(+/-)-N'-{(1E)-[2,2-dimethyl-1,3-dioxolan-4-yl]methylene}-(4-methylbenzenesulfonyl)hydrazine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-N'-{(1E)-[2,2-dimethyl-1,3-dioxolan-4-yl]methylene}-(4-methylbenzenesulfonyl)hydrazine
• 英文别名: N-[(E)-(2,2-dimethyl-1,3-dioxolan-4-yl)methylideneamino]-4-methylbenzenesulfonamide
• 化学式: C₁₃H₁₈N₂O₄S
• 分子量: 298.363
• InChiKey: UCLMHHQDZOIINH-RIYZIHGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  85.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-N'-{(1E)-[2,2-dimethyl-1,3-dioxolan-4-yl]methylene}-(4-methylbenzenesulfonyl)hydrazine 在 异丙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 (4S)-2,2-dimethyl-4-[(1Z)-4-phenylbut-1-enyl]-1,3-dioxolane 、 (4S)-2,2-dimethyl-4-[(1E)-4-phenylbut-1-enyl]-1,3-dioxolane 、 (4R)-2,2-dimethyl-4-[(1Z)-4-phenylbut-1-enyl]-1,3-dioxolane 、 (4R)-2,2-dimethyl-4-[(1E)-4-phenylbut-1-enyl]-1,3-dioxolane
  参考文献：
  名称：

  Olefination of α-Hydroxy or α-Aminoaldehyde Derivatives via Reaction of Their Arylsulfonylhydrazones with Sulfonyl Anions

  摘要：

  Reaction of tosylhydrazones of O-substituted a-hydroxy or N-substituted a-amino aldehydes (2, 7, 11, 15, 17, and 20) with selected alpha-magnesio alkyl phenyl sulfones afforded the respective derivatives of allylic alcohols or allylic amines. 2,3-O-Isopropylidene-D-glyceraldehyde (1) was transformed into its tosylhydrazone (2) and then olefins 4a with retention of optical purity.

  DOI：

  10.1021/jo0499118
• 作为产物：
  描述：

  对甲苯磺酰肼 、 丙酮缩甘油 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 以34%的产率得到(+/-)-N'-{(1E)-[2,2-dimethyl-1,3-dioxolan-4-yl]methylene}-(4-methylbenzenesulfonyl)hydrazine
  参考文献：
  名称：

  Olefination of α-Hydroxy or α-Aminoaldehyde Derivatives via Reaction of Their Arylsulfonylhydrazones with Sulfonyl Anions

  摘要：

  Reaction of tosylhydrazones of O-substituted a-hydroxy or N-substituted a-amino aldehydes (2, 7, 11, 15, 17, and 20) with selected alpha-magnesio alkyl phenyl sulfones afforded the respective derivatives of allylic alcohols or allylic amines. 2,3-O-Isopropylidene-D-glyceraldehyde (1) was transformed into its tosylhydrazone (2) and then olefins 4a with retention of optical purity.

  DOI：

  10.1021/jo0499118

文献信息

• Olefination of α-Hydroxy or α-Aminoaldehyde Derivatives via Reaction of Their Arylsulfonylhydrazones with Sulfonyl Anions
  作者：Jerzy Wicha、Andrzej Zarecki

  DOI：10.1021/jo0499118

  日期：2004.8.1

  Reaction of tosylhydrazones of O-substituted a-hydroxy or N-substituted a-amino aldehydes (2, 7, 11, 15, 17, and 20) with selected alpha-magnesio alkyl phenyl sulfones afforded the respective derivatives of allylic alcohols or allylic amines. 2,3-O-Isopropylidene-D-glyceraldehyde (1) was transformed into its tosylhydrazone (2) and then olefins 4a with retention of optical purity.