4-二氯甲基-4-甲基-2,5-环己烷二酮 | 6611-78-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-二氯甲基-4-甲基-2,5-环己烷二酮
• 英文名称: 4-dichloromethyl-4-methyl-2,5-cyclohexadienone
• 英文别名: 4-(dichloromethyl)-4-methylcyclohexa-2,5-dien-1-one；4-dichloromethyl-4-methylcyclohexa-2,5-dien-1-one；4-methyl-4-dichloromethyl-2,5-cyclohexadien-1-one；4-dichloromethyl-4-methyl-cyclohexa-2,5-dienone；4-Dichlormethyl-4-methyl-cyclohexa-2,5-dienon；1¹.1¹-Dichlor-1.1-dimethyl-cyclohexadien-(2.5)-on-(4)
• CAS: 6611-78-5
• 化学式: C₈H₈Cl₂O
• mdl: MFCD00019435
• 分子量: 191.057
• InChiKey: MJRRCEHODULPAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-二氯甲基-4-甲基-2,5-环己烷二酮 在 chromium(III) oxide 、 乙醚 、 乙醇 、 硫酸 、 sodium 、 钯 作用下， 生成 4,4-二甲基环己酮
  参考文献：
  名称：

  v. Auwers; Lange, Justus Liebigs Annalen der Chemie, 1913, vol. 401, p. 313

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲基-4-(三氯甲基)环己-2,5-二烯-1-酮 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 4-二氯甲基-4-甲基-2,5-环己烷二酮
  参考文献：
  名称：

  Electrochemical reduction of 4-methyl-4-(trichloromethyl)cyclohexa-2,5-dien-1-one

  摘要：

  DOI：

  10.1134/s1070363214060036

文献信息

• Toluene as a novel carrier of xanthates—preparation, use and surrogate of S-tri- and di-chloromethyl xanthates
  作者：Raphaël Dumeunier、Annika Huber

  DOI：10.1016/j.tetlet.2014.06.030

  日期：2014.7

  Toluene has been identified as a novel carrier of xanthates. Their corresponding fragmentative precursors proved to behave efficiently in radical group transfer reactions. As examples, unprecedented S-tri/di-chloromethyl xanthates could be prepared, isolated and further used in radical additions to olefins. Their precursors (de-aromatized toluene upon which is grafted, at one end, a tri/di-chloromethyl-group

  甲苯已被确定为黄药的新型载体。事实证明，它们相应的片段化前体在自由基基团转移反应中可有效发挥作用。作为实例，可以制备，分离和进一步用于烯烃的自由基加成中空前的S-三/二氯甲基黄原酸酯。它们的前体（去芳香化的甲苯，其一端接有三/二氯甲基，而另一端接有二硫代羰基）也可直接用于两个基团向烯烃的转移。因此，通过前体的自由基引发的断裂而重新芳香化损失的甲苯给黄原酸酯的化学带来了新的机会，在此以新的S -tri /二氯甲基黄原酸酯的分子间加成为例。
• Electrochemically induced transformation of 4(6)-dihalomethyl-4(6)-methylcyclohexa-2,5(2,4)-dien-1-ones into 4(2)-methyltropones
  作者：A. A. Moiseeva、G. V. Gavrilova、E. K. Beloglazkina、D. M. Krut’ko、N. V. Zyk

  DOI：10.1134/s1070363211080135

  日期：2011.8

  Electrochemical investigation of 4(6)-dihalomethyl-4(6)-methylcyclohexa-2,5(2,4)-dien-1-ones using cyclic voltammetry (CVA) and rotating disc electrode (RDE) methods has been performed. The reductive dehalogenation of cyclohexa-2,5(2,4)-dien-1-ones having a dihalomethyl substituent at the tertiary carbon atom was shown to proceed as a two-electron reductive elimination of the geminal halogen atoms

  使用循环伏安法（CVA）和旋转盘电极（RDE）方法对4（6）-二卤甲基-4（6）-甲基环己-2,5（2,4）-二烯-1-酮进行了电化学研究。显示在叔碳原子上具有二卤甲基取代基的环己2,5（2,4）-二烯-1-酮的还原脱卤反应是通过双电子还原消除双键卤素原子而中间形成的卡宾和随后的环己二烯酮的重排，其环扩展为相应的4-或2-甲基环庚-2,4,6-三烯-1-酮。
• Process for selectively producing para-substituted derivatives of phenols
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：US04523037A1

  公开（公告）日：1985-06-11

  By reacting, using as a catalyst a modified or unmodified cyclodextrin, a phenol compound with a haloform in the presence of an alkali metal hydroxide, while maintaining the molar ratio of the cyclodextrin to the haloform at 0.5 to 10, a substituent group derived from the haloform can be introduced to the para-position of the phenol compound with high selectivity, whereby useful para-substituted phenol derivatives can be advantageously obtained.

  通过在碱性金属氢氧化物存在的情况下，以改性或未改性的环糊精为催化剂，将含有卤仿的酚类化合物反应，同时保持环糊精与卤仿的摩尔比在0.5至10之间，可以高度选择性地将卤仿衍生的取代基引入到酚类化合物的对位，从而有利地获得有用的对位取代酚衍生物。
• Dialkyl-substituted dithianes and pesticidal compositions
  申请人：The Wellcome Foundation Ltd.

