5-(bromomethyl)-4,5-dihydro-3,3-diphenyl-2(3H)-furanone | 83160-36-5

• 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-(bromomethyl)-4,5-dihydro-3,3-diphenyl-2(3H)-furanone
• 英文别名: 5-(bromomethyl)-3,3-diphenyldihydrofuran-2(3H)-one；2,2-diphenyl-5-bromo-4-pentanolide；5-bromomethyl-3,3-diphenyl-dihydro-furan-2-one；5-Brommethyl-3,3-diphenyl-dihydro-furan-2-on；5-(bromomethyl)-4,5-dihydro-3,3-diphenyl-2(3H)furanone；5-Brom-4-hydroxy-2,2-diphenyl-pentansaeure-lacton；5-(bromomethyl)-3,3-diphenyloxolan-2-one
• CAS: 83160-36-5
• 化学式: C₁₇H₁₅BrO₂
• 分子量: 331.209
• InChiKey: LFNWFGDMNXCZMD-UHFFFAOYSA-N

物化性质

• 熔点：
  87-88 °C
• 沸点：
  475.1±45.0 °C(Predicted)
• 密度：
  1.395±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(bromomethyl)-4,5-dihydro-3,3-diphenyl-2(3H)-furanone 在 二叔丁基过氧化物 、 tri-n-butylcrotyltin 作用下， 以 xylene 为溶剂， 反应 8.0h， 以78%的产率得到5-methyl-3,3-diphenyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Hydrogen transfer from crotyltri-n-butylstannane to carbon radicals

  摘要：

  DOI：

  10.1016/s0022-328x(00)98720-5
• 作为产物：
  描述：

  methyl 2,2-diphenylpent-4-enoate 在 四氯化碳 、 溴 作用下， 生成 5-(bromomethyl)-4,5-dihydro-3,3-diphenyl-2(3H)-furanone
  参考文献：
  名称：

  The Chemistry of 2,2-Diphenyl-4-pentenoic and 2,2-Diphenyl-4-methyl-4-pentenoic Acids¹

  摘要：

  DOI：

  10.1021/ja01167a022

文献信息

• Synthesis and antimuscarinic properties of some N-substituted 5-(aminomethyl)-3,3-diphenyl-2(3H)-furanones
  作者：Carl Kaiser、Ciro J. Spagnuolo、Theodore C. Adams、Vicki H. Audia、Andrea C. Dupont、Holia Hatoum、Valerie C. Lowe、Judith C. Prosser、Bonnie L. Sturm、Lalita Noronha-Blob

  DOI：10.1021/jm00101a019

  日期：1992.11

  selective antimuscarinic drugs with potential utility in the treatment of urinary incontinence associated with bladder muscle instability, a series of N-substituted 5-(aminomethyl)-3,3-diphenyl-2(3H)-furanones, conformationally-constrained lactone relatives of benactyzine, was prepared. The compounds were examined in several paradigms that measure muscarinic (M1, M2, and M3) receptor antagonist activity

  在一项旨在开发新的选择性抗毒蕈碱药物的研究中，该药物在治疗与膀胱肌不稳相关的尿失禁中具有潜在的实用性，一系列N-取代的5-（氨基甲基）-3,3-二苯基-2（3H）-呋喃酮，制备了受构造约束的贝内替嗪的内酯亲戚。在衡量毒蕈碱（M1，M2和M3）受体拮抗剂活性的几种范例中检查了这些化合物。研究了在这些测试中显示出效力和/或选择性的系列成员中的一些成员对豚鼠膀胱收缩，瞳孔散大和唾液分泌的影响。这些研究表明，将氨基官能团并入咪唑或吡唑环中会产生一些新颖，有效和选择性的抗毒蕈碱剂。咪唑位置2的适当烷基取代显着影响毒蕈碱，特别是M3受体活性，并可能反映相互作用的互补位点。一些化合物在膀胱造影（CMG）模型中选择性降低了膀胱压力，而没有产生散瞳和唾液效应。在这些体内方案中，该系列几种化合物的单独作用和不同作用表明，毒蕈碱受体亚型可能与先前表征的分子克隆亚群相对应。在本文中，讨论了一系列取代内酯的构效关系
• 5-(1-(imidazol)methyl)-3,3-disubstituted-2(3H)furanone derivatives
  申请人：Marion Merrell Dow Inc.

  公开号：US05039691A1

  公开（公告）日：1991-08-13

  Furanone compounds and compositions having anticholinergic activity are described. The compounds have the formula: ##STR1## wherein: the dashed line indicates either the 4,5-unsaturated or the 4,5-dihydrofuranone ring; R.sub.1 and R.sub.2 may be the same or different and are hydrogen, thienyl, furanyl, or cycloalkyl (C.sub.3 -C.sub.6), benzyl, phenyl, substituted phenyl or substituted benzyl wherein the phenyl or benzyl group may be substituted with halogen, trifluoromethyl, lower alkyl, lower alkoxy or hydroxy; R.sub.3, R.sub.4 and R.sub.5 may be the same or different and are hydrogen, lower alkyl, lower alkyl substituted with a halogen, alkoxy, amino or carboxylic acid group, an alkyl or alkylene bridge between R.sub.4 and R.sub.5 or R.sub.3 and the ring N, trifluoromethyl, nitro, a cycloalkyl group containing 3 to 6 carbons, halogen, benzyl, phenyl, substituted phenyl or substituted benzyl, for which the substituents are the same as those set forth for R.sub.1 and R.sub.2 substituted benzyl or phenyl. R.sub.6 in the dihydrofuranone series is hydrogen or lower alkyl. Also described are the pharmaceutically acceptable quaternary alkyl and acid addition salts of such compounds. The compounds are particularly useful in the treatment of neurogenic bladder disorder and chronic obstructive pulmonary diseases.

