cyclohexanone diphenylhydrazone | 19691-06-6

• 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: cyclohexanone diphenylhydrazone
• 英文别名: Cyclohexanon-(N,N-diphenyl)-hydrazon；Cyclohexanon-diphenylhydrazon；cyclohexanone N,N-diphenylhydrazone；N-(cyclohexylideneamino)-N-phenylaniline
• CAS: 19691-06-6
• 化学式: C₁₈H₂₀N₂
• 分子量: 264.37
• InChiKey: OXRIWAUMTZABNQ-UHFFFAOYSA-N

物化性质

• 熔点：
  71 °C
• 沸点：
  398.7±25.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲基丙二酸 、 cyclohexanone diphenylhydrazone 在 乙酸酐 作用下， 反应 0.08h， 生成 5-diphenylamino-3-methyl-1-oxa-5-aza-spiro[5.5]undecane-2,4-dione
  参考文献：
  名称：

  Synthesen von Heterocyclen, 113. Mitt.: �ber Reaktionen von Ketonhydrazonen mit Malons�urederivaten

  摘要：

  DOI：

  10.1007/bf00902692
• 作为产物：
  描述：

  1,1-二苯肼盐酸盐 、 环己酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 cyclohexanone diphenylhydrazone
  参考文献：
  名称：

  Synthesis of .beta.-lactams via cycloaddition of hydrazones with phenoxyketene

  摘要：

  DOI：

  10.1021/jo00294a040

文献信息

• One-Pot Synthesis of Indoles from Ketones and Hydrazines under Mild Reaction Conditions
  作者：Okiko Miyata、Yasuo Kimura、Takeaki Naito

  DOI：10.1055/s-2001-16756

  日期：——

  A facile one-pot method is presented for the synthesis of indoles via condensation of ketone with hydrazine followed by acylation and rearrangement. This convenient synthetic method provides an easy and simple access to indoles.

  本文介绍了一种简便的一锅法合成吲哚方法，通过酮与肼的缩合反应，随后进行酰化及重排。这种方法方便快捷，为合成吲哚提供了一种简单易行的途径。
• Efficient synthesis of indoles using [3,3]-sigmatropic rearrangement of N-trifluoroacetyl enehydrazines
  作者：Okiko Miyata、Norihiko Takeda、Yasuo Kimura、Yoshiji Takemoto、Norimitsu Tohnai、Mikiji Miyata、Takeaki Naito

  DOI：10.1016/j.tet.2006.01.087

  日期：2006.4

  [3,3]-Sigmatropic rearrangement of N-triflluoroacetyl enehydrazines provides a novel method for the construction of indoles. N-Trifluoroacetyl enehydrazine having a cyclopentene ring smoothly underwent [3,3]-sign-tatropic rearrangement followed by cyclization to give indolines in excellent yield. On the other hand, both cyclohexenyl N-trifluoroacetyl enchydrazine and acyclic N-trifluoroacetyl enehydrazine gave indoles in good yield. Additionally, the substituent effect on the benzene ring was also studied. The rearrangement of N-trifluoroacetyl enchydrazines proceeded smoothly even Linder either aqueous or solvent-free conditions. (c) 2006 Elsevier Ltd. All rights reserved.
• Goerdeler,J.; Bischoff,M., Chemische Berichte, 1972, vol. 105, p. 3566 - 3573
  作者：Goerdeler,J.、Bischoff,M.

  DOI：——

  日期：——
• Orthomanganation of arylhydrazones and related N-donor substrates
  作者：Maarten B. Dinger、Lyndsay Main、Brian K. Nicholson

  DOI：10.1016/s0022-328x(98)00453-7

  日期：1998.8

  The N-phenyl- and N,N-diphenylhydrazones of benzaldehyde or acetophenone are readily cyclometallated on reaction with PhCH2Mn(CO)(5) to give complexes 3 of the type (OC)(4)MnC6H4C(R-1)=NNPhR2 incorporating a five-membered MnC3N ring. The example with R-1 = Me, R-2 = H has been structurally characterised. The similar reaction with the N,N-diphenylhydrazone of cyclohexanone produces a species with an alternative MnC2N2 ring which was also structurally characterised. A related species (OC)(4)MnC6H4NN=O is formed from N-nitrosodiphenylamine. Reactions of compounds 3 from the diphenylhydrazones with alkynes PhC=CPh or Me3SiC=CH give N'-indenyl-N,N-diphenylhydrazines in reasonable yields. (C) 1998 Elsevier Science S.A. All rights reserved.
• SHARMA, S. D.;PANDHI, S. B., J. ORG. CHEM., 55,(1990) N, C. 2196-2200
  作者：SHARMA, S. D.、PANDHI, S. B.

  DOI：——

  日期：——