2-methylcyclohex-2-en-1-one E-oxime | 51552-21-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-methylcyclohex-2-en-1-one E-oxime
• 英文别名: (E)-2-methylcyclohex-2-enone oxime；E-2-methyl-2-cyclohexenone oxime；2-Methylcyclohex-2-enonoxim；(NE)-N-(2-methylcyclohex-2-en-1-ylidene)hydroxylamine
• CAS: 51552-21-7
• 化学式: C₇H₁₁NO
• 分子量: 125.17
• InChiKey: IOWQGZJAPAFKSL-BQYQJAHWSA-N

物化性质

• 熔点：
  64-65 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  235.0±23.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methylcyclohex-2-en-1-one E-oxime 以19%的产率得到
  参考文献：
  名称：

  GIRAULT, Y.;DECOUZON, M.;AZZARO, M., TETRAHEDRON LETT., 1984, 25, N 26, 2763-2766

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基-2-环己烯-1-酮 在 盐酸羟胺 、 sodium acetate 作用下， 以 甲醇 、 水 为溶剂， 反应 0.08h， 以51%的产率得到2-methylcyclohex-2-en-1-one E-oxime
  参考文献：
  名称：

  Oximes: Metabolic Activation and Structure−Allergenic Activity Relationships

  摘要：

  Metabolic activation of chemicals (prohaptens) in the skin can cause allergic contact dermatitis. We have explored structure -allergenic activity relationships for seven potential oxime prohaptens using the local lymph node assay and a GSH trapping screen with liver microsomes. The general structure -allergenic activity relationships found were that an (alpha,beta-unsaturation is necessary for an oxime to be a prohapten and that increased steric hindrance around this double bond leads to reduction in sensitizing capacity. We also found that sensitizing oximes can be distinguished in vitro from nonsensitizers by monitoring of monooxidized (+16 Da) GSH conjugates in the GSH trapping screen. However, care should be taken when interpreting data from GSH trapping screens, as nonsensitizers may also form GSH conjugates via alternative mechanisms. This investigation emphasizes the importance of considering cutaneous bioactivation in toxicity assessment of chemicals used in contact with the skin.

  DOI：

  10.1021/jm701092n

文献信息

• Tashchi, V. P.; Rukasov, A. F.; Orlova, T. I., Journal of Organic Chemistry USSR (English Translation), 1984, p. 899 - 907
  作者：Tashchi, V. P.、Rukasov, A. F.、Orlova, T. I.、Ivanov, A. P.、Tashchi, O. A.、et al.

  DOI：——

  日期：——
• ——
  作者：A. M. Chibiryaev、A. Yu. Denisov、D. V. Pyshnyi、A. V. Tkachev

  DOI：10.1023/a:1012785007135

  日期：——

  Using a number of cyclic alpha,beta-unsaturated oximes of the terpene series and sonic Simplest model compounds as examples, unsaturated oximes bearing a hydrogen atom it the beta-carbon atom were demonstrated to be converted into beta-hydroxyiminonitroalkenes under the action of sodium nitrite and acetic acid in methanol. In the case of the introduction of an alkyl substituent at the terminal carbon atom of the diene C=C-C=NOH fragment, the reaction performed under the same conditions gave rise exclusively to conjugated ketone (a deoximation product).
• Zaidlewicz, Marek; Uzarewicz, Ireneusz G., Polish Journal of Chemistry, 1988, vol. 62, # 1-3, p. 143 - 150
  作者：Zaidlewicz, Marek、Uzarewicz, Ireneusz G.

  DOI：——

  日期：——
• Synthese d'aziridines N-non substituees par reduction de sels d'hydrazonium
  作者：Yvonne Girault、Michèle Decouzon、Marcel Azzaro

  DOI：10.1016/s0040-4039(01)81284-3

  日期：——
• ZAIDLEWICZ, MAREK;UZAREWICZ, IRENEUSZ G., POL. J. CHEM., 62,(1988) N-3, C. 143-150
  作者：ZAIDLEWICZ, MAREK、UZAREWICZ, IRENEUSZ G.

  DOI：——

  日期：——