(R)-3-((S)-(benzyloxy)(phenyl)methyl)hex-5-en-2-one | 1453837-63-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3-((S)-(benzyloxy)(phenyl)methyl)hex-5-en-2-one
• 英文别名: (3R)-3-[(S)-phenyl(phenylmethoxy)methyl]hex-5-en-2-one
• CAS: 1453837-63-2
• 化学式: C₂₀H₂₂O₂
• 分子量: 294.393
• InChiKey: AVURYEUPVNRYNP-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-3-((S)-(benzyloxy)(phenyl)methyl)hex-5-en-2-one 、 1-溴-3-甲基-2-丁烯 在 lithium diisopropyl amide 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.75h， 以95%的产率得到(R)-4-((S)-(benzyloxy)(phenyl)methyl)-9-methyldeca-1,8-dien-5-one
  参考文献：
  名称：

  Expanding the scope of the asymmetric anti-aldol addition of chiral N-amino cyclic carbamate hydrazones

  摘要：

  An asymmetric anti-aldol addition process of ketone-derived donors that is not limited by the structure of the ketone is described. This is achieved by merging the enantioselective alpha,alpha-bisalkylation of N-amino cyclic carbamate (ACC) hydrazones with the asymmetric anti-aldol addition of ACC hydrazones. The products of this process are obtained with essentially perfect stereoselectivity. Using this procedure it is possible to gain access to ketone-based anti-aldol addition products that are inaccessible in a controlled sense via direct aldol methods. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.140
• 作为产物：
  描述：

  苄基碘 在 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 20.75h， 生成 (R)-3-((S)-(benzyloxy)(phenyl)methyl)hex-5-en-2-one
  参考文献：
  名称：

  Expanding the scope of the asymmetric anti-aldol addition of chiral N-amino cyclic carbamate hydrazones

  摘要：

  An asymmetric anti-aldol addition process of ketone-derived donors that is not limited by the structure of the ketone is described. This is achieved by merging the enantioselective alpha,alpha-bisalkylation of N-amino cyclic carbamate (ACC) hydrazones with the asymmetric anti-aldol addition of ACC hydrazones. The products of this process are obtained with essentially perfect stereoselectivity. Using this procedure it is possible to gain access to ketone-based anti-aldol addition products that are inaccessible in a controlled sense via direct aldol methods. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.140

文献信息

• Expanding the scope of the asymmetric anti-aldol addition of chiral N-amino cyclic carbamate hydrazones
  作者：John D. Knight、Don M. Coltart

  DOI：10.1016/j.tetlet.2013.07.140

  日期：2013.10

  An asymmetric anti-aldol addition process of ketone-derived donors that is not limited by the structure of the ketone is described. This is achieved by merging the enantioselective alpha,alpha-bisalkylation of N-amino cyclic carbamate (ACC) hydrazones with the asymmetric anti-aldol addition of ACC hydrazones. The products of this process are obtained with essentially perfect stereoselectivity. Using this procedure it is possible to gain access to ketone-based anti-aldol addition products that are inaccessible in a controlled sense via direct aldol methods. (C) 2013 Elsevier Ltd. All rights reserved.