1-(10,10-dimethyl-2-oxo-3-phenyl-3,4-diazatricyclo[5.2.1.0^1,5]dec-4-yl)-2-phenylethane-1,2-dione | 756499-83-9

• 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: 1-(10,10-dimethyl-2-oxo-3-phenyl-3,4-diazatricyclo[5.2.1.0^1,5]dec-4-yl)-2-phenylethane-1,2-dione
• 英文别名: 1-[(1S,5R,7R)-10,10-dimethyl-2-oxo-3-phenyl-3,4-diazatricyclo[5.2.1.01,5]decan-4-yl]-2-phenylethane-1,2-dione
• CAS: 756499-83-9
• 化学式: C₂₄H₂₄N₂O₃
• 分子量: 388.466
• InChiKey: IPNUBHOSUIDOLO-YJLYGGOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(10,10-dimethyl-2-oxo-3-phenyl-3,4-diazatricyclo[5.2.1.0^1,5]dec-4-yl)-2-phenylethane-1,2-dione 在 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以98%的产率得到4-(2S)-(2-hydroxy-2-phenylacetyl)-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
• 作为产物：
  描述：

  苯甲酰甲酸 、 7,7-dimethyl-2'-phenyl-pyrazol-3'-one-bicyclo[2.2.1]heptane 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 以85%的产率得到1-(10,10-dimethyl-2-oxo-3-phenyl-3,4-diazatricyclo[5.2.1.0^1,5]dec-4-yl)-2-phenylethane-1,2-dione
  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

• Lewis acid mediated diastereoselective allylation of camphorpyrazolidinone derived α-ketoamides
  作者：Shy-Guey Wang、Huei Ru Tsai、Kwunmin Chen

  DOI：10.1016/j.tetlet.2004.05.146

  日期：2004.8

  Diastereoselective allylation of camphorpyrazolidinone derived alpha-ketoamides was examined using allyltributyltin in the presence of various Lewis acids. The corresponding optically enriched quarternary alpha-hydroxy carbonyls were obtained in reasonable to excellent material yields (51-95%) and with practical levels of stereoselectivity (up to >95% de) when a stoichiometric amount of Sn(OTf)(2) was used. The stereochemical induction is discussed. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.