3,4-dimethoxy-3'-nitro-benzophenone | 108620-68-4

• 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: 3,4-dimethoxy-3'-nitro-benzophenone
• 英文别名: 3,4-Dimethoxy-3'-nitro-benzophenon；(3,4-Dimethoxyphenyl)(3-nitrophenyl)methanone；(3,4-dimethoxyphenyl)-(3-nitrophenyl)methanone
• CAS: 108620-68-4
• 化学式: C₁₅H₁₃NO₅
• mdl: MFCD11983361
• 分子量: 287.272
• InChiKey: ORVKKDSFBZEODB-UHFFFAOYSA-N

物化性质

• 熔点：
  135 °C
• 沸点：
  454.9±45.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-dimethoxy-3'-nitro-benzophenone 在 吡啶 、 铁粉 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 5-tert-butyl-N-[3-(3,4-dimethoxybenzoyl)phenyl]-2-methylpyrazole-3-carboxamide
  参考文献：
  名称：

  Utility of Complementary Molecular Reactivity and Molecular Recognition (CMR/R) Technology and Polymer-Supported Reagents in the Solution-Phase Synthesis of Heterocyclic Carboxamides

  摘要：

  The use of our recently reported chemical library purification strategy in the development of a herbicidal lead, N-(3-benzoylphenyl)-3-(1,1-dimethylethyl)-1-methyl-1H-pyrazole-5-carboxamide (3), is described. The approach applying fundamental properties of complementary molecular reactivity and molecular recognition (CMR/R) as the basis for a general purification strategy was utilized. Polymeric reagents were used in the synthesis to generate reactive species involved in product formation, and complementary molecular reactivity/molecular recognition polymer 8 (CMR/R polymer 8) was used in the solution-phase syntheses of building blocks, primary libraries, and lead refinement libraries. An extension of the CMR/R methodology was applied, utilizing a sequestration enabling reagent (SER), transforming a reactant into an electrophilic species sequestrable by CMR/R polymer 8. This library purification strategy enabled rapid lead generation and lead refinement to afford herbicide 27o. The CMR/R solid-phase purification technique enabled a simple, general, and powerful protocol, eliminating the usual tedious and time-consuming methods required for solution-phase product purification. The result was the synthesis of hundreds of compounds, prepared in a relatively short time, leading to a compound with a 4-fold improvement in herbicidal activity over the initial lead.

  DOI：

  10.1021/jo970571i
• 作为产物：
  描述：

  邻苯二甲醚 、 间硝基苯甲酰氯 在 三氯化铝 作用下， 以 二氯甲烷 、 水 为溶剂， 以2.21 g (39%)的产率得到3,4-dimethoxy-3'-nitro-benzophenone
  参考文献：
  名称：

  Immunotherapeutic agents

  摘要：

  取代苯乙烯的氰基和羧基衍生物是肿瘤坏死因子 .alpha.、核因子 .kappa.B 和磷酸二酯酶的抑制剂，可用于对抗消瘦症、内毒素休克、逆转录病毒复制、哮喘和炎症性疾病。一个典型的实施例是3,3-双-(3,4-二甲氧基苯基)丙烯腈。

  公开号：

  US05929117A1

文献信息

• Cyclobutene derivatives, their preparation and their therapeutic uses
  申请人：Sankyo Company, Limited

  公开号：US06329405B1

  公开（公告）日：2001-12-11

  Compounds of formula (I): {wherein: R1 and R2 each represents a variety of organic groups; R3 and R4 each represents hydrogen or a variety of organic groups; A represents a group of formula (A-1): [wherein: R5 represents hydrogen, hydroxy or alkyl, R6 represents hydroxy, alkoxy, alkylthio or an amine residue, X and Y each represents oxygen or sulfur, and Z represents a direct single bond between the nitrogen atom shown and the benzene ring shown in formula (I), or an alkylene group], G represents a single bond, alkylene or substituted alkylene; the broken line represents a single or double bond; when the broken line represents a double bond, D represents a carbon atom; and E represents an ═N—O— group; when the broken line represents a single bond, D represents a CH group or a nitrogen atom, and E represents an oxygen atom, a sulfur atom, an —NH— group or a —CO— group}; and pharmaceutically acceptable salts, esters or other derivatives thereof have the ability to inhibit an ileal bile transporter and so may be used to treat or prevent hypercholesterolemia.

