3-(Diphenyl-hydrazono)-propan-1-ol | 856243-00-0

• 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: 3-(Diphenyl-hydrazono)-propan-1-ol
• 英文别名: 3-(diphenylhydrazinylidene)propan-1-ol
• CAS: 856243-00-0
• 化学式: C₁₅H₁₆N₂O
• 分子量: 240.305
• InChiKey: DADWFXALZPYXQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.83
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(Diphenyl-hydrazono)-propan-1-ol 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 生成 N'-((2R,4R)-2-Ethoxy-tetrahydro-pyran-4-yl)-N,N-diphenyl-hydrazine
  参考文献：
  名称：

  Haloacetal Radical Cyclizations of α- and β-Hydroxyhydrazones

  摘要：

  Haloacetal radical cyclizations of α- and β-hydroxyhydrazones provide a direct access to aminosugarlike compounds. Stereocontrol of this process is influenced by stereogenic centers of both the hydroxyhydrazone and the acetal. The outcomes are consistent with chair and twist transition states with the anomeric alkoxy group in pseudoaxial orientations.

  DOI：

  10.1021/ol050663r
• 作为产物：
  描述：

  N-[3-[tert-butyl(dimethyl)silyl]oxypropylideneamino]-N-phenylaniline 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以76%的产率得到3-(Diphenyl-hydrazono)-propan-1-ol
  参考文献：
  名称：

  Haloacetal Radical Cyclizations of α- and β-Hydroxyhydrazones

  摘要：

  Haloacetal radical cyclizations of α- and β-hydroxyhydrazones provide a direct access to aminosugarlike compounds. Stereocontrol of this process is influenced by stereogenic centers of both the hydroxyhydrazone and the acetal. The outcomes are consistent with chair and twist transition states with the anomeric alkoxy group in pseudoaxial orientations.

  DOI：

  10.1021/ol050663r

文献信息

• Enhanced reactivity in radical cyclizations of hydrazones using the silicon-tethered 1-bromovinyl group
  作者：Gregory K. Friestad、Tao Jiang、Alex K. Mathies

  DOI：10.1016/j.tet.2007.03.017

  日期：2007.5

  A silicon-tethered 1-bromovinyl group was shown to function as a radical precursor for tin-mediated vinyl additions to chiral alpha- or beta-hydroxyhydrazone. In contrast to related thiyl-mediated methods, these vinyl bromides were not limited to the 5-exo cyclization mode. A series of Si-tethered 5-exo and 6-exo cyclizations formed the corresponding five- and six-membered exo-methylene- substituted oxasilacycles. Treatment with fluoride cleaved the Si-C and Si-O bonds to afford the corresponding allylic hydrazines. Diastereoselectivities ranged from 2:1 to 25:1 (anti:syn) for the 5-exo cyclizations, depending on the size of the exocyclic substituent, but 6-exo cyclization was not diastereoselective. A variant involving Tamao oxidation of the exo-methylene oxasilacyclopentane intermediate afforded a methyl ketone, a net process corresponding to addition of a radical acyl anion equivalent. (C) 2007 Elsevier Ltd. All rights reserved.