5-bromo-2,2-diphenylbenzo[1,3]dioxole | 121171-08-2

• 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: 5-bromo-2,2-diphenylbenzo[1,3]dioxole
• 英文别名: 5-bromo-2,2-diphenyl-1,3-benzodioxole；5-bromo-2,2-diphenyl-1,3-benzodioxol
• CAS: 121171-08-2
• 化学式: C₁₉H₁₃BrO₂
• 分子量: 353.215
• InChiKey: DZPGCBNJLAKMQJ-UHFFFAOYSA-N

物化性质

• 熔点：
  88-89 °C(Solv: ethanol (64-17-5))
• 沸点：
  441.7±45.0 °C(Predicted)
• 密度：
  1.449±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-2,2-diphenylbenzo[1,3]dioxole 在 正丁基锂 、 二氧化硫 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.75h， 以56%的产率得到2,2-diphenylbenzo[1,3]dioxole-5-sulfinic acid
  参考文献：
  名称：

  Benzodioxoles: Novel Cannabinoid-1 Receptor Inverse Agonists for the Treatment of Obesity

  摘要：

  The application of the evolutionary fragment-based de novo design tool TOPology Assigning System (TOPAS), starting from a known CBIR (CB-1 receptor) ligand, followed by further refinement principles, including pharmacophore compliance, chemical tractability, and drug likeness, allowed the identification of benzodioxoles as a novel CB I R inverse agonist series. Extensive multidimensional optimization was rewarded by the identification of promising lead compounds, showing in vivo activity. These compounds reversed the CP-55940-induced hypothermia in Naval Medical Research Institute (NMRI) mice and reduced body-weight gain, as well as fat mass, in diet-induced obese Sprague-Dawley rats. Herein, we disclose the tools and strategies that were employed for rapid hit identification, synthesis and generation of structure-activity relationships, ultimately leading to the identification of (+)-[(R)-2-(2,4-dichloride-phenyl)-6-fluoro-2-(4-fluoro-phenyl)-benzo[1,3]dioxol-5-yl]-morpholin-4-yl-metha- none (R)-14g. Biochemical, pharmacokinetic, and pharmacodynamic characteristics of (R)-14g are discussed.

  DOI：

  10.1021/jm701487t
• 作为产物：
  描述：

  2,2-diphenyl-1,3-benzodioxole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 生成 5-bromo-2,2-diphenylbenzo[1,3]dioxole
  参考文献：
  名称：

  Cephalosporins with sulfur-containing oxyimino side chain

  摘要：

  公式为##STR1##的抗菌化合物，其中R是单核碳环芳基，含有氧或硫原子或亚胺或较低烷基亚胺基作为杂环（非碳）环成员的5-成员芳香杂环基，可选地，一个或两个氮原子，或者含有一个到三个氮原子作为杂环环成员的6-成员芳香杂环基；R.sup.1是氢或在头孢菌素化学中可用的3-取代基；A是较低烷基或可选地取代有羧基、氨基甲酰基、较低烷基氨基甲酰基或二（较低烷基）氨基甲酰基的C.sub.3-7-环烷基；Q是较低烷基或可选地取代有羧基、氨基甲酰基、较低烷基氨基甲酰基或二（较低烷基）氨基甲酰基的C.sub.3-7-环烷基，或者是基团--NR.sup.2--或--NR.sup.2 NR.sup.3--；R.sup.2和R.sup.3独立地是氢或较低烷基；p和m为零或1，n为零、1或2；R.sup.4是氢、较低烷酰基或三（较低烷基）硅基；两个R.sup.4基团一起代表二苯甲亚甲基；R.sup.5是氢、较低烷基、羟基、较低烷氧基、卤素、硝基、--OCOR.sup.7、--OCOOR.sup.71、--N(R.sup.7).sub.2、--NHCOR.sup.7、--NHCOOR.sup.71、--COR.sup.7、--SR.sup.7、--SOR.sup.7、--SO.sub.2 R.sup.7、--SO.sub.3 H、--COOR.sup.7或--CON(R.sup.7).sub.2；R.sup.6是氢、较低烷基或卤素，R.sup.7是氢或较低烷基；R.sup.71是较低烷基，两个--OR.sup.4基团通过相邻碳原子连接到苯环上，以及这些化合物的容易水解的酯和药用可接受盐以及公式I的化合物和其酯和盐的水合物。

  公开号：

  US05036064A1

文献信息

• Aminoindazole derivatives and intermediates, preparation thereof, and pharmaceutical compositions thereof
  申请人：——

  公开号：US20040014802A1

  公开（公告）日：2004-01-22

  The present invention relates to the novel indazole derivatives of general formula (I): 1 in which: R is either O, S or NH; R3 is an alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, aryl, heterocycle, cycloalkyl, alkenyl, etc. radical; these radicals being optionally substituted with one or more substituents; R4, R5, R6 and R7 are chosen, independently of each other, from the following radicals: hydrogen, halogen, CN, NO 2 , NH 2 , OH, COOH, C(O)OR8, —O—C(O)R8, NR8R9, NHC(O)R8, C(O)NR8R9, NHC(S)R8, C(S)NR8R9, SR8, S(O)R8, SO 2 R8, NHSO 2 R8, SO 2 NR8R9, trifluoromethyl, trifluoromethoxy, alkyl, alkoxy, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycle, cycloalkyl, alkenyl, etc.; these radicals being optionally substituted with one or more substituents.