  式(I)的化合物： 其中：R1和R2分别代表各种有机基团；R3和R4分别代表氢或各种有机基团；A代表式(A-1)的基团： [其中：R5代表氢、羟基或烷基，R6代表羟基、烷氧基、烷基硫氧基或胺基残基，X和Y分别代表氧或硫，Z代表氮原子与式(I)中所示苯环之间的直接单键，或者是一个烷基链]， G代表单键、烷基或取代烷基；虚线代表单键或双键；当虚线代表双键时，D代表碳原子；E代表一个-N—O—基团；当虚线代表单键时，D代表一个CH基团或一个氮原子，E代表一个氧原子、硫原子、一个—NH—基团或一个—CO—基团；以及药学上可接受的盐、酯或其他衍生物具有抑制回肠胆汁转运蛋白的能力，因此可用于治疗或预防高胆固醇血症。
• [EN] NOVEL IMMUNOTHERAPEUTIC AGENTS AND THEIR USE IN THE REDUCTION OF CYTOKINE LEVELS<br/>[FR] AGENTS IMMUNOTHERAPIQUES ET LEUR UTILISATION POUR FAIRE BAISSER LES TENEURS EN CYTOKINES
  申请人：CELGENE CORPORATION

  公开号：WO1998006692A1

  公开（公告）日：1998-02-19

  (EN) Cyano and carboxy derivatives of substituted styrenes of formula (I), in which Y is -COZ, -C$m(Z)N, or lower alkyl of 1 to 5 carbon atoms; Z is -OH, -NR6R6, -R7, or -OR7; X, R1, R2, R3, R4, R5, R6, and R7 have the values given in the description are inhibitors of tumor necrosis factor $g(a), nuclear factor $g(k)B, and phosphodiesterase and can be used to combat cachexia, endotoxic shock, retrovirus replication, asthma, and inflammatory conditions. A typical embodiment is 3,3-bis-(3,4-dimethoxyphenyl)acrylonitrile.(FR) La présente invention concerne des dérivés cyano et carboxy de styrènes substitués représentés par la formule générale (I). Dans cette formule, Y est -COZ, -C$m(Z)N ou alkyle inférieur en C1-C5; Z est -OH, -NR6R6, -R7 ou -OR7; X, R1, R2, R3, R4, R5, R6 et R7 ont les valeurs données dans la description. Ces dérivés, qui sont des inhibiteurs du facteur de nécrose tumorale $g(a), du facteur nucléaire $g(k)B et de la phosphodiestérase, conviennent au traitement de la cachexie, du choc endotoxique, de la réplication rétrovirale, de l'asthme, et des affections inflammatoires. Le 3,3-bis-(3,4-diméthoxyphényl)acrylonitrile est un exemple type de tels dérivés.

  该文献描述了一类化合物，其化学式为(I)，其中Y为-COZ，-C$m(Z)N或1至5个碳原子的低级烷基；Z为-OH，-NR6R6，-R7或-OR7；X，R1，R2，R3，R4，R5，R6和R7的值在描述中给出。这些化合物是肿瘤坏死因子$g(a)，核因子$g(k)B和磷酸二酯酶的抑制剂，可用于对抗消瘦症，内毒素休克，逆转录病毒复制，哮喘和炎症等疾病。其中3,3-双-(3,4-二甲氧基苯基)丙烯腈是一个典型的实施例。
• Novel immunotherapeutic agents
  申请人：——

  公开号：US20010056107A1

  公开（公告）日：2001-12-27

  Cyano and carboxy derivatives of substituted styrenes are inhibitors of tumor necrosis factor &agr;, nuclear factor &kgr;B, and phosphodiesterase and can be used to combat cachexia, endotoxic shock, retrovirus replication, asthma, and inflammatory conditions. A typical embodiment is 3,3-bis-(3,4-dimethoxyphenyl)acrylonitrile.

