5-氨基-4-氰基(1-2,4,6-三氯苯甲基)吡唑 | 79002-96-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氨基-4-氰基(1-2,4,6-三氯苯甲基)吡唑
• 中文别名: 5-氨基-1-(2,4,6-三氯苯基)-1H-吡唑-4-甲腈
• 英文名称: 5-amino-1-(2,4,6-trichlorophenyl)-1H-pyrazole-4-carbonitrile
• 英文别名: 5-amino-4-cyano-1-(2,4,6-trichlorophenyl)pyrazole；5-amino-1-(2,4,6-trichlorophenyl)pyrazole-4-carbonitrile
• CAS: 79002-96-3
• 化学式: C₁₀H₅Cl₃N₄
• 分子量: 287.535
• InChiKey: XLVSDPGXTLGTAE-UHFFFAOYSA-N

物化性质

• 熔点：
  187-195°C
• 沸点：
  187 °C
• 稳定性/保质期：
  远离氧化物、光、热和酸。

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 储存条件：
  存放在密封容器内，并放置在阴凉、干燥处。请将储存地点远离氧化剂，并在避光条件下于室温下保存。

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(+/-)-4-cyano-5-(4-methyl-2-oxo-azetidin-1-yl)-1-(2,4,6-trichlorophenyl)pyrazole	90630-01-6	C14H9Cl3N4O	355.611

反应信息

• 作为反应物：
  描述：

  5-氨基-4-氰基(1-2,4,6-三氯苯甲基)吡唑 在 硫酸 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 18.5h， 生成 6-methyl-1-(2,4,6-trichloro-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 1-Aryl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-4-one Inhibitors of Cyclin-Dependent Kinases

  摘要：

  Using a high-throughput screening strategy, a series of 1-aryl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-4-ones was identified that inhibit the cyclin-dependent kinase (CDK) 4/cyclin D1 complex-mediated phosphorylation of a protein substrate with IC(50)s in the low micromolar range. On the basis of preliminary structure-activity relationships (SAR), a model was proposed in which these inhibitors occupy the ATP-binding site of the enzyme, forming critical hydrogen bonds to the same residue (Val96) to which the amino group in ATP is presumed to bind. X-ray diffraction studies on a later derivative bound to CDK2 support this binding mode. Iterative cycles of synthesis and screening lead to a novel series of potent, CDK2-selective 6-(arylmethyl)pyrazolopyrimidinones. Placement of a hydrogen-bond donor in the meta-position on the 6-arylmethyl group resulted in approximately 100-fold increases in CDK4 affinity, giving ligands that were equipotent inhibitors of CDK4 and CDK2. These compounds exhibit antiproliferative effects in the NCI HCT116 and other cell lines. The potency of these antiproliferative effects is enhanced in anilide derivatives and translates into tumor growth inhibition in a mouse xenograft model.

  DOI：

  10.1021/jm020455u
• 作为产物：
  描述：

  乙氧基亚甲基丙二腈 生成 5-氨基-4-氰基(1-2,4,6-三氯苯甲基)吡唑
  参考文献：
  名称：

  Pyrazolopyrimidines as CRF antagonists

  摘要：

  以下为该化合物的中文翻译及其药用酸盐： 该化合物的化学式为：其中A为NR1R2、CR1R2R11、或C(═CR1R12)R2、NHCR1R2R11、OCR1R2R11、SCR1R2R11、NHNR1R2、CR2R11NHR1、CR2R11OR1、CR2R11SR1或C(O)R2；其中其余变量定义如下，用于治疗炎症性疾病。

  公开号：

  US06218397B1

文献信息

• A Facile One-pot Synthesis of 1-Arylpyrazolo[3,4-d]Pyrimidin- 4-ones
  作者：Xiaohong Zhang、Qiulian Lin、Ping Zhong

  DOI：10.3390/molecules15053079

  日期：——

  One pot synthesis of 1-arylpyrazolo[3,4-d]pyrimidin-4-ones by the reaction of 5-amino-N-substituted-1H-pyrazole-4-carbonitrile with different lower aliphatic acids in the presence of POCl3has been developed. The structures of all the title compounds have been confirmed by IR, 1H-NMR, 13C-NMR, and elemental analyses. Moreover, the structures of one of these compounds, 2c, was confirmed by single-crystal X-ray diffraction.