  本发明涉及一般式(I)的新型吲唑衍生物： 1 其中：R为O、S或NH；R3为烷基、芳基、芳基烷基、杂芳基、杂芳基烷基、芳基、杂环、环烷基、烯基等基团；这些基团可以选择性地被一个或多个取代基取代；R4、R5、R6和R7分别选择自以下基团：氢、卤素、CN、NO 2 、NH 2 、OH、COOH、C(O)OR8、—O—C(O)R8、NR8R9、NHC(O)R8、C(O)NR8R9、NHC(S)R8、C(S)NR8R9、SR8、S(O)R8、SO 2 R8、NHSO 2 R8、SO 2 NR8R9、三氟甲基、三氟甲氧基、烷基、烷氧基、芳基、芳基烷基、杂芳基、杂芳基烷基、杂环、环烷基、烯基等；这些基团可以选择性地被一个或多个取代基取代。
• Cephalosporin derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US05438052A1

  公开（公告）日：1995-08-01

  Cephalosporin derivatives have the formula ##STR1## wherein Z.sup.1, Z.sup.2, X, Y, P, Q, m, n and p are as defined in the following text. Also described are the readily hydrolyzable esters and pharmaceutically compatible salts of these compounds, and hydrates of compounds of formula I, their esters and salts. Processes are provided for manufacture and pharmaceutical preparations which contain these compounds. Intermediates from the manufacture of these compounds are described, as is the use of the compounds in the control of illnesses and for the manufacture of the aforementioned preparations.

  头孢菌素衍生物的化学式如下：##STR1## 其中Z.sup.1、Z.sup.2、X、Y、P、Q、m、n和p的定义如下文所述。还描述了这些化合物的易水解酯和药用兼容盐，以及公式I的化合物、它们的酯和盐的水合物。提供了制造和含有这些化合物的制药制剂的过程。描述了制造这些化合物的中间体，以及这些化合物在疾病控制和制备上述制剂中的用途。
• Cephalosphorins with sulfur-containing oxyimino side chain
  申请人：Hoffmann-La Roche Inc.

  公开号：US05073550A1

  公开（公告）日：1991-12-17

  Antibacterial compounds of the formula ##STR1## wherein R is a mononuclear carbocyclic aromatic group, a 5-membered aromatic heterocyclic group which contains as the hetero (non-carbon) ring member(s) an oxygen or sulphur atom or an imino or lower alkylimino group and, optionally, one or two nitrogen atoms, or a 6-membered aromatic heterocyclic group which contains one to three nitrogen atoms as the hetero ring member(s); R.sup.1 is hydrogen or a 3-substituent which is usable in cephalosporin chemistry; A is lower alkylene or C.sub.3-7 cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di-(lower alkyl)carbamoyl; Q is lower alkylene or C.sub.3-7 cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di(lower alkyl)carbamoyl, or the group --NR.sup.2 -- or --NR.sup.2 NR.sup.3 --; R.sup.2 and R.sup.3 are independently hydrogen or lower alkyl; p and m are the zero or 1, n is zero, 1 or 2; R.sup.4 is hydrogen, lower alkanoyl or tri(lower alkyl)silyl; two R.sup.4 groups together represent diphenylmethylene; R.sup.5 is hydrogen, lower alkyl, hydroxy, lower alkoxy, halogen, nitro, --OCOR.sup.7, --OCOOR.sup.71, --N(R.sup.7).sub.2, --NHCOR.sup.7, --NHCOOR.sup.71, --COR.sup.7, --SR.sup.7, --SOR.sup.7, --SO.sub.2 R.sup.7, --SO.sub.3 H, --COOR.sup.7 or --CON(R.sup.7).sub.2 R.sup.6 is hydrogen, lower alkyl or halogen, R.sup.7 is hydrogen or lower alkyl; R.sup.71 is lower alkyl, and the two --OR.sup.4 groups are attached to the phenyl ring via adjacent carbon atoms, as well as readily hydrolyzable esters and pharmaceutically acceptable salts of these compounds and hydrates of compounds of formula I and of their esters and salts.