  取代苯乙烯的氰基和羧基衍生物是肿瘤坏死因子α、核因子κB和磷酸二酯酶的抑制剂，可用于对抗消瘦症、内毒素休克、逆转录病毒复制、哮喘和炎症状况。一个典型的实施例是3,3-双-(3,4-二甲氧基苯基)丙烯腈。
• Cyclobutene derivatives
  申请人：Sankyo Company Limited

  公开号：EP1070703A1

  公开（公告）日：2001-01-24

  Compounds of formula (I): in which: R1 and R2 each represents a variety of organic groups; R3 and R4 each represents hydrogen or a variety of organic groups; A represents a group of formula (A-1):    [in which: R5 represents hydrogen, hydroxy or alkyl, R6 represents hydroxy, alkoxy, alkylthio or an amine residue, X and Y each represents oxygen or sulphur, and Z represents a direct single bond between the nitrogen atom shown and the benzene ring shown in formula (I), or an alkylene group], G represents a single bond, alkylene or substituted alkylene; the broken line represents a single or double bond; when the broken line represents a double bond, D represents a carbon atom; and E represents an =N-O- group; when the broken line represents a single bond, D represents a CH group or a nitrogen atom, and E represents an oxygen atom, a sulphur atom, an -NH- group or a -CO- group}; and pharmaceutically acceptable salts, esters or other derivatives thereof have the ability to inhibit an ileal bile transporter and so may be used to treat or prevent hypercholesterolaemia.

  式(I)化合物： 其中R1 和 R2 各自代表各种有机基团；R3 和 R4 各自代表氢或各种有机基团；A 代表式（A-1）的基团： 其中R5代表氢、羟基或烷基，R6代表羟基、烷氧基、烷硫基或胺残基，X和Y各自代表氧或硫，Z代表式（I）所示的氮原子和苯环之间的直接单键或亚烷基]、 G 代表单键、亚烷基或取代亚烷基；断线代表单键或双键；当断线代表双键时，D 代表碳原子；E 代表 =N-O- 基团；当断线代表单键时，D代表CH基团或氮原子，E代表氧原子、硫原子、-NH-基团或-CO-基团}；其药学上可接受的盐、酯或其他衍生物具有抑制回肠胆汁转运体的能力，因此可用于治疗或预防高胆固醇血症。
• Novel immunotherapeutic agents and their use in the reduction of cytokine levels
  申请人：CELGENE CORPORATION

  公开号：EP1361210A2

  公开（公告）日：2003-11-12

  Cyano and carboxy derivatives of substituted styrenes of formula I (a) X is -(CnH2n)- in which n has a value of 1, 2 or 3, and R1 is alkyl of 1 to 10 carbon atoms, monocycloaIkyl of up to 10 carbon atoms, polycycloalkyl of up to 10 carbon atoms, or benzocyclic alkyl of up to 10 carbon atoms, or (b) X is -CH= and R1 is alkylidene of up to 10 carbon atoms, monocycloalkylidene of up to 10 carbon atoms, or bicycloalkylidene of up to 10 carbon atoms; R2is hydrogen, nitro, cyano, trifluoromethyl, carbethoxy, carbomethoxy, carbopropoxy, acetyl, carbamoyl, acetoxy, carboxy, hydroxy, amino, alkyl of 1 to 6 carbon atoms, alkylidenemethyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, or halo; and R3is (i) phenyl, unsubstituted or substituted with I or more substituents each selected independently from nitro, cyano, halo, trifluoromethyl, carbethoxy, carbomethoxy, carbopropoxy, acetyl, carbamoyl, or carbamoyl substituted with alkyl of 1 to 3 carbon atoms, acetoxy, carboxy, hydroxy, amino, amino substituted with an alkyl of 1 to 5 carbon atoms, alkyl of up to 10 carbon atoms, cycloalkyl of up to 10 carbon atoms, alkoxy of up to 10 carbon atoms, cycloalkoxy of up to 10 carbon atoms, alkylidenemethyl of up to 10 carbon atoms, cycloalkylidenemethyl of up to 10 carbon atoms, phenyl, or methylenedioxy; (ii) pyridine, substituted pyridine, pyrrolidine, imidizole, naphthalene, or thiophene; (iii) cycloalkyl of 4 -10 carbon atoms, unsubstituted or substituted with 1 or more substituents each selected independently from the group consisting of nitro, cyano, halo, trifluoromethyl, carbethoxy, carbomethoxy, carbopropoxy, acetyl, carbamoyl, acetoxy, carboxy, hydroxy, amino, substituted amino, alkyl of 1 to 10 carbon atoms, alkoxy of 1 to 10 carbon atoms, phenyl; each of R4 and R5 taken individually is hydrogen or R4 and R5 taken together are a carbon-carbon bond; Yis -C≡ N, or when R4 and R5 are hydrogen, Y is alternatively -COZ with the provisos that; (iv) when Y is -COZ, Z is -NHR6R6 and R6 is hydrogen, then R1 is not methyl; (v) when Y is -COZ, Z is -OH or -OR7 and R7 is benzyl, then R1 is not methyl; and (vi) when Y is -COZ and Z is R7 benzyl, then R1 is not methyl and R3 is hydroxy substituted phenyl. Z is -OH, -NR6R6, R7 or OR7; R6is hydrogen or alkyl of 1 to 6 carbon atoms; and R7is alkyl or benzyl; are inhibitors of tumor necrosis factor α, and nuclear factor kB and phosphodiesterase and can be used to combat cachexia, endotoxic shock, retrovirus replication, asthma, and inflammatory conditions.

