pivalaldehyde semicarbazone | 23809-33-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: pivalaldehyde semicarbazone
• 英文别名: (2,2-Dimethylpropylideneamino)urea
• CAS: 23809-33-8
• 化学式: C₆H₁₃N₃O
• 分子量: 143.189
• InChiKey: VZQMUDUULDRAHS-UHFFFAOYSA-N

物化性质

• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  67.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  pivalaldehyde semicarbazone 在 碘 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 以67 mg的产率得到5-叔丁基-1,3,4-噁二唑-2-胺
  参考文献：
  名称：

  Synthesis of 2-Amino-1,3,4-oxadiazoles and 2-Amino-1,3,4-thiadiazoles via Sequential Condensation and I₂-Mediated Oxidative C–O/C–S Bond Formation

  摘要：

  2-Amino-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles were synthesized via condensation of semicarbazide/thiosemicarbazide and the corresponding aldehydes followed by I-2-mediated oxidative C-O/C-S bond formation. This transition-metal-free sequential synthesis process is compatible with aromatic, aliphatic, and cinnamic aldehydes, providing facile access to a variety of diazole derivatives bearing a 2-amino substituent in an efficient and scalable fashion.

  DOI：

  10.1021/jo502518c
• 作为产物：
  描述：

  盐酸氨基脲 、 特戊醛 在 sodium acetate 作用下， 反应 1.0h， 以82.5%的产率得到pivalaldehyde semicarbazone
  参考文献：
  名称：

  Passerini反应与α-内酰胺之间的直接联系

  摘要：

  α-内酰胺（叠氮ino烷）可以在Passerini反应中取代三种反应物中的两种，即氧代化合物和异腈。使四个α-内酰胺（5a - d）与正p K a值的单羧酸和二羧酸反应，分别得到2-酰氧基羧酰胺（4）和双-2-酰氧基羧酰胺产物12和13。还通过Passerini反应制备了相同的化合物。p K a p为负的酸将α-内酰胺脱羰，生成铵盐。反应的主要路径取决于p K a 酸成分，α-内酰胺的反应性和反应条件。

  DOI：

  10.1016/j.tet.2003.11.067

文献信息

• THE SYNTHESIS, PHYSICAL, AND SPECTRAL PROPERTIES, AND SOME REACTIONS OF A NEW STABLE<i>bis</i>-α-LACTAM (AZIRIDINONE) WITH A TERPENE SKELETON
  作者：Istvan Lengyel、Victor Cesare、Tony Taldone、David Uliss

  DOI：10.1081/scc-100107018

  日期：2001.1

  decomposition required 1h of reflux in boiling n-decane (b.p. 174°C) and the products are 2,2-dimethylpropanal (pivalaldehyde) (6) and 1,8-diisocyano-p-menthane (7). Reaction with benzylamine yielded the unexpected bis-benzylamide (13a), while reaction with sodium methoxide gave the bis-α-amino acid ester (14).

  合成一种新的稳定的双-α-内酰胺，cis-1,1'（p-menth-1,8-ylene）双（3-叔丁基-2-氮丙啶酮）（4），衍生自对薄荷烷, 进行了描述。完全自发热分解需要在沸腾的正癸烷（沸点 174°C）中回流 1 小时，产物为 2,2-二甲基丙醛（新戊醛）（6）和 1,8-二异氰基对薄荷烷（7）。与苄胺反应产生出乎意料的双苄基酰胺（13a），而与甲醇钠反应产生双-α-氨基酸酯（14）。
• Hydrolytic Stability of Hydrazones and Oximes
  作者：Jeet Kalia、Ronald T. Raines

  DOI：10.1002/anie.200802651

  日期：2008.9.15

  Hydrazones and oximes are common conjugates, but are labile to hydrolysis. The hydrolytic stability of isostructural hydrazones and an oxime have been determined at pD 5.0–9.0. The hydrolysis of each adduct was catalyzed by acid. Rate constants for oxime hydrolysis were nearly 103-fold lower than those for simple hydrazones; a trialkylhydrazonium ion (formed after condensation) was even more stable than the oxime. The data suggest a general mechanism for conjugate hydrolysis.
• Synthesis of 2-Amino-1,3,4-oxadiazoles and 2-Amino-1,3,4-thiadiazoles via Sequential Condensation and I₂-Mediated Oxidative C–O/C–S Bond Formation
  作者：Pengfei Niu、Jinfeng Kang、Xianhai Tian、Lina Song、Hongxu Liu、Jie Wu、Wenquan Yu、Junbiao Chang

  DOI：10.1021/jo502518c

  日期：2015.1.16

  2-Amino-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles were synthesized via condensation of semicarbazide/thiosemicarbazide and the corresponding aldehydes followed by I-2-mediated oxidative C-O/C-S bond formation. This transition-metal-free sequential synthesis process is compatible with aromatic, aliphatic, and cinnamic aldehydes, providing facile access to a variety of diazole derivatives bearing a 2-amino substituent in an efficient and scalable fashion.
• A direct link between the Passerini reaction and α-lactams
  作者：István Lengyel、Victor Cesare、Tony Taldone

  DOI：10.1016/j.tet.2003.11.067

  日期：2004.1

  α-Lactams (aziridinones) can function to replace two of the three reactants, the oxo-compound and the isonitrile, in the Passerini reaction. Four α-lactams (5a-d) were reacted with mono- and dicarboxylic acids of positive pKa values to give 2-acyloxycarboxamides (4) and bis-2-acyloxycarboxamide products 12 and 13, respectively. The same compounds were also prepared via the Passerini reaction. Acids

  α-内酰胺（叠氮ino烷）可以在Passerini反应中取代三种反应物中的两种，即氧代化合物和异腈。使四个α-内酰胺（5a - d）与正p K a值的单羧酸和二羧酸反应，分别得到2-酰氧基羧酰胺（4）和双-2-酰氧基羧酰胺产物12和13。还通过Passerini反应制备了相同的化合物。p K a p为负的酸将α-内酰胺脱羰，生成铵盐。反应的主要路径取决于p K a 酸成分，α-内酰胺的反应性和反应条件。