  化合物的抗菌化合物公式为##STR1##其中R是单核芳香环烃基，5-成员芳香杂环基，其包含氧或硫原子或亚胺或低烷基亚胺基作为杂（非碳）环成员，可选地含有一个或两个氮原子，或者是含有一个到三个氮原子作为杂环成员的6-成员芳香杂环基; R.sup.1是氢或可在头孢菌素化学中使用的3-取代基; A是低烷基或C.sub.3-7环烷基，可选地取代羧基，氨基甲酰基，低烷基氨基甲酰基或二（低烷基）氨基甲酰基; Q是低烷基或C.sub.3-7环烷基，可选地取代羧基，氨基甲酰基，低烷基氨基甲酰基或二（低烷基）氨基甲酰基，或者是--NR.sup.2 --或--NR.sup.2 NR.sup.3 --基团; R.sup.2和R.sup.3独立地是氢或低烷基; p和m为零或1，n为零，1或2; R.sup.4是氢，低烷酰基或三（低烷基）硅基; 两个R.sup.4基团共同代表二苯基甲烯基; R.sup.5是氢，低烷基，羟基，低烷氧基，卤素，硝基，--OCOR.sup.7，--OCOOR.sup.71，--N（R.sup.7）.sub.2，--NHCOR.sup.7，--NHCOOR.sup.71，--COR.sup.7，--SR.sup.7，--SOR.sup.7，--SO.sub.2 R.sup.7，--SO.sub.3 H，--COOR.sup.7或--CON（R.sup.7）.sub.2 R.sup.6是氢，低烷基或卤素，R.sup.7是氢或低烷基; R.sup.71是低烷基，两个--OR.sup.4基团通过相邻的碳原子连接到苯环上，以及这些化合物的易水解酯和药学上可接受的盐以及公式I和其酯和盐的化合物和水合物。
• Intermediates for cephalosporins with sulfur containing oxyimino side
  申请人：Hoffmann-La Roche Inc.

  公开号：US05319140A1

  公开（公告）日：1994-06-07

  Antibacterial compounds of the formula ##STR1## wherein R is a mononuclear carbocyclic aromatic group, a 5-membered aromatic heterocyclic group which contains as the hereto (non-carbon) ring member(s) an oxygen or sulphur atom or an imino or lower alkylimino group and, optionally, one or two nitrogen atoms, or a 6-membered aromatic heterocyclic group which contains one to three nitrogen atoms as the hereto ring member(s); R.sup.1 is hydrogen or a 3-substituent which is usable in cephalosporin chemistry; A is lower alkylene or C.sub.3-7 -cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di(lower alkyl)carbamoyl; Q is lower alkylene or C.sub.3-7 -cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di(lower alkyl)carbamoyl or the group --NR.sup.2 -- or --NR.sup.2 NR.sup.3 --; R.sup.2 and R.sup.3 are independently hydrogen or lower alkyl; p and m are the zero or 1, n is zero, 1 or 2; R.sup.4 is hydrogen, lower alkanoyl or tri(lower alkyl)silyl; two R.sup.4 groups together represent diphenylmethylene; R.sup.5 is hydrogen, lower alkyl, hydroxy, lower alkoxy, halogen, nitro, --OCOR.sup.7, --OCOOR.sup.71, --N(R.sup.7).sub.2, --NHCOR.sup.7, --NHCOOR.sup.71, --COR.sup.7, --SR.sup.7, --SOR.sup.7, --SO.sub.2 R.sup.7, --SO.sub.3 H, --COOR.sup.7 or --CON(R.sup.7).sub.2 ; R.sup.6 is hydrogen, lower alkyl or halogen, R.sup.7 is hydrogen or lower alkyl; R.sup.71 is lower alkyl, and the two --OR.sup.4 groups are attached to the phenyl ring via adjacent carbon atoms, as well as readily hydrolyzable esters and pharmaceutically acceptable salts of these compounds and hydrates of compounds of formula I and of their esters and salts.

