1,1-dibenzyl-2-(3-(tert-butyldimethylsilyloxy)propylidene)hydrazine | 939045-80-4

• 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: 1,1-dibenzyl-2-(3-(tert-butyldimethylsilyloxy)propylidene)hydrazine
• CAS: 939045-80-4
• 化学式: C₂₃H₃₄N₂OSi
• 分子量: 382.621
• InChiKey: LZKQWTFYXKEECW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  27.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  24.83
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,1-dibenzyl-2-(3-(tert-butyldimethylsilyloxy)propylidene)hydrazine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以89%的产率得到3-(N,N-dibenzylhydrazono)propan-1-ol
  参考文献：
  名称：

  Enhanced reactivity in radical cyclizations of hydrazones using the silicon-tethered 1-bromovinyl group

  摘要：

  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.

  DOI：

  10.1016/j.tet.2007.03.017
• 作为产物：
  描述：

  3-(叔丁基-二甲基-硅烷基OXY)-丙醛 、 1,1-二苄肼 在 magnesium sulfate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以85%的产率得到1,1-dibenzyl-2-(3-(tert-butyldimethylsilyloxy)propylidene)hydrazine
  参考文献：
  名称：

  Enhanced reactivity in radical cyclizations of hydrazones using the silicon-tethered 1-bromovinyl group

  摘要：

  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.

  DOI：

  10.1016/j.tet.2007.03.017