3-[(1S,2Z)-2-(methoxymethylidene)cyclohexyl]propanenitrile | 913945-79-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-[(1S,2Z)-2-(methoxymethylidene)cyclohexyl]propanenitrile
• CAS: 913945-79-6
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: MELWOMMUNXAPPQ-RGAIUGGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  33.02
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-[(1S,2Z)-2-(methoxymethylidene)cyclohexyl]propanenitrile 在 叔丁基二甲硅基三氟甲磺酸酯 、 氧气 、 亚甲兰 作用下， 以 二氯甲烷 为溶剂， 生成 (1S,6R,9S,12R)-9-(4-fluorophenyl)-12-methoxy-10,11,13-trioxatricyclo[7.2.2.01,6]tridecane
  参考文献：
  名称：

  Asymmetric syntheses of enantiomeric 3-p-fluorophenyl 1,2,4-trioxane analogues of the antimalarial artemisinin

  摘要：

  We have devised an asymmetric synthesis of chiral artemisinin analogues (+)-4a and (-)-4a that retain the tricyclic ring system found in the natural product. The key step in the preparation of (+)-4a involves an asymmetric MgCl2 promoted Michael addition of the (R)-(-)pyrrolidinemethanol-derived enamine 8 to acrylonitrile. This gives the corresponding ketone 9 in 50% yield (>95% ee). Subsequent elaboration of 9 provides the trioxane target (+)-4a in greater than 85% ee. Enantiomeric trioxane (-)-4a was prepared in a similar manner using S-(+)-pyrrolidinemethanol in the first step of the sequence. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01892-4
• 作为产物：
  描述：

  (S)-2-β-cyanoethylcyclohexanone 、 甲氧基甲基三苯基氯化膦 在 正丁基锂 作用下， 生成 3-[(1S,2Z)-2-(methoxymethylidene)cyclohexyl]propanenitrile 、
  参考文献：
  名称：

  Asymmetric syntheses of enantiomeric 3-p-fluorophenyl 1,2,4-trioxane analogues of the antimalarial artemisinin

  摘要：

  We have devised an asymmetric synthesis of chiral artemisinin analogues (+)-4a and (-)-4a that retain the tricyclic ring system found in the natural product. The key step in the preparation of (+)-4a involves an asymmetric MgCl2 promoted Michael addition of the (R)-(-)pyrrolidinemethanol-derived enamine 8 to acrylonitrile. This gives the corresponding ketone 9 in 50% yield (>95% ee). Subsequent elaboration of 9 provides the trioxane target (+)-4a in greater than 85% ee. Enantiomeric trioxane (-)-4a was prepared in a similar manner using S-(+)-pyrrolidinemethanol in the first step of the sequence. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01892-4

文献信息

• Asymmetric syntheses of enantiomeric 3-p-fluorophenyl 1,2,4-trioxane analogues of the antimalarial artemisinin
  作者：Paul M. O'Neill、Alison Miller、Jamie F. Bickley、Feodor Scheinmann、Chang Ho Oh、Gary H. Posner

  DOI：10.1016/s0040-4039(99)01892-4

  日期：1999.12

  We have devised an asymmetric synthesis of chiral artemisinin analogues (+)-4a and (-)-4a that retain the tricyclic ring system found in the natural product. The key step in the preparation of (+)-4a involves an asymmetric MgCl2 promoted Michael addition of the (R)-(-)pyrrolidinemethanol-derived enamine 8 to acrylonitrile. This gives the corresponding ketone 9 in 50% yield (>95% ee). Subsequent elaboration of 9 provides the trioxane target (+)-4a in greater than 85% ee. Enantiomeric trioxane (-)-4a was prepared in a similar manner using S-(+)-pyrrolidinemethanol in the first step of the sequence. (C) 1999 Elsevier Science Ltd. All rights reserved.