4-{bis[4-(trifluoromethyl)phenyl]hydroxymethyl}piperidine | 183994-24-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-{bis[4-(trifluoromethyl)phenyl]hydroxymethyl}piperidine
• 英文别名: 4-[bis(4-trifluoromethylphenyl)hydroxymethyl]piperidine；(4-Piperidinyl)bis[4-(trifluoromethyl)phenyl]methanol；piperidin-4-yl-bis[4-(trifluoromethyl)phenyl]methanol
• CAS: 183994-24-3
• 化学式: C₂₀H₁₉F₆NO
• 分子量: 403.367
• InChiKey: AHKZPCLXSIBVDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-{bis[4-(trifluoromethyl)phenyl]hydroxymethyl}piperidine 在 三氟乙酸 、 ice water 、 二氯甲烷 、 氯化钠 、 正己烷 作用下， 以 三氟乙酸 为溶剂， 反应 4.0h， 以yielding in two crops, 9.1 grams of the subject compound的产率得到4-{bis[4-(trifluoromethyl)phenyl]methylene}piperidine
  参考文献：
  名称：

  N-(substituted arylmethyl)-4-(disubstituted methyl) piperidines and pyridines

  摘要：

  现已发现某些新型N-(取代芳基)-4(二取代甲基)哌啶和吡啶衍生物具有出乎意料的杀虫活性。这些化合物由式(I)表示：其中m、n、q、r和s独立地选自0或1；p为0、1、2或3；A为C或CH；B、D、E、R、R1、R2、R3、R4、R5、R6、R7和R8在此完整描述。此外，还公开了包含式(I)中至少一种化合物的杀虫有效量和可选的第二种化合物的有效量，以及至少一种杀虫兼容载体的组合物；以及控制昆虫的方法，包括将所述组合物应用于昆虫存在或预计存在的地点。

  公开号：

  US20060135504A1
• 作为产物：
  描述：

  1-苄基-4-哌啶甲酸甲酯 在 正丁基锂 、 5%-palladium/activated carbon 、 氢气 作用下， 以 乙醚 、 乙醇 、 正己烷 为溶剂， 5.0~45.0 ℃ 、101.33 kPa 条件下， 反应 27.0h， 生成 4-{bis[4-(trifluoromethyl)phenyl]hydroxymethyl}piperidine
  参考文献：
  名称：

  新型赖氨酸甲基转移酶G9a小分子抑制剂的发现及其在白血病细胞系中的作用机制

  摘要：

  赖氨酸甲基转移酶G9a主要通过催化组蛋白H3赖氨酸9的单甲基和二甲基化以及几个非组蛋白赖氨酸位点来调节多个基因的转录。小鼠G9a基因敲除研究是治疗白血病的诱人治疗靶标，它已发现由于HoxA9依赖性转录的减弱，急性髓样白血病（AML）细胞的增殖和自我更新显着减慢。在这项研究中，通过基于结构的虚拟筛选将一系列化合物鉴定为潜在抑制剂。在这些化合物中，通过体外证实了一种新的G9a抑制剂DCG066生化和基于细胞的酶测定。与目前可获得的其他G9a抑制剂不同，DCG066具有新颖的分子支架。与G9a的组蛋白底物相似，DCG066可以直接与G9a结合并在体外抑制甲基转移酶的活性。除了抑制G9a甲基转移酶活性并降低组蛋白H3甲基化水平外，DCG066在具有高水平G9a表达的白血病细胞系（包括K562）中显示出低细胞毒性。这项工作提出了DCG066作为具有新型结构的G9a抑制剂，既提供了G9a抑制剂设计的先河，又提供了探测G9a功能的手段。

  DOI：

  10.1016/j.ejmech.2016.06.028

文献信息

• Insecticidal n-(substituted arylmethyl)-4-[bis(substituted phenyl) methyl]p
  申请人：FMC Corporation

  公开号：US05569664A1

  公开（公告）日：1996-10-29

  Compounds of the following structure, the corresponding N-oxides and agriculturally acceptable salts, are disclosed as effective insecticides: ##STR1## in which U is selected from ##STR2## Q is selected from hydrogen, hydroxy, sulfhydryl, and fluorine; R is selected from a heterocycle having 5 or 6 ring atoms, optionally fused to a benzene ring, and ##STR3## wherein V, W, X, Y, Z are as defined in the specification.

