4-(2R)-(2-hydroxypent-4-enoyl)-10,10-dimethyl-3-phenyl-3,4-diazatricyclo[5.2.1.0^1,5]decan-2-one

• 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: 4-(2R)-(2-hydroxypent-4-enoyl)-10,10-dimethyl-3-phenyl-3,4-diazatricyclo[5.2.1.0^1,5]decan-2-one
• 英文别名: (1S,5R,7R)-4-[(2R)-2-hydroxypent-4-enoyl]-10,10-dimethyl-3-phenyl-3,4-diazatricyclo[5.2.1.01,5]decan-2-one
• 化学式: C₂₁H₂₆N₂O₃
• 分子量: 354.449
• InChiKey: BPMWJDBLZFTZDP-OILHZVAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  7,7-dimethyl-2'-phenyl-pyrazol-3'-one-bicyclo[2.2.1]heptane 在 europium(III) trifluoroacetate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.42h， 生成 4-(2R)-(2-hydroxypent-4-enoyl)-10,10-dimethyl-3-phenyl-3,4-diazatricyclo[5.2.1.0^1,5]decan-2-one
  参考文献：
  名称：

  Highly diastereoselective allylation and reduction of chiral camphor-derived α-ketoamides

  摘要：

  The diastercoselective allylation and reduction of camphor-derivcd alpha-ketoamides to give optically enriched a-hydroxyl amides with high to excellent stereoselectivities are described. Allylation was carried out using allyltributylstannane in the presence of a stoichiometric amount of a Lewis acid to afford the desired homoallylic alcohols in relatively high chemical yields (up to 98%) and stereoselectivities (LIP to 98% de). Diastereoselective reductions were performed with the relatively bulky hydride K-Selectride at -78 degrees C to give the corresponding a-hydroxy amides in excellent chemical yields (LIP to 98%) and stereoselectivities (up to 98% de). The absolute configuration of the new stereogenic center of the major diastereomer was established by X-ray crystallographic analysis. Finally, stereochemical induction and the Lewis acid dependent reversal of stereoselectivity is described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.01.011

文献信息

• Highly diastereoselective allylation and reduction of chiral camphor-derived α-ketoamides
  作者：Neelesh A. Kulkarni、Shy-Guey Wang、Li-Chen Lee、Huei Ru Tsai、Uppala Venkatesham、Kwunmin Chen

  DOI：10.1016/j.tetasy.2006.01.011

  日期：2006.2

  The diastercoselective allylation and reduction of camphor-derivcd alpha-ketoamides to give optically enriched a-hydroxyl amides with high to excellent stereoselectivities are described. Allylation was carried out using allyltributylstannane in the presence of a stoichiometric amount of a Lewis acid to afford the desired homoallylic alcohols in relatively high chemical yields (up to 98%) and stereoselectivities (LIP to 98% de). Diastereoselective reductions were performed with the relatively bulky hydride K-Selectride at -78 degrees C to give the corresponding a-hydroxy amides in excellent chemical yields (LIP to 98%) and stereoselectivities (up to 98% de). The absolute configuration of the new stereogenic center of the major diastereomer was established by X-ray crystallographic analysis. Finally, stereochemical induction and the Lewis acid dependent reversal of stereoselectivity is described. (c) 2006 Elsevier Ltd. All rights reserved.