation of vinyl ether.

  DOI：

  10.1021/jo010182v
• 作为产物：
  描述：

  (+)-trans-2-carene epoxide 生成 cis-caran-trans-2-ol
  参考文献：
  名称：

  Arbuzov,B.A. et al., Doklady Chemistry, 1971, vol. 199, p. 690 - 692

  摘要：

  DOI：

文献信息

• Molecular addition compounds. 14. Convenient preparations of representative dialkylborane reagents using the new, highly reactive N-ethyl-N-isopropylaninine-borane reagent (BACH-EI™)
  作者：Herbert C. Brown、Josyula V.B. Kanth、Marek Zaidlewicz

  DOI：10.1016/s0040-4020(99)00272-0

  日期：1999.5

  Convenient procedures for the preparation of representative dialkylborane reagents, diisopinocampheylborane, [1S]-2-diisocaranylborane, 9-borabicyclo[3,3,1]nonane, dicyclohexylborane and disiamylborane, using the new, highly reactive N-ethyl-N-isopropylaniline-borane reagent (BACH-EI™) in dioxane and tetrahydrofuran are described.

  使用新的高反应性N-乙基-N-异丙基苯胺-描述了在二恶烷和四氢呋喃中的硼烷试剂（BACH-EI™）。
• Free-Radical Hydroxylation Reactions of Alkylboronates
  作者：Christine Cadot、Peter I. Dalko、Janine Cossy、Cyril Ollivier、Rachel Chuard、Philippe Renaud

  DOI：10.1021/jo0201833

  日期：2002.10.1

  to give alkoxyamines. Reduction of the alkoxyamines with zinc in acetic acid affords the desired alcohols. The whole procedure is particularly mild and does not require any basic condition. The two approaches presented in this paper are valuable and represent mild alternatives to the classical alkaline oxidation of organoboranes to alcohols.

  已经研究了通过烯烃的氢硼化容易制备的B-烷基儿茶酚硼烷的自由基羟基化。当使用分子氧作为氧化剂时，无需碱处理即可直接获得相应的醇。路易斯碱添加剂（例如Et3N或DABCO）的存在对选择性和收率产生有益影响。或者，2,2,6,6-四甲基哌啶-N-氧基（TEMPO）与B-烷基儿茶酚硼烷清洁反应，得到可以被第二当量的TEMPO捕获的烷基自由基，得到烷氧基胺。用锌在乙酸中还原烷氧基胺，得到所需的醇。整个过程特别温和，不需要任何基本条件。
• The chemistry of terpenes. Part V. The preparation of some stereoisomeric caranamines and a study of their conformations
  作者：W. Cocker、A. C. Pratt、P. V. R. Shannon

  DOI：10.1039/j39680000484

  日期：——

  Preparative routes to the previously unknown (–)-cis-caran-trans-2-amine, (+)-cis-caran-cis-4-amine, (–)-cis-caran-trans-4-amine, (+)-cis-caran-cis-5-amine, and (–)-cis-caran-trans-5-amine are described, and their configurations are established. The (+)-caranamine prepared by Baeyer and by Menon and Simonsen is probably the enantiomorph of (–)-trans-caran-cis-2-amine now described. The probable conformations

  制备至先前未知的（–）-顺式-caran-反式-2-胺，（+）-顺式-caran-顺式-4-胺，（–）-顺式-caran-反式-4-胺，（+描述了）-顺式-caran-顺式-5-胺和（-）-顺式-caran-反式-5-胺，并确定了它们的构型。的（+） -由拜尔和梅农和西蒙森制备caranamine可能的对映体（ - ） -反式-caran-顺-2-胺说明。这些化合物的可能构象是根据其nmr光谱中的α-质子带宽来讨论的。
• The chemistry of terpenes. Part IX. Deamination of the caranamines
  作者：W. Cocker、D. P. Hanna、P. V. R. Shannon

  DOI：10.1039/j39690001302

  日期：——

  spectroscopic techniques. The 2- and the 5-amines yielded products expected from the appropriate cyclopropyl-stabilised carbonium ion, whilst the 4-amines afforded a more complex range of products, including the new compounds, R(–)-trans-3-(1-hydroxyethyl)-6,6-dimethylbicyclo[3,1,0]hexane and (+)-3β,7,7-trimethyl-anti-cis-anti-tricyclo[4,1,0,02.4]heptane.

  （ - ） -的脱氨基产物反式-caran-顺-2-胺，（ - ） -顺式-caran-反式-2-胺，（ - ） -顺式-caran-反式-4-胺，（+） -顺-caran-顺-4-胺，（ - ） -顺式-caran-反式-5-胺，和（+） -顺式-caran-顺-5-胺已经被分离，并且其特征在于，采用色谱，化学和光谱技术。2-胺和5-胺生成的产物可从适当的环丙基稳定的碳酸根离子获得，而4-胺提供的产物范围更复杂，包括新化合物R（–）-反式-3-（1-羟乙基）-6,6-二甲基双环[3,1,0]己烷和（+）-3β，7,7-三甲基-反-顺-反-三环[4， 1,0,0 2.4 ]庚烷。
• The chemistry of terpenes. Part III. Oxidative hydroboronation of car-2-, -3-, and -4-enes
  作者：W. Cocker、P. V. R. Shannon、P. A. Staniland

  DOI：10.1039/j39670000485

  日期：——

  The products of oxidative hydroboronation of car-2-, -3-, and -4-enes have been investigated and their configurations established.

  已经研究了car-2-，-3-和-4-烯的氧化氢硼化产物，并确定了它们的构型。