FLA 873 | 101460-36-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: FLA 873
• 英文别名: (S)-5-Bromo-2,6-dimethoxy-N-<(1-ethyl-2-pyrrolidinyl)methyl>-3-hydroxybenzamide；(S)-5-Bromo-2,6-dimethoxy-N-[(1-ethyl-2-pyrrolidinyl)methyl]-3-hydroxybenzamide；(S)-3-Bromo-N-((1-ethylpyrrolidin-2-yl)methyl)-5-hydroxy-2,6-dimethoxybenzamide；3-bromo-N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-5-hydroxy-2,6-dimethoxybenzamide
• CAS: 101460-36-0
• 化学式: C₁₆H₂₃BrN₂O₄
• 分子量: 387.274
• InChiKey: NLIPZVMIMUCCIK-JTQLQIEISA-N

物化性质

• 沸点：
  452.8±45.0 °C(Predicted)
• 密度：
  1.355±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  71
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,6-二甲氧基苯甲酸 在 盐酸 、 氯化亚砜 、 溴 、 对甲苯磺酸 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 间氯过氧苯甲酸 、 三氟乙酸酐 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 丙酮 、 甲苯 、 三氟乙酸 为溶剂， 反应 83.5h， 生成 FLA 873
  参考文献：
  名称：

  Pivaloyl-directed regioselective syntheses of 2,3,6-trioxygenated benzamides: phenolic metabolites of remoxipride

  摘要：

  The regioselective syntheses of (S)-5-bromo-2,6-dimethoxy-N-[(1-ethyl-2-pyrrolidinyl)methyl]-3-hydroxybenzamide (2) and (S)-5-bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-3-hydroxy-6-methoxy-salicylamide (3) from 2,6-dimethoxybenzoic acid and 4-methoxycatechol are described. The latter compound was protected and ortho-lithiated to introduce the carboxyl function in a regioselective manner. Regiocontrol in bromination and demethylation was achieved by introduction of a bulky pivaloyl group. This strategy also enabled the use of a common intermediate as an alternative synthesis of the catechol 3.

  DOI：

  10.1021/jo00065a015

文献信息

• Derivatives of N-(2-pyrrolidinylmethyl)-benzamide, process for their preparation, intermediates and a pharmaceutical preparation
  申请人：Astra Läkemedel Aktiebolag

  公开号：EP0156776A1

  公开（公告）日：1985-10-02

  Novel therapeutically active compounds of the formula wherein Z , being Z1, Z2 or Z3, is the same or different and selected among OH, OR', NH2, NR24, NHR', SH, SR4 and OR4 wherein R' is a formyl group, an acyl group, an alkoxycarbonyl group or a mono- or dialkylcarbamoyl group and R4 is a lower alkyl group, R2 is a hydrogen, a halogen, a lower alkyl or a lower trifluoroalkyl group, R3 is a hydrogen atom, a lower alkyl group, an alkenyl group, an alkynyl group or a phenyl group, which phenyl group could optionally be substituted by one or more of fluoro, chloro, bromo, trifluoromethyl, methyl, ethyl, methoxy or ethoxy in the ortho, meta or para positions, or optionally substituted by methylenedioxy, provided that at least one of Z1, Z2 and Z3 is a group OR4 and further provided that when Z2 is OH or NH2, Z' is NR24, NHR4, SH, SR4 or OR' or a physiologically acceptable salt or optical isomer thereof, intermediates and methods for their preparation, pharmaceutical preparations containing the compounds and methods for their therapeutical use.

  式中具有治疗活性的新型化合物 式中 Z，为 Z1、Z2 或 Z3，相同或不同，选自 OH、OR'、NH2、NR24、NHR'、SH、SR4 和 OR4 其中 R'为甲酰基、酰基、烷氧羰基或单烷基或二烷基氨基甲酰基，R4 为低级烷基、 R2 是氢、卤素、低级烷基或低级三氟烷基、 R3是氢原子、低级烷基、烯基、炔基或苯基，其中苯基可选择在正位、偏位或对位被氟、氯、溴、三氟甲基、甲基、乙基、甲氧基或乙氧基中的一个或多个取代，或可选择被亚甲基二氧基取代、条件是 Z1、Z2 和 Z3 中至少有一个是 OR4 基团，进一步条件是当 Z2 是 OH 或 NH2 时，Z'是 NR24、NHR4、SH、SR4 或 OR'或其生理上可接受的盐或光学异构体、中间体及其制备方法、含有这些化合物的药物制剂及其治疗使用方法。
• US5240957A
  申请人：——

  公开号：US5240957A

  公开（公告）日：1993-08-31
• Pivaloyl-directed regioselective syntheses of 2,3,6-trioxygenated benzamides: phenolic metabolites of remoxipride
  作者：Stefan Bengtsson、Thomas Hoegberg

  DOI：10.1021/jo00065a015

  日期：1993.6

  The regioselective syntheses of (S)-5-bromo-2,6-dimethoxy-N-[(1-ethyl-2-pyrrolidinyl)methyl]-3-hydroxybenzamide (2) and (S)-5-bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-3-hydroxy-6-methoxy-salicylamide (3) from 2,6-dimethoxybenzoic acid and 4-methoxycatechol are described. The latter compound was protected and ortho-lithiated to introduce the carboxyl function in a regioselective manner. Regiocontrol in bromination and demethylation was achieved by introduction of a bulky pivaloyl group. This strategy also enabled the use of a common intermediate as an alternative synthesis of the catechol 3.