(2R,3R,6R)-2-((S)-Hydroxy-phenyl-methyl)-6-isopropyl-3-methyl-cyclohexanone | 502687-12-9

• 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: (2R,3R,6R)-2-((S)-Hydroxy-phenyl-methyl)-6-isopropyl-3-methyl-cyclohexanone
• 英文别名: (2R,3R,6R)-2-[(S)-hydroxy(phenyl)methyl]-3-methyl-6-propan-2-ylcyclohexan-1-one
• CAS: 502687-12-9
• 化学式: C₁₇H₂₄O₂
• 分子量: 260.376
• InChiKey: DAIHUVWGUFLJIH-DTZQCDIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3R,6R)-2-((S)-Hydroxy-phenyl-methyl)-6-isopropyl-3-methyl-cyclohexanone 在 palladium on activated charcoal diazobis(pyridine) zinc 、 四溴环己二烯-1-酮 、 氢气 、 三苯基膦 作用下， 生成 2-Diphenylphosphanyl-N-[(R)-((1R,3R,6R)-3-isopropyl-6-methyl-2-oxo-cyclohexyl)-phenyl-methyl]-benzamide
  参考文献：
  名称：

  Synthesis, Stereostructure, and Conformations of Novel Bi- and Trifunctional (+)-Isomenthone Derivatives

  摘要：

  [GRAPHICS]Following protection, keto alcohols 4 [from (+)-isomenthone] undergo reduction to 1,3-diol 6 (S configuration at the new stereocenter). Organometallic C-nucleophiles add to the carbonyl with the same facial selectivity as hydride, providing multifunctional derivatives, e.g., 8 and 9, with five contiguous stereocenters. The side chain hydroxyl of 4 is elaborated into amino and amide derivatives (e.g., 12). Structural analysis shows that 6, 8, 9, and the precursor to 12 (10) all adopt triaxial solid-state conformations.

  DOI：

  10.1021/ol027434e
• 作为产物：
  描述：

  苯甲醛 、 (+)-异薄荷酮 在 lithium diisopropyl amide 作用下， 生成 (2R,3R,6R)-2-((S)-Hydroxy-phenyl-methyl)-6-isopropyl-3-methyl-cyclohexanone 、 (2R,3R,6R)-2-((R)-Hydroxy-phenyl-methyl)-6-isopropyl-3-methyl-cyclohexanone
  参考文献：
  名称：

  （+）-异薄荷酮醛醇缩合反应和非对映选择性逆转的新同手性酮醇

  摘要：

  （+）-异薄荷酮烯酸锂与芳基和烷基醛的醛醇缩合反应在α-碳（C6）上进行完全非对映异构控制，但在仲醇立体中心（通过X射线晶体结构测定确定）的立体化学结果可能出乎意料通过改变反应淬火温度来逆转。这提供了通往一系列新的同手性酮醇的途径。

  DOI：

  10.1016/s0040-4039(97)10430-0

文献信息

• Synthesis, Stereostructure, and Conformations of Novel Bi- and Trifunctional (+)-Isomenthone Derivatives
  作者：John M. Gardiner、Philip D. Crewe、Gillian E. Smith、Kenneth T. Veal、Robin G. Pritchard、John E. Warren

  DOI：10.1021/ol027434e

  日期：2003.2.1

  [GRAPHICS]Following protection, keto alcohols 4 [from (+)-isomenthone] undergo reduction to 1,3-diol 6 (S configuration at the new stereocenter). Organometallic C-nucleophiles add to the carbonyl with the same facial selectivity as hydride, providing multifunctional derivatives, e.g., 8 and 9, with five contiguous stereocenters. The side chain hydroxyl of 4 is elaborated into amino and amide derivatives (e.g., 12). Structural analysis shows that 6, 8, 9, and the precursor to 12 (10) all adopt triaxial solid-state conformations.
• New homochiral ketoalcohols from aldol reactions of (+)-isomenthone and reversal of diastereoselectivity
  作者：Jameel H. Chughtai、John M. Gardiner、Steven G. Harris、Simon Parsons、David W.H. Rankin、Carl H. Schwalbe

  DOI：10.1016/s0040-4039(97)10430-0

  日期：1997.12

  Aldol reaction of (+)-isomenthone lithium enolate with aryl and alkyl aldehydes proceeds with complete diastereocontrol at the α-carbon (C6), but the stereochemical outcome at the secondary alcohol stereocentre (established by X-ray crystal structure determinations) can be unexpectedly reversed by changing reaction quenching temperature. This provides a route to a range of new homochiral ketoalcohols

  （+）-异薄荷酮烯酸锂与芳基和烷基醛的醛醇缩合反应在α-碳（C6）上进行完全非对映异构控制，但在仲醇立体中心（通过X射线晶体结构测定确定）的立体化学结果可能出乎意料通过改变反应淬火温度来逆转。这提供了通往一系列新的同手性酮醇的途径。