  公式为 ##STR1## 的抗菌化合物，其中 R 是单核芳香烃基，5-成员芳香杂环基，其中含有氧或硫原子或亚胺或低烷基亚胺基作为其（非碳）环成员，可选地含有一或两个氮原子，或6-成员芳香杂环基，其中含有一到三个氮原子作为其环成员; R.sup.1 是氢或可用于头孢菌素化学中的3-取代基; A 是低烷基或C.sub.3-7-环戊烷基，可选地取代为羧基，氨基甲酰基，低烷基氨基甲酰基或二（低烷基）氨基甲酰基; Q 是低烷基或C.sub.3-7-环戊烷基，可选地取代为羧基，氨基甲酰基，低烷基氨基甲酰基或二（低烷基）氨基甲酰基或基团--NR.sup.2--或--NR.sup.2NR.sup.3--; R.sup.2 和 R.sup.3 分别是氢或低烷基; p 和 m 为零或1，n 为零、1或2; R.sup.4 是氢、低烷酰基或三（低烷基）硅基; 两个 R.sup.4 组成二苯甲基; R.sup.5 是氢、低烷基、羟基、低烷氧基、卤素、硝基、--OCOR.sup.7、--OCOOR.sup.71、--N(R.sup.7).sub.2、--NHCOR.sup.7、--NHCOOR.sup.71、--COR.sup.7、--SR.sup.7、--SOR.sup.7、--SO.sub.2R.sup.7、--SO.sub.3H、--COOR.sup.7或--CON(R.sup.7).sub.2; R.sup.6 是氢、低烷基或卤素，R.sup.7 是氢或低烷基; R.sup.71 是低烷基，两个--OR.sup.4基通过相邻碳原子连接到苯环上，以及这些化合物的容易水解的酯和药学上可接受的盐以及公式I和其酯和盐的化合物和水合物。
• Intermediates for cephalosporins with sulfur-containing oxyimino side
  申请人：Hoffmann-La Roche, Inc.

  公开号：US05138066A1

  公开（公告）日：1992-08-11

  Antibacterial compounds of the formula ##STR1## wherein R is a mononuclear carbocyclic aromatic group, a 5-membered aromatic heterocyclic group which contains as the hetero (non-carbon) ring member(s) an oxygen or sulphur atom or an imino or lower alkylimino group and, optionally, one or two nitrogen atoms, or a 6-membered aromatic heterocyclic group which contains one to three nitrogen atoms as the hetero ring member(s); R.sup.1 is hydrogen or a 3-substituent which is usable in cephalosporin chemistry; A is lower alkylene or C.sub.3-7 -cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di(lower alkyl)carbamoyl; Q is lower alkylene or C.sub.3-7 -cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di(lower alkyl)carbamoyl, or the group --NR.sup.2 -- or --NR.sup.2 NR.sup.3 --; R.sup.2 and R.sup.3 are independently hydrogen or lower alkyl; p and m are the zero or 1, n is zero, 1 or 2; R.sup.4 is hydrogen, lower alkanoyl or tri(lower alkyl)silyl; two R.sup.4 groups together represent diphenylmethylene; R.sup.5 is hydrogen, lower alkyl, hydroxy, lower alkoxy, halogen, nitro, --OCOR.sup.7, --OCOOR.sup.71, --N(R.sup.7).sub.2, --NHCOR.sup.7, --NHCOOR.sup.71, --COR.sup.7, --SR.sup.7, --SOR.sup.7, --SO.sub.2 R.sup.7, --SO.sub.3 H, --COOR.sup.7 or --CON(R.sup.7).sub.2 ; R.sup.6 is hydrogen, lower alkyl or halogen, R.sup.7 is hydrogen or lower alkyl; R.sup.71 is lower alkyl, and the two --OR.sup.4 groups are attached to the phenyl ring via adjacent carbon atoms, as well as readily hydrolyzable esters and pharmaceutically acceptable salts of these compounds and hydrates of compounds of formula I and of their esters and salts.

  化合物的抗菌成分的公式为##STR1##其中R是单核芳香碳环基团，5-成员芳香杂环基团，其中包含杂（非碳）环成员的氧或硫原子或亚胺或低烷基亚胺基团，并且可选地包含一个或两个氮原子，或者是包含1至3个氮原子的6-成员芳香杂环基团；R.sup.1是氢或可用于头孢菌素化学的3-取代基；A是低烷基或C.sub.3-7-环烷基，可选地取代羧基，氨基甲酰基，低烷基氨基甲酰基或二（低烷基）氨基甲酰基；Q是低烷基或C.sub.3-7-环烷基，可选地取代羧基，氨基甲酰基，低烷基氨基甲酰基或二（低烷基）氨基甲酰基，或者是--NR.sup.2--或--NR.sup.2NR.sup.3--基团；R.sup.2和R.sup.3独立地是氢或低烷基；p和m为0或1，n为0、1或2；R.sup.4是氢，低烷酰基或三（低烷基）硅基；两个R.sup.4基团一起代表二苯甲基；R.sup.5是氢，低烷基，羟基，低烷氧基，卤素，硝基，--OCOR.sup.7，--OCOOR.sup.71，--N（R.sup.7）.sub.2，--NHCOR.sup.7，--NHCOOR.sup.71，--COR.sup.7，--SR.sup.7，--SOR.sup.7，--SO.sub.2R.sup.7，--SO.sub.3H，--COOR.sup.7或--CON（R.sup.7）.sub.2；R.sup.6是氢，低烷基或卤素，R.sup.7是氢或低烷基；R.sup.71是低烷基，两个--OR.sup.4基团通过相邻碳原子连接到苯环上，以及这些化合物的容易水解的酯和药学上可接受的盐以及公式I和它们的酯和盐的化合物和水合物。