(2R,3R,6R)-2-((R)-Azido-phenyl-methyl)-6-isopropyl-3-methyl-cyclohexanone | 502687-01-6

• 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-((R)-Azido-phenyl-methyl)-6-isopropyl-3-methyl-cyclohexanone
• 英文别名: (2R,3R,6R)-2-[(R)-azido(phenyl)methyl]-3-methyl-6-propan-2-ylcyclohexan-1-one
• CAS: 502687-01-6
• 化学式: C₁₇H₂₃N₃O
• 分子量: 285.389
• InChiKey: KTHYWCXHZQRROK-MIGQKNRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R,6R)-2-((R)-Azido-phenyl-methyl)-6-isopropyl-3-methyl-cyclohexanone 在 palladium on activated charcoal 氢气 作用下， 以31%的产率得到(2R,3R,6R)-2-((R)-Amino-phenyl-methyl)-6-isopropyl-3-methyl-cyclohexanone
  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：

  (2R,3R,6R)-2-((S)-Hydroxy-phenyl-methyl)-6-isopropyl-3-methyl-cyclohexanone 在 diazobis(pyridine) zinc 、 四溴环己二烯-1-酮 、 三苯基膦 作用下， 以77%的产率得到(2R,3R,6R)-2-((R)-Azido-phenyl-methyl)-6-isopropyl-3-methyl-cyclohexanone
  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

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.