(R)-1-((1R,3S,5R)-6,6-Dimethyl-2-methylene-bicyclo[3.1.1]hept-3-yl)-ethanol | 137330-87-1

• 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: (R)-1-((1R,3S,5R)-6,6-Dimethyl-2-methylene-bicyclo[3.1.1]hept-3-yl)-ethanol
• 英文别名: (1R)-1-[(1R,3S,5R)-6,6-dimethyl-2-methylidene-3-bicyclo[3.1.1]heptanyl]ethanol
• CAS: 137330-87-1
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: BSPVWSPJSKKIPK-RCWTZXSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• 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

• 作为产物：
  描述：

  (-)-myrtenyl bromide 、 乙醛 在 氯化铵 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 以32%的产率得到(R)-1-((1R,3S,5R)-6,6-Dimethyl-2-methylene-bicyclo[3.1.1]hept-3-yl)-ethanol
  参考文献：
  名称：

  Diastereoselective route to enantiomerically pure homoallylic pinene alcohols from myrtenyl bromide and aldehydes

  摘要：

  With zinc dust in aq. NH4Cl/THF, mytenyl bromide (1) reacts with aldehydes (2) to give simple new pinene alcohols (beta-pinene-3-yl carbinols) (3), which are enantiomerically pure (100% de). The configuration of the new chiral centre at C-11 was determined by oxidation to the ketone 4 and stereoselective reduction to Cram alcohol 3.

  DOI：

  10.1016/s0957-4166(00)80458-9

文献信息

• Diastereoselective route to enantiomerically pure homoallylic pinene alcohols from myrtenyl bromide and aldehydes
  作者：Andreas Köver、Thilo Schottelius、H. Martin、R. Hoffmann

  DOI：10.1016/s0957-4166(00)80458-9

  日期：1991.1

  With zinc dust in aq. NH4Cl/THF, mytenyl bromide (1) reacts with aldehydes (2) to give simple new pinene alcohols (beta-pinene-3-yl carbinols) (3), which are enantiomerically pure (100% de). The configuration of the new chiral centre at C-11 was determined by oxidation to the ketone 4 and stereoselective reduction to Cram alcohol 3.
• Reactions of Myrtenylzinc Bromide with Carbonyl Compounds. Regio- and Diastereo-selectivity.
  作者：Inger Reidun Aukrust、Nils Olav Nilsen、Christian Rømming、Lars Skattebøl、Louisa Barré、Ole Hammerich、Inger Søtofte、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0385

  日期：——

  The organozinc reagent obtained from (-)-myrtenyl bromide and zinc powder in THF, under ultrasonic conditions, reacts rapidly with ketones and aldehydes furnishing homoallylic alcohols in high yields. The reactions were carried out both with preformed allylzinc compound and under Barbier conditions. Significant regio-and diastero-selectivity was observed; aldehydes gave preferentially products from a diastereoselective reaction at the most substituted carbon (gamma-allylation) of the allylzinc reagent, while ketones reacted at the least substituted carbon (alpha-allylation) and generally with less stereoselectivity. The absolute configuration of one of the alcohols was determined based on X-ray diffraction.