N'-Cyclohexylidene-phosphorohydrazidic acid diethyl ester | 106537-24-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: N'-Cyclohexylidene-phosphorohydrazidic acid diethyl ester
• 英文别名: (diethoxyphosphorylhydrazinylidene)cyclohexane
• CAS: 106537-24-0
• 化学式: C₁₀H₂₁N₂O₃P
• 分子量: 248.262
• InChiKey: HWMNNVLHRKAPCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  59.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N'-Cyclohexylidene-phosphorohydrazidic acid diethyl ester 、 1,4-环己二酮 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Oligo(cyclohexylidenes): Parent Compounds and End-Functionalized Derivatives

  摘要：

  Parent oligo(cyclohexylidenes) 1(n) (n = 1-4) were synthesized using a modified Barton-Kellogg olefin synthesis. Surprisingly, the crude compounds 1(2) and 1(4) contained small amounts of the 1(n-1) and 1(n+1) homologues. As evidenced by a close examination of mass spectral data of selectively deuterated tercyclohexylidenes 1(2)d(4)d(4) and 1(2)-d(8), their formation can be attributed to scrambling of the intermediate azines. With increasing n, a marked decrease in solubility as well as an increase in thermal stability was found. Powder diffraction measurements indicate that the parent compounds 1(n), irrespective of n, pack in a similar fashion in the solid state. The theoretically (MMX, AM1, and ab initio) predicted rodlike structure of the oligo(cyclohexylidenes) was confirmed by single-crystal X-ray structures of 1(1) and three derivatives (12(1), 13(1), and 30(2)). In line with the powder diffraction data in the series 1(n), a similar packing motif was found for the derivatives. To circumvent side product formation due to azine scrambling, a different synthetic approach was used for the preparation of end-functionalized oligo(cyclohexylidenes), i.e. decarboxylation and dehydration of beta-hydroxy acids.

  DOI：

  10.1021/jo00119a014
• 作为产物：
  描述：

  phosphorohydrazidic acid diethyl ester 、 环己酮 以 苯 为溶剂， 反应 4.0h， 以80%的产率得到N'-Cyclohexylidene-phosphorohydrazidic acid diethyl ester
  参考文献：
  名称：

  A General Synthesis of Unsymmetrical Azines viaN-(Diethoxyphosphinyl)-hydrazones

  摘要：

  本论文介绍了一种利用磷酰肼二乙酯作为起始原料，并基于 Wadsworth-Emmons 型磷酰胺方法合成不对称叠氮的新方法。

  DOI：

  10.1055/s-1986-31589

文献信息

• KOZIARA, A.;TURSKI, K.;ZWIERZAK, A., SYNTHESIS, BRD, 1986, N 4, 298-301
  作者：KOZIARA, A.、TURSKI, K.、ZWIERZAK, A.

  DOI：——

  日期：——