  以下结构化合物，对应的N-氧化物和农业可接受的盐，被披露为有效的杀虫剂：##STR1## 其中U从##STR2## 中选择，Q从氢、羟基、硫醇和氟中选择；R从具有5个或6个环原子的杂环中选择，可选地融合到苯环和##STR3## 中选择，其中V、W、X、Y、Z如规范中定义。
• Insecticidal N-(substituted arylmethyl)-4-[bis(substituted
  申请人：FMC Corporation

  公开号：US05639763A1

  公开（公告）日：1997-06-17

  Compounds of the following structure, the corresponding N-oxides and agriculturally acceptable salts, are disclosed as effective insecticides: ##STR1## in which U is selected from --(CH.sub.2).sub.n -- and ethylidene; Q is selected from hydrogen, hydroxy, sulfhydryl, and fluorine; R is ##STR2## in which V is selected from hydrogen, halogen, alkyl, haloalkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsilyloxy, dialkylamino, cyano, nitro, hydroxy, and phenyl; Y and Z are independently selected from hydrogen and alkoxy; W and X taken together is --OCH.sub.2 CH.sub.2 O--, --CH.sub.2 C(CH.sub.3).sub.2 O--, --OC(CH.sub.3).sub.2 O--, or --N.dbd.C(C.sub.2 H.sub.5)O--; R.sup.1 and R.sup.2 are independently selected from phenyl substituted with halogen, alkyl, haloalkyl, haloalkoxy, alkoxyalkyl, hydroxy, arylthio, alkoxy, dialkylamino, dialkylaminosulfonyl, hydroxyalkylaminocarbonyl, alkylsulfonyloxy, and haloalkylsulfonyloxy; and n is 1, 2, or 3.

  公开了具有以下结构的化合物，相应的N-氧化物和农业可接受的盐作为有效的杀虫剂：##STR1## 其中U从--(CH.sub.2).sub.n--和乙烯基中选择；Q从氢、羟基、硫醇和氟中选择；R从##STR2## 中选择，其中V从氢、卤素、烷基、卤代烷基、烷氧基、烷基硫基、烷基亚砜基、烷基硅氧基、二烷基氨基、氰基、硝基、羟基和苯基中选择；Y和Z独立地从氢和烷氧基中选择；W和X结合在一起是--OCH.sub.2 CH.sub.2 O--，--CH.sub.2 C(CH.sub.3).sub.2 O--，--OC(CH.sub.3).sub.2 O--或--N.dbd.C(C.sub.2 H.sub.5)O--；R.sup.1和R.sup.2独立地从用卤素、烷基、卤代烷基、卤代烷氧基、烷氧基烷基、羟基、芳基硫基、烷氧基、二烷基氨基、二烷基氨基磺酰基、羟基烷基氨基羰基、烷基砜氧基和卤代烷基砜氧基取代的苯基中选择；n为1、2或3。
• [EN] N-(SUBSTITUTED ARYLMETHYL)-4-(DISUBSTITUTED METHYL) PIPERIDINES AND PYRIDINES<br/>[FR] N-(ARYLMETHYL SUBSTITUE)-4-(METHYL DISUBSTITUE) PIPERIDINES ET PYRIDINES ASSOCIEES
  申请人：FMC CORP

  公开号：WO2004060371A1

  公开（公告）日：2004-07-22

  It has now been found that certain novel N-(substituted aryl)-4(disubstituted methyl)piperidine and pyridine derivatives have provided unexpected insecticidal activity. These compounds are represented by formula (I): wherein m, n, q, r, and s are independently selected fronn 0 or 1 ; and p is 0, 1, 2, or 3; A is C or CH; and B, D, E, R, R1, R2, R3, R4, R5, R6, R7 and R8 are fully described herein. In addition, compositions comprising an insecticidally effective amount of at least one compound of formula I, and optionally, an effective amount of at least one of a second compound, with at least one insecticidally compatible carrier are also disclosed; along with methods of controlling insects comprising applying said compositions to a locus where insects are present or are expected to be present.

  现在已经发现，某些新型的N-(取代芳基)-4(二取代甲基)哌啶和吡啶衍生物具有意想不到的杀虫活性。这些化合物由公式(I)表示：其中m、n、q、r和s分别独立地从0或1中选择；p为0、1、2或3；A为C或CH；B、D、E、R、R1、R2、R3、R4、R5、R6、R7和R8在此处均有完整描述。此外，还披露了包含公式I中至少一种化合物的杀虫有效量的组合物，以及可选地含有至少一种第二化合物的有效量，其中至少一种杀虫兼容载体；以及控制昆虫的方法，包括将上述组合物应用于昆虫存在或预计存在的地点。
• Insecticidal compositions containing n-(substituted
  申请人：FMC Corporation

  公开号：US06017931A1

  公开（公告）日：2000-01-25

  Compositions containing compounds of the following structure, some of which are novel, and the corresponding N-oxides and agriculturally acceptable salts, are disclosed as effective insecticides: ##STR1## in which U is --(CH.sub.2).sub.n --; Q is hydroxy; R is ##STR2## in which V, W, and Z are each hydrogen; X is selected from alkoxy, haloalkoxy, alkoxyalkyl, cycloalkylalkoxy, halocycloalkylalkoxy, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkylalkoxycarbonyl, halocycloalkylalkoxycarbonyl, alkoxyalkoxycarbonyl, alkoxycarbonylamino, haloalkoxycarbonylamino, cycloalkylalkoxycarbonylamino, halocycloalkylalkoxycarbonylamino, alkylaminocarbonyl, haloalkylaminocarbonyl, cyanoalkoxycarbonylamino, phenylcarbonylamino, and phenoxycarbonyl, each cycloalkyl moiety or phenyl ring optionally substituted with halogen; Y is selected from hydrogen and halogen; n is 1, 2, or 3; R.sup.1 and R.sup.2 are independently selected from phenyl or pyridyl, each substituted with haloalkyl, haloalkoxy, or alkylthio; with the proviso that each aliphatic moiety contains not more than 6 carbon atoms, and halogen means bromine, chlorine or fluorine.

