2-[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]acetonitrile | 421598-91-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]acetonitrile
• CAS: 421598-91-6
• 化学式: C₉H₁₄N₂O
• 分子量: 166.223
• InChiKey: KABSIHUWEVICKW-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  45.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]acetonitrile 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 反应 12.0h， 生成 3-(benzenesulfonyl)-1-[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]-2-phenylcyclohexane-1-carbonitrile
  参考文献：
  名称：

  Asymmetric conjugate additions to chiral α,β-unsaturated oxazolines with sulfonyl carbanions

  摘要：

  Addition of sulfonyl carbanions with or without an electrophilic tether has been shown, under certain conditions, to add to alpha,beta-unsaturated oxazolines in good yields and high de's. When 4-bromobutylsulfonyl carbanions are added to unsaturated oxazolines, three contiguous stereocenters are formed and good yields of 1,2,3-substituted cyclohexanes are obtained as a 5:1 mixture of only two diastereomers. The sulfonyl substituent may be reductively cleaved to form selectively 1,2-disubstituted cyclohexanes. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)01151-6
• 作为产物：
  描述：

  L-叔亮氨醇 、 2-氰基乙脒酸乙酯盐酸盐 以 二氯甲烷 为溶剂， 反应 12.0h， 以85%的产率得到2-[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]acetonitrile
  参考文献：
  名称：

  Asymmetric conjugate additions to chiral α,β-unsaturated oxazolines with sulfonyl carbanions

  摘要：

  Addition of sulfonyl carbanions with or without an electrophilic tether has been shown, under certain conditions, to add to alpha,beta-unsaturated oxazolines in good yields and high de's. When 4-bromobutylsulfonyl carbanions are added to unsaturated oxazolines, three contiguous stereocenters are formed and good yields of 1,2,3-substituted cyclohexanes are obtained as a 5:1 mixture of only two diastereomers. The sulfonyl substituent may be reductively cleaved to form selectively 1,2-disubstituted cyclohexanes. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)01151-6

文献信息

• Asymmetric conjugate additions to chiral α,β-unsaturated oxazolines with sulfonyl carbanions
  作者：Laura F Basil、A.I Meyers、A Hassner

  DOI：10.1016/s0040-4020(01)01151-6

  日期：2002.1

  Addition of sulfonyl carbanions with or without an electrophilic tether has been shown, under certain conditions, to add to alpha,beta-unsaturated oxazolines in good yields and high de's. When 4-bromobutylsulfonyl carbanions are added to unsaturated oxazolines, three contiguous stereocenters are formed and good yields of 1,2,3-substituted cyclohexanes are obtained as a 5:1 mixture of only two diastereomers. The sulfonyl substituent may be reductively cleaved to form selectively 1,2-disubstituted cyclohexanes. (C) 2002 Published by Elsevier Science Ltd.