[(2R)-1-(cyclohexen-1-yl)pyrrolidin-2-yl]methoxy-trimethylsilane | 256442-05-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: [(2R)-1-(cyclohexen-1-yl)pyrrolidin-2-yl]methoxy-trimethylsilane
• CAS: 256442-05-4
• 化学式: C₁₄H₂₇NOSi
• 分子量: 253.46
• InChiKey: LVFLLKUEWRROTL-CQSZACIVSA-N

物化性质

• 沸点：
  310.2±21.0 °C(Predicted)
• 密度：
  0.960±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丙烯腈 、 [(2R)-1-(cyclohexen-1-yl)pyrrolidin-2-yl]methoxy-trimethylsilane 在 magnesium chloride 作用下， 以 苯 为溶剂， 以48%的产率得到3-(2-oxocyclohexyl)propionitrile
  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：

  D-脯氨醇 、 alkaline earth salt of/the/ methylsulfuric acid 生成 [(2R)-1-(cyclohexen-1-yl)pyrrolidin-2-yl]methoxy-trimethylsilane
  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

• ITO, YOSHIHIKO;SAWAMURA, MASAYA;KOMINAMI, KAZUHIKO;SAEGUSA, TAKEO, TETRAHEDRON LETT., 1985, 26, N 43, 5303-5306
  作者：ITO, YOSHIHIKO、SAWAMURA, MASAYA、KOMINAMI, KAZUHIKO、SAEGUSA, TAKEO

  DOI：——

  日期：——
• 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.