  本发明涉及含有以下结构的化合物，其中一些是新颖的，以及对应的N-氧化物和农业可接受的盐，作为有效的杀虫剂：##STR1## 其中U为--(CH.sub.2).sub.n --; Q为羟基; R为##STR2## 其中V、W和Z均为氢; X选自烷氧基、卤代烷氧基、烷氧基烷基、环烷基烷氧基、卤代环烷基烷氧基、烷氧羰基、卤代烷氧羰基、环烷基烷氧羰基、卤代环烷基烷氧羰基、烷氧基烷氧羰基、烷氧羰基氨基、卤代烷氧羰基氨基、环烷基烷氧羰基氨基、卤代环烷基烷氧羰基氨基、烷基氨基羰基、卤代烷基氨基羰基、氰基烷氧羰基氨基、苯基羰基氨基和苯氧羰基，每个环烷基或苯环可选择地取代卤素; Y选自氢和卤素; n为1、2或3; R.sup.1和R.sup.2独立地选自取代有卤代烷基、卤代烷氧基或烷基硫的苯基或吡啶基，其中每个脂肪族基含有不超过6个碳原子，卤素表示溴、氯或氟。
• Insecticidal N-(substituted arylmethyl)-4-\x9bbis(substituted
  申请人：FMC Corporation

  公开号：US05795901A1

  公开（公告）日：1998-08-18

  Compounds of the following structure are disclosed as effective insecticides: ##STR1## in which Q is hydroxy; U is --(CH.sub.2).sub.n --, where n is 1; R is ##STR2## in which V, W, Y, and Z are each hydrogen; X is alkoxy, cycloalkylalkoxy, alkoxycarbonyl, alkoxycarbonylamino, or a five- or six-membered heteroaryl or heteroaryloxy, each heteroaryl optionally substituted with halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, or haloalkoxyalkyl; R.sup.1 and R.sup.2 are independently selected from haloalkyl; phenyl substituted with halogen, halothio, haloalkyl, or haloalkoxy; or a five- or six-membered heteroaryl substituted with halogen or haloalkyl; R.sup.3 is alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, dialkylaminoalkyl, alkylaminocarbonyloxyalkyl, alkylthioalkyl, alkylsulfonylalkyl, alkylcarbonyloxyalkyl, alkoxycarbonylalkyl, carboxyalkyl, carboxyarylalkyl, arylcarbonyl, sulfonato, or sulfonatoalkyl, and may bear a negative charge resulting in an inner salt; and a separate anion is chloride, bromide, iodide, or an phenyl or alkyl sulfate or sulfonate; with the proviso that at least one of R.sup.1 and R.sup.2 is phenyl substituted in the para position or pyrid-2-yl or pyrimidin-2-yl, each substituted in the the 5-position; each aliphatic moiety contains not more than 4 carbon atoms, except that R.sup.3 may contain up to eighteen carbon atoms; halogen means bromine, chlorine, or fluorine; each heteroaryl contains from 1 to 4 nitrogen atoms, or 1 or 2 oxygen or sulfur atoms, or 1 or 2 nitrogen atoms and an oxygen or sulfur atom.

  以下结构的化合物被披露为有效的杀虫剂：## STR1 ## 其中Q为羟基；U为-(CH2)n-，其中n为1；R为## STR2 ## 其中V、W、Y和Z均为氢；X为烷氧基、环烷基烷氧基、烷氧羰基、烷氧羰基氨基或含五元或六元杂环的杂环氧基，每个杂环可选地用卤素、氰基、烷基、卤代烷基、烷氧基、卤代烷氧基、烷氧基烷基或卤代烷氧基烷基取代；R1和R2分别选自卤代烷基；用卤素、卤硫、卤代烷基或卤代烷氧基取代的苯基；或用卤代烷基取代的含五元或六元杂环；R3为烷基、卤代烷基、羟基烷基、烷氧基烷基、二烷基氨基烷基、烷基氨基羰酰氧烷基、烷基硫基烷基、烷基磺酰基烷基、烷基羰酰氧烷基、烷氧羰基烷基、羧基烷基、芳基羧基、磺酸盐或磺酸盐烷基，并且可能带有负电荷形成内盐；另外还有一个阴离子，可以是氯离子、溴离子、碘离子或苯基或烷基硫酸盐或磺酸盐；但至少有一个R1和R2是用卤代苯基在对位或用吡啶-2-基或嘧啶-2-基在5位取代的；每个脂肪族基团含不超过4个碳原子，除了R3可以含有多达18个碳原子；卤素表示溴、氯或氟；每个杂环含有1至4个氮原子，或1或2个氧或硫原子，或1或2个氮原子和1个氧或硫原子。