  公开号：US04985411A1

  公开（公告）日：1991-01-15

  The present invention provides compounds of the formula (I): ##STR1## wherein m and n are independently selected from 0, 1 or 2, ##STR2## R is selected from hydrogen, methyl or ethyl; R.sup.1 is selected from C.sub.1-4 hydrocarbyl substituted by one to five halo atoms, and a group --C.tbd.C--R.sup.9 wherein R.sup.9 is a group S(O).sub.w --R.sup.10 wherein R.sup.10 is trifluoromethyl, methyl or ethyl and w is 0, 1 or 2 or R.sup.9 is a C.sub.3-5 aliphatic group or an aliphatic group containing up to 5 carbon atoms atoms substituted by C.sub.1-4 alkoxy, C.sub.2-6 alkoxyalkoxy, C.sub.1-8 acyloxy, halo or hydroxy, a group COR.sup.11 wherein R.sup.11 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or a group NR.sup.12 R.sup.13 wherein R.sup.12 and R.sup.13 are independently selected from hydrogen, methyl or ethyl, or R.sup.9 is SiR.sup.14 R.sup.15 R.sup.16 wherein R.sup.14 to R.sup.16 are the same or different and each is a C.sub.1-4 aliphatic group or R.sup.14 and R.sup.15 are C.sub.1-4 aliphatic groups and R.sup.16 is a phenyl group; R.sup.2, R.sup.3, R.sup.7 and R.sup.8 are independently selected from hydrogen, methyl or halo; R.sup.4a and R.sup.4b, R.sup.6a and R.sup.6b are independently selected from hydrogen, C.sub.1-3 alkyl, C.sub.2-3 alkenyl or alkynyl each being optionally substituted by halo, cyano or C.sub.1-4 alkoxy; cyano, halo or a group COR .sup.11a wherein R.sup.11a is hydrogen, C.sub.1-4 alkoxy, C.sub.1-4 alkyl or a group NR.sup.12a R.sup.13a wherein R.sup.12a and R.sup.13a are independently selected from hydrogen, methyl or ethyl; R.sup.5a is a non-aromatic hydrocarbyl group containing up to seven carbon atoms, or phenyl each optionally substituted by cyano, halo, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.3-4 cycloalkyl, C.sub.1-4 alkoxy or a group S(O).sub.q R.sup.17 wherein q is 0, 1 or 2 and R.sup.17 is methyl or ethyl and R.sup.5b is hydrogen, hydroxy or C.sub.1-4 alkyl optionally substituted by alkoxy; and represents --CH--CH-- or --C.dbd.C-- which are useful pesticides, processes for their preparation, pesticidal formulations containing them and their use in the control or prevention of pest infestation.

  本发明提供了以下式（I）的化合物：其中m和n分别选择自0、1或2，R选择自氢、甲基或乙基；R.sup.1选择自C.sub.1-4烃基，被1至5个卤素原子取代，和一个--C.tbd.C--R.sup.9基团，其中R.sup.9是一个S(O).sub.w --R.sup.10基团，其中R.sup.10是三氟甲基、甲基或乙基，w为0、1或2，或者R.sup.9是一个C.sub.3-5脂肪基或含有多达5个碳原子的脂肪基，被C.sub.1-4烷氧基、C.sub.2-6烷氧基、C.sub.1-8酰氧基、卤素或羟基取代，一个COR.sup.11基团，其中R.sup.11是氢、C.sub.1-4烷基、C.sub.1-4烷氧基或一个NR.sup.12 R.sup.13基团，其中R.sup.12和R.sup.13分别选择自氢、甲基或乙基，或者R.sup.9是SiR.sup.14 R.sup.15 R.sup.16，其中R.sup.14到R.sup.16相同或不同，每个是一个C.sub.1-4脂肪基或R.sup.14和R.sup.15是C.sub.1-4脂肪基，R.sup.16是苯基；R.sup.2、R.sup.3、R.sup.7和R.sup.8分别选择自氢、甲基或卤素；R.sup.4a和R.sup.4b、R.sup.6a和R.sup.6b分别选择自氢、C.sub.1-3烷基、C.sub.2-3烯基或炔基，可以选择地被卤素、氰基或C.sub.1-4烷氧基取代；氰基、卤素或一个COR .sup.11a基团，其中R.sup.11a是氢、C.sub.1-4烷氧基、C.sub.1-4烷基或一个NR.sup.12a R.sup.13a基团，其中R.sup.12a和R.sup.13a分别选择自氢、甲基或乙基；R.sup.5a是一个非芳香烃基，含有多达七个碳原子，或苯基，可以选择地被氰基、卤素、C.sub.1-4烷基、C.sub.1-4卤代烷基、C.sub.3-4环烷基、C.sub.1-4烷氧基或一个S(O).sub.q R.sup.17基团取代，其中q为0、1或2，R.sup.17是甲基或乙基，R.sup.5b是氢、羟基或可选择地被烷氧基取代的C.sub.1-4烷基；代表--CH--CH--或--C.dbd.C--，它们是有用的杀虫剂，其制备方法，含有它们的杀虫剂配方以及其在控制或预防害虫侵害中的应用。
• Stereospecific acetoxylation of 4-methyl-4-dichloromethyl-5-(methoxycarbonyl)methyl-2-cyclohexen-1-one with lead(IV) acetate
  作者：Slavica Solujić、Slobodan Sukdolak、Zoran Ratković

  DOI：10.1016/0040-4039(91)80043-6

  日期：1991.1

  Acetoxylation of 4-methyl-4-dichloromethyl-5-(methoxycarbonyl)methyl-2--cyclohexen-1-one1 with lead(IV) acetate in the presence of Lewis acids gives the corresponding 6--α-acetoxylated derivative which, in an excess of boron trifluoride etherate (or in acidic media), undergoes cyclization to a -γ-lactone.

  的4-甲基-4-二氯甲基-5-（甲氧基羰基）甲基-2-乙酰氧基-环己烯-1-酮1在刘易斯的存在下用四乙酸铅的酸，得到相应的6- -α-乙酰氧基化衍生物，其，在过量的三氟化硼醚化物中（或在酸性介质中）进行环化成-γ-内酯。

表征谱图