benzylidenacetone acetohydrazone | 308134-44-3

• 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: benzylidenacetone acetohydrazone
• 英文别名: N'-(1-Methyl-3-phenyl-2-propenylidene)acetohydrazide；N-[(E)-[(E)-4-phenylbut-3-en-2-ylidene]amino]acetamide
• CAS: 308134-44-3
• 化学式: C₁₂H₁₄N₂O
• 分子量: 202.256
• InChiKey: HEGJEOJCUMZSJB-PEGOPYGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzylidenacetone acetohydrazone 在 dimethylamine borane 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.7h， 以92%的产率得到N'-(3-phenyl-1-methyl-2-propenyl)-acetohydrazide
  参考文献：
  名称：

  1,2-Reduction of α,β-unsaturated hydrazones using dimethylamine–borane/p-toluenesulfonic acid: an easy route to allyl hydrazines

  摘要：

  alpha,beta-Unsaturated hydrazones can be easily converted into N-allyl hydrazines by reaction with dimethylamine-borane/p-toluenesulfonic acid under mild reaction conditions. The reduction works well for N'-allyhydrazides but N'-allyl-N,N-dimethylhydrazines are rapidly reoxidised by air and so need to be manipulated under an inert atmosphere prior to M-acylation. Competitive conjugate reduction can also be observed and the regioselectivity of the dimethylamine-borane attack is determined by steric and/or electronic factors. The procedure is also effective for the C=N reduction of unconjugated hydrazones. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00914-6

文献信息

• Process for producing 1-acyl-2-pyrazoline derivatives
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0322691A1

  公开（公告）日：1989-07-05

  1-Acyl-2-pyrazoline derivatives represented by the formula where R¹ denotes a hydrogen atom, pyridyl group, pyrazinyl group, alkyl group, aryl group, or alkoxy group; and R², R³, and R⁴ independently denote a hydrogen atom, furyl group, pyridyl group, alkyl group, or aryl group, are produced by cyclizing by heating an acylhydrazone derivative represented by the formula where R¹, R², R³, and R⁴ are defined as above, to produce compounds having useful anti-cerebral edema activity.

  1-酰基-2-吡唑啉衍生物，由式表示 式中 R¹表示氢原子、吡啶基、吡嗪基、烷基、芳基或烷氧基；R²、R³和R⁴独立地表示氢原子、糠基、吡啶基、烷基或芳基，通过加热环化由式表示的酰基腙衍生物而制得。 其中 R¹、R²、R³ 和 R⁴ 的定义同上，从而制得具有有效抗脑水肿活性的化合物。
• US4895947A
  申请人：——

  公开号：US4895947A

  公开（公告）日：1990-01-23
• 1,2-Reduction of α,β-unsaturated hydrazones using dimethylamine–borane/p-toluenesulfonic acid: an easy route to allyl hydrazines
  作者：Maria E Casarini、Franco Ghelfi、Emanuela Libertini、Ugo M Pagnoni、Andrew F Parsons

  DOI：10.1016/s0040-4020(02)00914-6

  日期：2002.9

  alpha,beta-Unsaturated hydrazones can be easily converted into N-allyl hydrazines by reaction with dimethylamine-borane/p-toluenesulfonic acid under mild reaction conditions. The reduction works well for N'-allyhydrazides but N'-allyl-N,N-dimethylhydrazines are rapidly reoxidised by air and so need to be manipulated under an inert atmosphere prior to M-acylation. Competitive conjugate reduction can also be observed and the regioselectivity of the dimethylamine-borane attack is determined by steric and/or electronic factors. The procedure is also effective for the C=N reduction of unconjugated hydrazones. (C) 2002 Elsevier Science Ltd. All rights reserved.