  一锅法合成1-芳基吡唑并[3,4-d]嘧啶-4-酮类化合物，通过5-氨基-N-取代-1H-吡唑-4-氰与不同低级脂肪酸在POCl3存在下的反应实现。所有目标化合物的结构已通过IR、1H-NMR、13C-NMR及元素分析确认。此外，其中一种化合物2c的结构还通过单晶X射线衍射进一步确认。
• 5-Acylamino-4-cyano-1-phenylpyrazole derivatives and use as herbicides
  申请人：May & Baker Limited

  公开号：US04459150A1

  公开（公告）日：1984-07-10

  New acylamino-N-phenylpyrazole derivatives of the formula: ##STR1## [wherein R.sup.1 represents R.sup.8 C(.dbd.O)--(wherein R.sup.8 represents H, C.sub.1-7 alkyl or C.sub.1-4 alkoxy optionally substituted by C.sub.1-4 alkoxy, C.sub.2-5 alkoxycarbonyl or halogen, C.sub.3-4 alkenyloxy, C.sub.3-6 cycloalkyl optionally substituted by CH.sub.3 or C.sub.2 H.sub.5, or phenoxy, R.sup.2 represents H or R.sup.8 C(.dbd.O)--, or R.sup.1 and R.sup.2 together represent --CO--(CR.sup.a R.sup.b).sub.m --CO--, R.sup.3 represents F, Cl, Br, C.sub.1-4 alkyl optionally substituted by halogen, or C.sub.2-4 alkenyl, R.sup.4 represents F, Cl, Br, NO.sub.2, CH.sub.3 or C.sub.2 H.sub.5 and R.sup.5, R.sup.6 and R.sup.7 represent H, F, Cl, Br, NO.sub.2, CH.sub.3 or C.sub.2 H.sub.5, or R.sup.4 and R.sup.5 each represent Cl and R.sup.3, R.sup.6 and R.sup.7 each represent H, R.sup.a and R.sup.b represent H or C.sub.1-4 alkyl, and m is 2 or 3] possess useful herbicidal properties.

  新的酰胺基-N-苯基吡唑衍生物的化学式为：##STR1## [其中 R.sup.1 代表 R.sup.8 C(.dbd.O)--（其中 R.sup.8 代表 H、C.sub.1-7 烷基或C.sub.1-4 烷氧基，可选择地被C.sub.1-4 烷氧基、C.sub.2-5 烷氧羰基或卤素取代，C.sub.3-4 烯氧基，C.sub.3-6 环烷烷基，可选择地被CH.sub.3 或C.sub.2 H.sub.5 取代，或苯氧基，R.sup.2 代表 H 或 R.sup.8 C(.dbd.O)--，或R.sup.1 和R.sup.2 共同代表--CO--(CR.sup.a R.sup.b).sub.m --CO--，R.sup.3 代表 F、Cl、Br、可选择地被卤素取代的C.sub.1-4 烷基，或C.sub.2-4 烯基，R.sup.4 代表 F、Cl、Br、NO.sub.2、CH.sub.3 或C.sub.2 H.sub.5，而 R.sup.5、R.sup.6 和 R.sup.7 代表 H、F、Cl、Br、NO.sub.2、CH.sub.3 或C.sub.2 H.sub.5，或者 R.sup.4 和 R.sup.5 各自代表 Cl，而 R.sup.3、R.sup.6 和 R.sup.7 各自代表 H，R.sup.a 和 R.sup.b 代表 H 或 C.sub.1-4 烷基，m 为 2 或 3] 具有有用的除草特性。
• Herbicidal 5-halo-1-halophenyl-1H-pyrazole-4-carbonitriles
  申请人：Eli Lilly and Company

  公开号：US04563210A1

  公开（公告）日：1986-01-07

  The present invention is directed to herbicidal compounds of the formula ##STR1## wherein each R.sup.1 independently is halogen; R.sub.2 is halo or trifluoromethyl; and n is 1-5; with the provisos that when n is 1, R.sup.1 is other than fluorine, and when n is 2 and each R.sup.1 is chlorine, at least one R.sup.1 is located at a para or ortho position on the phenyl ring.

  本发明涉及式子##STR1##的除草化合物，其中每个R.sup.1独立地是卤素；R.sub.2是卤素或三氟甲基；n为1-5；但有以下限制：当n为1时，R.sup.1不是氟；当n为2且每个R.sup.1是氯时，至少一个R.sup.1位于苯环的对位或邻位。
• Herbicidal 5-amino-4-cyano-1-phenylpyrazoles
  申请人：May & Baker Limited

