(1R,4R)-(+)-4-methyl-2-cyclohexen-1-ol | 152442-06-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,4R)-(+)-4-methyl-2-cyclohexen-1-ol
• 英文别名: (1R,4R)-4-methylcyclohex-2-en-1-ol
• CAS: 152442-06-3
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: YOQLXQKRNWMILQ-BQBZGAKWSA-N

物化性质

• 沸点：
  171.6±19.0 °C(Predicted)
• 密度：
  0.960±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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,4R)-(+)-4-methyl-2-cyclohexen-1-ol 生成 3,4-dimethylcyclohexane
  参考文献：
  名称：

  CONSIGLIO G.; MORANDINI F.; PICCOLO O., J. AMER. CHEM. SOC., 1981 103 NO 7, 1846-1847

  摘要：

  DOI：
• 作为产物：
  描述：

  diethyl [(3R,6R)-3-hydroxy-6-methylcyclohexen-1-yl] phosphate 生成 (1R,4R)-(+)-4-methyl-2-cyclohexen-1-ol
  参考文献：
  名称：

  WENDER P. A.; ERHARDT J. M.; LETENDRE L. J., J. AMER. CHEM. SOC., 1981, 103, NO 8, 2114-2116

  摘要：

  DOI：

文献信息

• Enantioselective opening of cyclic vinyl epoxides with organoaluminium reagents catalysed by copper salts
  作者：Olivier Equey、Alexandre Alexakis

  DOI：10.1016/j.tetasy.2004.04.011

  日期：2004.5

  enantioselective conjugate addition of trialkylaluminium reagents to cyclic vinyl epoxides catalysed by copper salts and chiral phosphorus-based ligands. The reaction must be carried out in THF, otherwise we observed only oligomeric products. The best ees have been obtained with CuTC as the copper salt and a 2,2′-binaphthyl-based phosphorus ligand. Both opening products (SN2 and SN2′ pathways) were

  在本文中，我们报道了将三烷基铝试剂对映选择性共轭加成到由铜盐和手性磷基配体催化的环状乙烯基环氧化物中的条件。该反应必须在THF中进行，否则我们只能观察到低聚产物。最好EES已经获得CUTC作为铜盐和2,2- '联萘基磷配位体。两种开放产物（S N 2和S N 2 '途径）均具有良好的对映选择性和中等至良好的区域选择性。
• A Multigram, Catalytic and Enantioselective Synthesis of Optically Active 4-Methyl-2-cyclohexen-1-one: a Useful Chiral Building Block
  作者：Fabio Bertozzi、Paolo Crotti、Ben L. Feringa、Franco Macchia、Mauro Pineschi

  DOI：10.1055/s-2001-11445

  日期：——

  The first catalytic asymmetric synthesis of both (R)-(+)- and (S)-(-)-4-methyl-2-cyclohexen-1-one and a new and improved synthesis of both enantiomers of (1S,4S)-(-) and (1R,4R)-(+)-4-methyl-2-cyclohexen-1-ol was developed on a multigram scale. The key step of this approach is the asymmetric catalyzed addition of Me2Zn (SN2'-pathway) to racemic 1,3-cyclohexadiene monoepoxide. This step has been optimized

  (R)-(+)- 和 (S)-(-)-4-methyl-2-cyclohexen-1-one 的首次催化不对称合成以及 (1S,4S) 的两种对映体的新的和改进的合成-(-) 和 (1R,4R)-(+)-4-methyl-2-cyclohexen-1-ol 以多克规模开发。该方法的关键步骤是将 Me2Zn（SN2'-途径）不对称催化加成到外消旋的 1,3-环己二烯单环氧化物中。该步骤已针对对映选择性和区域选择性以及后处理程序进行了优化。本文报道的 2,2'-联萘基亚磷酰胺的手性铜络合物所表现出的引人注目的配体加速催化作用允许非常低的催化剂负载量 (0.6 mol%)。
• Highly Enantioselective Regiodivergent and Catalytic Parallel Kinetic Resolution
  作者：Fabio Bertozzi、Paolo Crotti、Franco Macchia、Mauro Pineschi、Ben L. Feringa

  DOI：10.1002/1521-3773(20010302)40:5<930::aid-anie930>3.0.co;2-7

  日期：2001.3.2

  Chiral recognition leads to enantio- and regiodivergent reactivity: An unusual regiodivergent catalytic kinetic resolution has been accomplished for the first time in an organometallic reaction in which a C-C bond is formed. Chiral copper complexes of the non-racemic phosphoramidite ligand L* discriminate the enantiomers of semirigid vinyloxiranes (having a blocked s-cis or s-trans conformation) to

  手性识别导致对映和区域发散反应性：在形成CC键的有机金属反应中，首次实现了异常的区域发散性催化动力学拆分。非外消旋亚磷酰胺配体L *的手性铜配合物可区分半刚性乙烯基环氧乙烷（具有封闭的s-顺式或s-反式构象）的对映异构体，从而在两步过程中得到具有很高立体控制性的可分离的区域异构体产物。
• Copper-Catalyzed Highly Enantioselective Synthesis of Cyclic Allylic and Homoallylic Alcohols with Dialkylzinc Reagents
  作者：Mauro Pineschi、Federica Del Moro、Paolo Crotti、Valeria Di Bussolo、Franco Macchia

  DOI：10.1055/s-2004-834864

  日期：——

  The copper-phosphoramidite catalyzed addition of dialkylzinc reagents to racemic or meso allylic epoxides can be synthetically exploited in different ways, depending on the substrates and reaction conditions used.

  取决于所用的底物和反应条件，可以以不同的方式综合利用铜-亚磷酰胺催化的二烷基锌试剂与外消旋或内消旋烯丙基环氧化物的加成。
• Catalytic Regiodivergent Kinetic Resolution of Allylic Epoxides:  A New Entry to Allylic and Homoallylic Alcohols with High Optical Purity
  作者：Mauro Pineschi、Federica Del Moro、Paolo Crotti、Valeria Di Bussolo、Franco Macchia

  DOI：10.1021/jo035674h

  日期：2004.3.1

  A novel regiodivergent kinetic resolution of a series of allylic epoxides with alkylzinc reagents is described. Results demonstrate the potential of chiral copper-phosphoramidite catalysts for enantiomer differentiation of allylic epoxides, allowing a chiral catalyst-stereoregulated synthesis of cyclic allylic and homoallylic alcohols with high optical purities.