3-Methoxy-4-oxo-α-phenyl-cyclohexadien-(2,5)-Δ^1,α-acetonitril-oxim | 842-49-9

• 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: 3-Methoxy-4-oxo-α-phenyl-cyclohexadien-(2,5)-Δ^1,α-acetonitril-oxim
• 英文别名: 2-Methoxy-4-<α-cyan-benzyliden>-2,5-cyclohexadien-1-on-oxim；2-Methoxy-4-(α-cyan-benzyliden)-2,5-cyclohexadien-1-on-oxim；(4-Hydroxyimino-3-methoxy-cyclohexa-2,5-dienylidene)-phenylacetonitrile；2-(4-hydroxyimino-3-methoxycyclohexa-2,5-dien-1-ylidene)-2-phenylacetonitrile
• CAS: 842-49-9
• 化学式: C₁₅H₁₂N₂O₂
• 分子量: 252.272
• InChiKey: YBKTXKZDUUDTKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  65.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-硝基苯甲醚 、 苯乙腈 以 水 为溶剂， 反应 0.67h， 以86%的产率得到3-Methoxy-4-oxo-α-phenyl-cyclohexadien-(2,5)-Δ^1,α-acetonitril-oxim
  参考文献：
  名称：

  从苯基乙腈和4-未取代的硝基芳香化合物arylcyanomethylenequinone肟的无溶剂机械化学合成使用KF /纳米的γ-Al 2 ö 3作为催化剂†

  摘要：

  与4-未取代的硝基芳香化合物苯基乙腈的无溶剂缩合，以产生一系列arylcyanomethylenequinone肟在KF /存在纳米γ-A1中描述的2 ö 3高速振动研磨条件下，并且在中等，获得的产品在短的反应时间内达到优异的收率。另外，通过X射线衍射分析确认了产物α-（3-甲基-4-（羟基亚氨基）-2，5-环己二烯-1-亚烷基）苯乙腈3b。在不同温度下，在丙酮-d 6中通过1 H NMR测定了由肟形成的亚硝基异构体。体外 抗肿瘤研究表明，几种芳基氰基亚甲基醌肟对Caki-1和769-P具有很强的抗肿瘤活性。

  DOI：

  10.1039/c5ra23606a

文献信息

• Oxime sulfonates and the use thereof as latent sulfonic acids
  申请人：Ciba Specialty Chemicals Corporation

  公开号：US06004724A1

  公开（公告）日：1999-12-21

  New oximsulfonate compounds of the formulae I or II, ##STR1## wherein m is 0 or 1; x is 1 or 2; R.sub.1 is, for example phenyl, which is unsubstituted or substituted or R.sub.1 is a heteroaryl radical that is unsubstituted or substituted, or, if m is 0, R.sub.1 additionally is C.sub.2 -C.sub.6 alkoxycarbonyl, phenoxycarbonyl or CN; R'.sub.1 is for example C.sub.2 -C.sub.12 alkylene, phenylene; R.sub.2 has for example one of the meanings of R.sub.1 ; n is 1 or 2; R.sub.3 is for example C.sub.1 -C.sub.18 alkyl, R'.sub.3 when x is 1, has one of the meanings given for R.sub.3, or R'.sub.3 in the formula IV and when x is 2 in the formula 1, is for example C.sub.2 -C.sub.12 alkylene, phenylene; R.sub.4 and R.sub.5 are independently of each other for example hydrogen, halogen, C.sub.1 -C.sub.6 alkyl; R.sub.6 is for example hydrogen, phenyl; R.sub.7 and R.sub.8 are independently of each other for example hydrogen or C.sub.1 -C.sub.12 -alkyl; R.sub.9 is for example C.sub.1 -C.sub.12 alkyl; A is S, O, NR.sub.6, or a group of formula A1, A2, A3 or A4 ##STR2## R.sub.10 and R.sub.11 independently of each other have one of the meanings given for R.sub.4 ; R.sub.12, R.sub.13, R.sub.14 and R.sub.15 independently of one another are for example hydrogen, C.sub.1 -C.sub.4 alkyl; Z is CR.sub.11 or N; Z.sub.1 is --CH.sub.2 --, S, O or NR.sub.6, are useful as latent sulfonic acids, especially in photoresist applications.

  式I或II的新的氧磺酸盐化合物，其中m为0或1；x为1或2；R.sub.1是例如苯基，未取代或取代，或R.sub.1是未取代或取代的杂环基基团，或者如果m为0，则R.sub.1还是C.sub.2-C.sub.6烷氧羰基，苯氧羰基或CN；R'.sub.1例如是C.sub.2-C.sub.12烷基，苯基；R.sub.2例如具有R.sub.1的一种含义；n为1或2；R.sub.3例如是C.sub.1-C.sub.18烷基，当x为1时，R'.sub.3具有为R.sub.3给出的含义之一，或者当x为2时，在式1中的公式IV中，R'.sub.3例如是C.sub.2-C.sub.12烷基，苯基；R.sub.4和R.sub.5独立地例如是氢，卤素，C.sub.1-C.sub.6烷基；R.sub.6例如是氢，苯基；R.sub.7和R.sub.8独立地例如是氢或C.sub.1-C.sub.12烷基；R.sub.9例如是C.sub.1-C.sub.12烷基；A是S，O，NR.sub.6或者是式A1，A2，A3或A4的基团，其中R.sub.10和R.sub.11独立地具有R.sub.4给出的含义之一；R.sub.12，R.sub.13，R.sub.14和R.sub.15独立地例如是氢，C.sub.1-C.sub.4烷基；Z为CR.sub.11或N；Z.sub.1为--CH.sub.2--，S，O或NR.sub.6。这些化合物作为潜在的磺酸盐，特别是在光刻应用中。
• Solvent-free mechanochemical synthesis of arylcyanomethylenequinone oximes from phenylacetonitriles and 4-unsubstituted nitroaromatic compounds using KF/nano-γ-Al₂O₃ as catalyst
  作者：Zhi Hong、Jian-Jun Li、Guang Chen、Hua-Jiang Jiang、Xiao-Feng Yang、Heng Pan、Wei-Ke Su

  DOI：10.1039/c5ra23606a

  日期：——

  Solvent-free condensation of phenylacetonitriles with 4-unsubstituted nitroaromatic compounds to produce a series of arylcyanomethylenequinone oximes was described in the presence of KF/nano-γ-Al2O3 under high-speed vibration milling conditions, and the products were obtained in moderate to excellent yields at short reaction times. Moreover, the product α-(3-methyl-4-(hydroxyimino)-2,5-cyclohexadien-1-ylidene)

  与4-未取代的硝基芳香化合物苯基乙腈的无溶剂缩合，以产生一系列arylcyanomethylenequinone肟在KF /存在纳米γ-A1中描述的2 ö 3高速振动研磨条件下，并且在中等，获得的产品在短的反应时间内达到优异的收率。另外，通过X射线衍射分析确认了产物α-（3-甲基-4-（羟基亚氨基）-2，5-环己二烯-1-亚烷基）苯乙腈3b。在不同温度下，在丙酮-d 6中通过1 H NMR测定了由肟形成的亚硝基异构体。体外 抗肿瘤研究表明，几种芳基氰基亚甲基醌肟对Caki-1和769-P具有很强的抗肿瘤活性。