  描述了具有抗胆碱作用的呋喃酮化合物和组合物。这些化合物的化学式为：##STR1##其中：虚线表示4,5-不饱和或4,5-二氢呋喃酮环；R.sub.1和R.sub.2可以相同也可以不同，可以是氢、噻吩基、呋喃基、环丙烷基（C.sub.3 -C.sub.6）、苄基、苯基、取代苯基或取代苄基，其中苯基或苄基可能被卤素、三氟甲基、低烷基、低烷氧基或羟基取代；R.sub.3、R.sub.4和R.sub.5可以相同也可以不同，可以是氢、低烷基、带有卤素、烷氧基、氨基或羧酸基的取代低烷基，R.sub.4和R.sub.5之间或R.sub.3和环N之间的烷基或烷基烯桥，三氟甲基、硝基、含有3至6个碳原子的环丙烷基、卤素、苄基、苯基、取代苯基或取代苄基，其取代基与R.sub.1和R.sub.2中所述的相同，取代苄基或苯基。二氢呋喃酮系列中的R.sub.6是氢或低烷基。还描述了这些化合物的药用可接受的季铵烷基和酸盐。这些化合物在治疗神经源性膀胱障碍和慢性阻塞性肺疾病方面特别有用。
• Regioselective (Diacetoxyiodo)benzene-Promoted Halocyclization of Unfunctionalized Olefins
  作者：Gong-Qing Liu、Yue-Ming Li

  DOI：10.1021/jo501739j

  日期：2014.11.7

  A metal-free method for intramolecular halocyclization of unfunctionalized olefins was detailed. (Diacetoxyiodo)benzene (PIDA) was very effective for haloamidation, haloetherification, and halolactonization of unfunctionalized olefins. In the presence of 1.1 equiv of PIDA and suitable halogen sources, a variety of unfunctionalized olefins could be converted to the corresponding 1,2-bifunctional cyclic

  详细介绍了一种用于非官能化烯烃分子内卤代化的无金属方法。（二乙酰氧基碘）苯（PIDA）对于未官能化烯烃的卤代酰胺化，卤代醚化和卤代内酯化非常有效。在存在1.1当量的PIDA和合适的卤素源的情况下，可以将各种未官能化的烯烃以良好或优异的分离产率转化为相应的1,2-双官能环状骨架，并且可以高收率获得生物学上有意义的化合物的关键中间体通过亲核取代由此获得的卤代环化产物在温和条件下获得收率。
• 5-[1-(Imidazol)methyl]-3,3-disubstituted-2(3H) furanone derivatives
  申请人：MARION MERRELL DOW INC.

  公开号：EP0455909A2

  公开（公告）日：1991-11-13

  Furanone compounds and compositions having anticholinergic activity are described. The compounds have the formula: wherein: the dashed line indicates either the 4,5-unsaturated or the 4,5-dihydrofuranone ring; R and R2 may be the same or different and are hydrogen, thienyl, furanyl, or cycloalkyl (C3-C6), benzyl, phenyl, substituted phenyl or substituted benzyl wherein the phenyl or benzyl group may be substituted with halogen, trifluoromethyl, lower alkyl, lower alkoxy or hydroxy; Ra, R4 and R5 may be the same or different and are hydrogen, lower alkyl, lower alkyl substituted with a halogen, alkoxy, amino or carboxylic acid group, an alkyl or alkylene bridge between R4 and R5 or R3 and the ring N, trifluoromethyl, nitro, a cycloalkyl group containing 3 to 6 carbons, halogen, benzyl, phenyl, substituted phenyl or substituted benzyl, for which the substituents are the same as those set forth for R1 and R2 substituted benzyl or phenyl. R6 in the dihydrofuranone series is hydrogen or lower alkyl. Also described are the pharmaceutically acceptable quaternary alkyl and acid addition salts of such compounds The compounds are cholinergic receptor antagonists, and are particulary useful in the treatment of neurogenic bladder disorder and chronic obstructive pulmonary diseases.

  描述了具有抗胆碱能活性的呋喃酮化合物和组合物。这些化合物具有如下式子 其中 虚线表示 4，5-不饱和环或 4，5-二氢呋喃酮环； R 和 R2 可以相同或不同，并且是氢、噻吩基、呋喃基或环烷基（C3-C6）、苄基、苯基、取代苯基或取代苄基，其中苯基或苄基可被卤素、三氟甲基、低级烷基、低级烷氧基或羟基取代； Ra、R4 和 R5 可以相同或不同，并且是氢、低级烷基、被卤素、烷氧基、氨基或羧酸基取代的低级烷基、R4 和 R5 之间的烷基或亚烷基桥或 R3 和环 N、三氟甲基、硝基、含 3 至 6 个碳的环烷基、卤素、苄基、苯基、取代的苯基或取代的苄基，其取代基与 R1 和 R2 取代的苄基或苯基的取代基相同。 二氢呋喃酮系列中的 R6 是氢或低级烷基。 这些化合物是胆碱能受体拮抗剂，特别适用于治疗神经源性膀胱失调和慢性阻塞性肺病。
• Mercurial Diuretics. III. Mercuration of Allylacetic Acid and Related Compounds
  作者：R. L. Rowland、Wendell L. Perry、Harris L. Friedman

  DOI：10.1021/ja01147a046

  日期：1951.3