(1R,1R')-1-(cyclohex-2-enyl)ethanol | 95674-80-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,1R')-1-(cyclohex-2-enyl)ethanol
• 英文别名: (1R,1'R)-(+)-1-(2-cyclohexenyl)-1-ethanol；(1R)-1-[(1R)-cyclohex-2-en-1-yl]ethanol
• CAS: 95674-80-9
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: FRVOBIGHGFLOGN-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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,1R')-1-(cyclohex-2-enyl)ethanol 在 palladium on activated charcoal H₂₁ 作用下， 以 甲醇 为溶剂， 以91%的产率得到(R)-1-cyclohexylethanol
  参考文献：
  名称：

  Brown, Herbert C.; Bhat, Krishna S.; Jadhav, Prabhakar K., Journal of the Chemical Society. Perkin transactions I, 1991, p. 2633 - 2638

  摘要：

  DOI：
• 作为产物：
  描述：

  在 三氟化硼乙醚 、 异丁醛 作用下， 反应 12.0h， 以84%的产率得到(+)-α-蒎烯
  参考文献：
  名称：

  Chiral synthesis via organoboranes. 35. Simple procedures for the efficient recycling of the terpenyl chiral auxiliaries and convenient isolation of the homoallylic alcohols in asymmetric allyl- and crotylboration of aldehydes

  摘要：

  Asymmetric allyl- and crotylboration of aldehydes, RCHO, with terpenyl-based allyl- and crotylborane reagents Ter2*BAll (1), Ter2*BCrtZ (2), and Ter2*BCrtE (3, Ter* = Ipc, 4-Icr and 2-Icr; All = allyl and Crt = crotyl), afford Ter2*BOCH*(R)C*(1R)(2R)CH=CH2 intermediates 4. In these reactions, the isolation of homoallylic alcohols, HOCH*(R)C*(1R)(2R)CH--CH2 (5), can be accomplished via oxidation of 4 with alkaline hydrogen peroxide. Unfortunately, oxidative workup destroys the chiral auxiliary and produces a large amount of nonrecyclable byproduct, terpenol (Ter*OH). Further, isolation of the pure homoallylic alcohol by distillation can be difficult if it boils in the range of the abundant byproduct. Therefore, in order to recycle the chiral auxiliaries and isolate the product homoallylic alcohols in an efficient manner, we have developed the following procedures: (1) elimination workup, in which enantiomerically pure alpha-pinene and DELTA2- and DELTA3-carenes are liberated from terpenylborinates 4 by treatment with isobutyraldehyde and 1 mol % BF3.OEt2; (2) ethanolamine workup involving treatment of 4 with ethanolamine (EA) to achieve the precipitation of the ethanolamine adducts (EA-BTer2*, Ter* = Ipc and 2-Icr, 11 and 12) from which the Ter2*BOMe can be easily regenerated; and (3) 8-hydroxyquinoline workup, involving treatment of 4 with 8-hydroxyquinoline (8-HQ) to precipitate the 8-HQ adducts (8-HQ-BTer2*, Ter* = Ipc, 4-Icr and 2-Icr, 13-15), from which the various Ter2*BOMe intermediates can be conveniently liberated. It is hoped that these procedures will significantly enhance the scope of asymmetric allyl-/crotylboration of aldehydes with Ter2*BAll (1), Ter2*BCrtZ (2), and Ter2*BCrtE (3) and serve as excellent alternatives for any catalytic versions yet to be discovered.

  DOI：

  10.1021/jo00050a044

文献信息

• An asymmetric synthesis of the diastereomeric 1-(2-cyclohexenyl)-1-alkanols in high optical purity via a stereochemically stable allylic borane, B-2-cyclohexen-1-yldiisopinocampheylborane
  作者：Herbert C. Brown、Prabhakar K. Jadhav、Krishna S. Bhat

  DOI：10.1021/ja00294a068

  日期：1985.4
• BROWN, H. C.;JADHAV, P. K.;BHAT, KRISHNA, S., J. AMER. CHEM. SOC., 1985, 107, N 8, 2564-2565
  作者：BROWN, H. C.、JADHAV, P. K.、BHAT, KRISHNA, S.

  DOI：——

  日期：——
• YOUNG, D.;KITCHING, W., AUSTRAL. J. CHEM., 1985, 38, N 12, 1767-1777
  作者：YOUNG, D.、KITCHING, W.

  DOI：——

  日期：——