(E,E)-bis-(2,2-dimethyl-propylidene)-hydrazine | 1522-05-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E,E)-bis-(2,2-dimethyl-propylidene)-hydrazine
• 英文别名: 2,2-dimethyl-propionaldehyde (E,E)-azine；anti-anti-Trimethylacetaldazin；(E,E)-pivalaldazine；(E)-N-[(E)-2,2-dimethylpropylideneamino]-2,2-dimethylpropan-1-imine
• CAS: 1522-05-0
• 化学式: C₁₀H₂₀N₂
• 分子量: 168.282
• InChiKey: FQKCIYLEQYBWAA-MKICQXMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苄氧基乙酰氯 、 (E,E)-bis-(2,2-dimethyl-propylidene)-hydrazine 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以74%的产率得到cis-3-Benzyloxy-4-tert-butyl-1-neo-pentylideneamino-2-azetidinone
  参考文献：
  名称：

  2,3-Diaza-1,3-dienes (Azines) as Substrates for the Staudinger Reaction. Synthesis and Reactivity of N-Imino-.beta.-lactams

  摘要：

  The reaction of aromatic and aliphatic azines with different ketene precursors, such as the acid chloride/Et(3)N system, alkoxychromium(0) carbenes, and free diphenyl ketene, gives N-imino-beta-lactams in good to excellent yields, with good levels of cis,trans-selectivity. A wide variety of symmetrically-substituted azines derived from aldehydes and ketones are compatible with the Staudinger reaction. Chiral N-imino-beta-lactams derived from symmetrically or unsymmetrically (mixed) chiral azines are also obtained in good yields as essentially single enantiomers (de > 95%). Different reaction intermediates, including hemiaminals, oxadiazols, and hydrazides have been isolated. Free diphenyl ketene forms Diels-Alder adducts and N-acylazadienes in addition to the previously reported N-imino-beta-lactams, The usual reactivity of the beta-lactam ring is modified in N-imino-beta-lactams by the presence of the imino group. Thus, beta-hydrazonoesters, N-alkylamino-beta-lactams, and NH-beta-lactams can be efficiently obtained by base-catalyzed 2-azetidinone ring opening, catalytic hydrogenation, and ozonolysis, respectively.

  DOI：

  10.1021/jo00105a014
• 作为产物：
  描述：

  特戊醛 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 (E,E)-bis-(2,2-dimethyl-propylidene)-hydrazine
  参考文献：
  名称：

  2,3-Diaza-1,3-dienes (Azines) as Substrates for the Staudinger Reaction. Synthesis and Reactivity of N-Imino-.beta.-lactams

  摘要：

  The reaction of aromatic and aliphatic azines with different ketene precursors, such as the acid chloride/Et(3)N system, alkoxychromium(0) carbenes, and free diphenyl ketene, gives N-imino-beta-lactams in good to excellent yields, with good levels of cis,trans-selectivity. A wide variety of symmetrically-substituted azines derived from aldehydes and ketones are compatible with the Staudinger reaction. Chiral N-imino-beta-lactams derived from symmetrically or unsymmetrically (mixed) chiral azines are also obtained in good yields as essentially single enantiomers (de > 95%). Different reaction intermediates, including hemiaminals, oxadiazols, and hydrazides have been isolated. Free diphenyl ketene forms Diels-Alder adducts and N-acylazadienes in addition to the previously reported N-imino-beta-lactams, The usual reactivity of the beta-lactam ring is modified in N-imino-beta-lactams by the presence of the imino group. Thus, beta-hydrazonoesters, N-alkylamino-beta-lactams, and NH-beta-lactams can be efficiently obtained by base-catalyzed 2-azetidinone ring opening, catalytic hydrogenation, and ozonolysis, respectively.

  DOI：

  10.1021/jo00105a014

文献信息

• Rapid Access to Diverse Arrays of Chiral 3,4-Diazaphospholanes
  作者：Clark R. Landis、Wiechang Jin、Jonathan S. Owen、Thomas P. Clark

  DOI：10.1002/1521-3773(20010917)40:18<3432::aid-anie3432>3.0.co;2-3

  日期：2001.9.17
• Elguero,J. et al., Bulletin de la Societe Chimique de France, 1968, p. 713 - 731
  作者：Elguero,J. et al.

  DOI：——

  日期：——
• QUAST H.; KEES F., CHEM. BER., 1981, 114, NO 2, 787-801
  作者：QUAST H.、 KEES F.

  DOI：——

  日期：——
• QUAST H.; KEES F., CHEM. BER., 1981, 114, NO 2, 802-807
  作者：QUAST H.、 KEES F.

  DOI：——

  日期：——
• US3939147A
  申请人：——

  公开号：US3939147A

  公开（公告）日：1976-02-17