  式 I 的取代苯乙烯的氰基和羧基衍生物 (a) X 是-(CnH2n)-，其中 n 的值为 1、2 或 3，且 R1 是 1 至 10 个碳原子的烷基、最多 10 个碳原子的单环烷基、最多 10 个碳原子的多环烷基或最多 10 个碳原子的苯环烷基，或 (b) X 为-CH=，R1 为碳原子数不超过 10 的亚烷基、碳原子数不超过 10 的单环亚烷基或碳原子数不超过 10 的双环亚烷基； R2 是氢、硝基、氰基、三氟甲基、甲氧基、碳甲氧基、碳丙氧基、乙酰基、氨基甲酰基、乙酰氧基、羧基、羟基、氨基、1 至 6 个碳原子的烷基、1 至 6 个碳原子的亚烷基甲基、1 至 6 个碳原子的烷氧基或卤素；和 R3 是 (i) 苯基，未取代或被 I 个或多个取代基取代，每个取代基独立选自硝基、氰基、卤代、三氟甲基、甲氧羰基、甲氧羰基、甲丙氧基、乙酰基、氨基甲酰基或被 1 至 3 个碳原子的烷基取代的氨基甲酰基、乙酰氧基、羧基、羟基、氨基、被 1 至 6 个碳原子的烷基取代的亚烷基甲基、被 1 至 6 个碳原子的烷氧基取代的亚烷基甲基、被 1 至 6 个碳原子的烷氧基取代的烷基或卤代、被 1 至 5 个碳原子的烷基、最多 10 个碳原子的烷基、最多 10 个碳原子的环烷基、最多 10 个碳原子的烷氧基、最多 10 个碳原子的环烷氧基、最多 10 个碳原子的亚烷基甲基、最多 10 个碳原子的亚环烷基甲基、苯基或亚甲基二氧基取代的氨基；(ii) 吡啶、取代吡啶、吡咯烷、咪唑、萘或噻吩；(iii) 4-10 个碳原子的环烷基，未被取代或被 1 个或 1 个以上各自独立选自以下组别的取代基取代：硝基、氰基、卤代、三氟甲基、碳乙氧基、碳甲氧基、碳丙氧基、乙酰基、氨基甲酰基、乙酰氧基、羧基、羟基、氨基、取代氨基、1-10 个碳原子的烷基、1-10 个碳原子的烷氧基、苯基； R4 和 R5 中的每一个单独来看都是氢，或者 R4 和 R5 合在一起是碳-碳键； Y是-C≡N，或者当R4和R5是氢时，Y是-COZ，但条件是： (iv) 当 Y 为-COZ，Z 为-NHR6R6，R6 为氢时，R1 不是甲基； (v) 当 Y 为-COZ、Z 为-OH 或-OR7 且 R7 为苄基时，R1 不是甲基；以及 (vi) 当 Y 为-COZ，Z 为-OH 或-OR7，R7 为苄基时，R1 不是甲基，R3 为羟基取代的苯基。 Z 是-OH、-NR6R6、R7 或 OR7； R6 是氢或 1 至 6 个碳原子的烷基；以及 R7 是烷基或苄基；是肿瘤坏死因子 α、核因子 kB 和磷酸二酯酶的抑制剂，可用于防治恶病质、内毒素休克、逆转录病毒复制、哮喘和炎症。