isobutylidene-carbazic acid ethyl ester | 409316-75-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: isobutylidene-carbazic acid ethyl ester
• 英文别名: Isobutyraldehyd-(aethoxycarbonyl-hydrazon)；Isobutyliden-carbazidsaeure-aethylester；ethyl N-(2-methylpropylideneamino)carbamate
• CAS: 409316-75-2
• 化学式: C₇H₁₄N₂O₂
• 分子量: 158.2
• InChiKey: WXICPNWDHKYIKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  isobutylidene-carbazic acid ethyl ester 在 磺酰氯 、 sodium carbonate 作用下， 以 四氢呋喃 、 四氯化碳 、 乙腈 为溶剂， 反应 16.5h， 生成 Ethyl 3-[[dichloro(phenyl)-lambda4-selanyl]methyl]-5-propan-2-yl-3,4-dihydropyrazole-2-carboxylate
  参考文献：
  名称：

  Synthesis of pyrazolidine, 1-pyrazoline, 2-pyrazoline derivatives by selenium-induced cyclization of homoallylhydrazines

  摘要：

  The PhSeBr-induced cyclization of N'-but-3-en-1-yl ethoxycarbonylhydrazines 1, phenylhydrazines 2 and dimethylhydrazines 3 has been studied. A 5-exo-trig ring closure occurred in each case and phenylselanyimethyl-pyrazolidines 4, 2-pyrazolines 5 and 10, 1-pyrazolines 8 and pyrazolidinium bromides 11 were synthesized. Radical deselenenylation has allowed the preparation of 5-methylpyrazolidines 12 and 5-methyl-2-pyrazolines 13 and 14. Decomposition of the dibromoselenuranes derived from 2-pyrazolines 5 and 10 afforded bromomethyl derivatives. With 1-phenyl-2-pyrazolines 10, an electrophilic p-halogenation of the phenyl nucleus was observed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01064-x
• 作为产物：
  描述：

  异丁醛 、 肼基甲酸乙酯 以 甲醇 为溶剂， 反应 12.0h， 以94%的产率得到isobutylidene-carbazic acid ethyl ester
  参考文献：
  名称：

  拟肽模拟β-内酰胺分子的合成作为潜在的蛋白酶抑制剂。

  摘要：

  报道了用于构建新型拟肽结构的合成方法。该结构在肽主链中掺入了β-内酰胺和氮杂肽，目的是生成合理设计的基于底物的蛋白酶抑制剂。通过使丝氨酸或苏氨酸-氮杂肽经受Mitsunobu反应条件来形成β-内酰胺。重要的是，氮杂肽模拟物β-内酰胺结构允许扩展的结合抑制，并且描述了产生四肽模拟物结构的合成方法。

  DOI：

  10.1021/jo026280d

文献信息

• Carbazic Acid Esters as Carbonyl Reagents
  作者：Norman Rabjohn、H. D. Barnstorff

  DOI：10.1021/ja01105a513

  日期：1953.5
• Ugi,I.; Bodesheim,F., Justus Liebigs Annalen der Chemie, 1963, vol. 666, p. 61 - 64
  作者：Ugi,I.、Bodesheim,F.

  DOI：——

  日期：——
• The Synthesis of Azapeptidomimetic β-Lactam Molecules as Potential Protease Inhibitors
  作者：William P. Malachowski、Chenyang Tie、Katherine Wang、Robert L. Broadrup

  DOI：10.1021/jo026280d

  日期：2002.12.1

  Synthetic methods for the construction of a novel peptidomimetic structure are reported. The structure incorporates a beta-lactam and an azapeptide in a peptide backbone with the intention of generating rationally designed substrate-based protease inhibitors. The beta-lactam is formed by subjecting serine or threonine-azapeptides to Mitsunobu reaction conditions. Importantly, the azapeptidomimetic

  报道了用于构建新型拟肽结构的合成方法。该结构在肽主链中掺入了β-内酰胺和氮杂肽，目的是生成合理设计的基于底物的蛋白酶抑制剂。通过使丝氨酸或苏氨酸-氮杂肽经受Mitsunobu反应条件来形成β-内酰胺。重要的是，氮杂肽模拟物β-内酰胺结构允许扩展的结合抑制，并且描述了产生四肽模拟物结构的合成方法。
• Synthesis of pyrazolidine, 1-pyrazoline, 2-pyrazoline derivatives by selenium-induced cyclization of homoallylhydrazines
  作者：Michaël Ternon、Francis Outurquin、Claude Paulmier

  DOI：10.1016/s0040-4020(01)01064-x

  日期：2001.12

  The PhSeBr-induced cyclization of N'-but-3-en-1-yl ethoxycarbonylhydrazines 1, phenylhydrazines 2 and dimethylhydrazines 3 has been studied. A 5-exo-trig ring closure occurred in each case and phenylselanyimethyl-pyrazolidines 4, 2-pyrazolines 5 and 10, 1-pyrazolines 8 and pyrazolidinium bromides 11 were synthesized. Radical deselenenylation has allowed the preparation of 5-methylpyrazolidines 12 and 5-methyl-2-pyrazolines 13 and 14. Decomposition of the dibromoselenuranes derived from 2-pyrazolines 5 and 10 afforded bromomethyl derivatives. With 1-phenyl-2-pyrazolines 10, an electrophilic p-halogenation of the phenyl nucleus was observed. (C) 2001 Elsevier Science Ltd. All rights reserved.