  公开号：US04629495A1

  公开（公告）日：1986-12-16

  Herbicidal compounds of the formula: ##STR1## wherein A represents R.sup.1 R.sup.2 N-- (wherein R.sup.1 represents C.sub.1-8 alkyl or C.sub.2-8 alkenyl or alkynyl unsubstituted or substituted by CN, OH, C.sub.1-6 alkoxy, carboxy, C.sub.2-9 alkoxycarbonyl, aminocarbonyl optionally substituted by C.sub.1-8 alkyl or C.sub.2-8 alkenyl, C.sub.1-8 alkoxyaminocarbonyl, C.sub.1-8 alkanesulphonamidocarbonyl, --C(.dbd.O)Het, where Het represents a nitrogen-containing heterocyclic group, or one or more halogen atoms or R.sup.1 represents C.sub.3-6 cycloalkyl optionally substituted by C.sub.1-4 alkyl and R.sup.2 represents H or R.sup.1, or R.sup.1 represents C.sub.1-4 alkylthio and R.sup.2 represents H, or A represents R.sup.p (R.sup.q)--C.dbd.N-- (wherein R.sup.p represents C.sub.1-4 alkoxy or amino substituted by one or two C.sub.1-4 alkyl groups and R.sup.q represents H or C.sub.1-4 alkyl) or A represents 2-oxo-azetidin-1-yl, 2-oxo-pyrrolidin-1-yl or 2-oxo-piperidin-1-yl optionally substituted by C.sub.1-6 alkyl or A represents open-chain alkenylcarbonylamino and B represents phenyl substituted in the 2- position by F, Cl, Br, NO.sub.2, Me or Et and in the 4- position by F, Cl, Br, C.sub.1-4 (optionally substituted by halogen) or C.sub.2-4 alkenyl and alkynyl and optionally substituted in the 3-, 5- and 6- positions by F, Cl, Br, NO.sub.2, Me or Et, or B represents 2,3-dichlorophenyl, and salts thereof.

  式子为：##STR1## 其中A代表R.sup.1 R.sup.2 N--（其中R.sup.1代表C.sub.1-8烷基或C.sub.2-8烯基或炔基，未取代或取代CN、OH、C.sub.1-6烷氧基、羧基、C.sub.2-9烷氧基羰基、氨基羰基，可选地取代C.sub.1-8烷基或C.sub.2-8烯基、C.sub.1-8烷氧基氨基羰基、C.sub.1-8烷基磺酰胺基羰基，--C(.dbd.O)Het，其中Het代表含氮杂环基团，或一个或多个卤素原子，或R.sup.1代表可选地取代C.sub.1-4烷基的C.sub.3-6环烷基，R.sup.2代表H或R.sup.1，或R.sup.1代表C.sub.1-4烷基硫基，R.sup.2代表H，或A代表R.sup.p（R.sup.q）--C.dbd.N--（其中R.sup.p代表取代一个或两个C.sub.1-4烷基的C.sub.1-4烷氧基或氨基，R.sup.q代表H或C.sub.1-4烷基），或A代表2-氧代-氮杂环戊酰胺基、2-氧代-吡咯烷酰胺基或2-氧代-哌啶酰胺基，可选地取代C.sub.1-6烷基或A代表开链烯基羰基氨基，B代表在2-位取代F、Cl、Br、NO.sub.2、Me或Et的苯基，且在4-位取代F、Cl、Br、C.sub.1-4（可选地取代卤素）或C.sub.2-4烯基和炔基，可选地在3-、5-和6-位取代F、Cl、Br、NO.sub.2、Me或Et，或B代表2,3-二氯苯基，以及其盐。
• N-phenylpyrazole derivatives
  申请人：MAY & BAKER LIMITED

  公开号：EP0034945A2

  公开（公告）日：1981-09-02

  N-Phenylpyrazole derivatives of the formula:- (wherein each of R5 and R6 represents a C1-C4 alkyl or alkoxy radical, a trifluoromethyl, trifluoromethoxy, nitro, cyano or primary amino radical, or a fluorine, chlorine or bromine atom, each of R', R' and R9 represents a hydrogen atom, a C1-C4 alkyl or alkoxy radical, a trifluoromethyl, trifluoromethoxy, nitro, cyano or primary amino radical or a fluorine, chlorine or bromine atom, or R5, R7, R' and R9 each represents a hydrogen atom and R6 represents a trifluoromethoxy or trifluoromethyl radical, and R10 represents a cyano radical or substituted carbamoyl radical -CONHR", wherein R" represents a methyl or ethyl radical) have been found to possess useful herbicidal properties. All such N-phenylpyrazole derivatives with the exception of 5-amino-4-cyano-1-(2,4-dichlorophenyl)pyrazole and 5-amino-4-cyano-1- (4-chloro-2-methylphenyl)pyrazole are new compounds. Herbicidal compositions containing such N-phenylpyrazole derivatives are described and also processes for the prepararation of the new compounds.

  式中的 N-苯基吡唑衍生物 (其中R5和R6各自代表C1-C4烷基或烷氧基、三氟甲基、三氟甲氧基、硝基、氰基或伯氨基或氟、氯或溴原子，R'、R'和R9各自代表氢原子、C1-C4烷基或烷氧基、三氟甲基、三氟甲氧基、硝基、氰基或伯氨基或氟、R5、R7、R'和 R9 各代表一个氢原子，R6 代表三氟甲氧基或三氟甲基基，R10 代表氰基或取代的氨基甲酰基 -CONHR"，其中 R "代表甲基或乙基）已被发现具有有用的除草特性。除 5-氨基-4-氰基-1-（2,4-二氯苯基）吡唑和 5-氨基-4-氰基-1-（4-氯-2-甲基苯基）吡唑外，所有这些 N-苯基吡唑衍生物都是新化合物。本文介绍了含有此类 N-苯基吡唑衍生物的除草组合物，以及制备这些新化合物的工艺。

表征谱图