3-溴-2,6-二甲氧基苯甲酰氯 | 84225-91-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-溴-2,6-二甲氧基苯甲酰氯
• 英文名称: 3-bromo-2,6-dimethoxybenzoyl chloride
• 英文别名: Benzoyl chloride, 3-bromo-2,6-dimethoxy-
• CAS: 84225-91-2
• 化学式: C₉H₈BrClO₃
• 分子量: 279.518
• InChiKey: CHIRKTGXHJSREC-UHFFFAOYSA-N

物化性质

• 沸点：
  360.6±42.0 °C(Predicted)
• 密度：
  1.552±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-溴-2,6-二甲氧基苯甲酰氯 在 盐酸 、 三溴化硼 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 30.5h， 生成 3-Bromo-2-hydroxy-6-methoxy-N-(1-propyl-pyrrolidin-2-ylmethyl)-benzamide
  参考文献：
  名称：

  Potential neuroleptic agents. 3. Chemistry and antidopaminergic properties of substituted 6-methoxysalicylamides

  摘要：

  A series of substituted 6-methoxysalicylamides were synthesized from their corresponding 2,6-dimethoxybenzamides by demethylation of one methoxy group with boron tribromide. Substituted 6-methoxysalicylamides having a lipophilic aromatic substituent in the 3-position para with respect to the methoxy group, e.g. a bromo or an iodo atom or an ethyl or a propyl group, and having an (S)-N-(1-alkyl-2-pyrrolidinyl)methyl moiety as the side chain were found to be potent blockers of [3H]spiperone binding in vitro and potent inhibitors of the apomorphine syndrome in the rat. Similar to remoxipride but in contrast to haloperidol, some of the substituted salicylamides show a 10-20-fold separation between the dose that inhibits hyperactivity and that which inhibits stereotypy. It was concluded that, besides the requirement of a lipophilic substituent in the position para to the methoxy group for antidopamine activity in vivo, the formation of a coplanar six-membered pseudoring involving the amide moiety and the methoxy group is a structural requirement for activity in vitro.

  DOI：

  10.1021/jm00147a025
• 作为产物：
  描述：

  2,6-二甲氧基苯甲酸 在 溴 作用下， 以 溶剂黄146 为溶剂， 反应 1.5h， 生成 3-溴-2,6-二甲氧基苯甲酰氯
  参考文献：
  名称：

  Cuyegkeng, Maria Assunta; Mannschreck, Albrecht, Chemische Berichte, 1987, vol. 120, p. 803 - 810

  摘要：

  DOI：

文献信息

• Structure−Activity Relationships of a Series of Substituted Benzamides:  Potent D₂/5-HT₂ Antagonists and 5-HT_1a Agonists as Neuroleptic Agents
  作者：Mark H. Norman、Greg C. Rigdon、William R. Hall、Frank Navas

  DOI：10.1021/jm950551d

  日期：1996.1.1

  A series of substituted (4-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)butyl)benzamide derivatives was prepared and evaluated as potential atypical antipsychotic agents. The target compounds were readily prepared from their benzoyl chloride, benzoic acid, or isatoic anhydride precursors, and they were evaluated in vitro for their ability to bind to dopamine D2, serotonin 5-HT2, and serotonin 5-HT1a

  制备了一系列取代的（4-（4-（1,2-苯并噻唑-3-基）-1-哌嗪基）丁基）苯甲酰胺衍生物，并将其评估为潜在的非典型抗精神病药。目标化合物可以很容易地从其苯甲酰氯，苯甲酸或等位酸酐的前体制备，并在体外评估它们与多巴胺D2、5-羟色胺5-HT2和5-羟色胺5-HT1a受体结合的能力。为了评估这些化合物的潜在抗精神病活性，我们研究了它们在小鼠中抑制阿扑吗啡诱导的爬升反应的能力。进一步评估了选定的化合物，以确定其潜在的副作用。本文讨论了单取代的和多取代的苯甲酰胺的结构-活性关系。尽管几种类似物在体外和体内具有潜在的非典型抗精神病药活性，但蒽环酰胺77（1192U90）的药理作用却十分出色。这项研究的结果是，选择1192U90（2-氨基-N-（4-（4-（1,2-苯并噻唑-3-基）-1-哌嗪基）丁基）苯甲酰胺盐酸盐进行进一步评估。目前正在I期临床试验中，作为一种潜在的非典型抗精神病药。
• Studies on Potential Antiviral Compounds, XXIII. 2-(Substituted benzoylamino)-3,5-dichloropyridines and isosteric benzamides
  作者：Anna Ferranti、Laura Garuti、Giuseppe Giovanninetti、Mariangela Borgatti、Anna Maria Bartoletti

  DOI：10.1002/ardp.19853180114

  日期：——

  Novel 2‐(substituted benzoylamino)‐3,5‐dichloropyridines and isosteric benzamides were synthesized and tested in vitro against the MP strain of herpes simplex virus type 1 [HSV‐1(MP)]. The introduction of methoxy groups at the 2‐ and 6‐positions of the benzoyl moiety yielded compounds which significantly inhibit HSV‐1(MP) growth. Substitution with fluorine at the 4‐position of the benzoyl group resulted

  合成了新型 2-（取代苯甲酰氨基）-3,5- 二氯吡啶和等排苯甲酰胺，并在体外针对单纯疱疹病毒 1 型 [HSV-1 (MP)] MP 株进行了测试。在苯甲酰基部分的 2- 和 6- 位引入甲氧基产生显着抑制 HSV-1 (MP) 生长的化合物。在苯甲酰基的 4-位用氟取代会产生无活性的化合物，总体上会导致细胞毒性增强。2-(3-溴-2,6-二甲氧基苯甲酰氨基)-3,5-二氯吡啶(11)是活性最强的化合物(2.06 log10单位> 99%抑制在100μg/ml)。
• 2-Aminotetralin-derived substituted benzamides with mixed dopamine D2, D3, and serotonin 5-HT1A receptor binding properties: A novel class of potential atypical antipsychotic agents
  作者：Evert J. Homan、Swier Copinga、Lotta Elfström、Trees van der Veen、Jan-Pieter Hallema、Nina Mohell、Lena Unelius、Rolf Johansson、Håkan V. Wikström、Cor J. Grol

  DOI：10.1016/s0968-0896(98)00167-9

  日期：1998.11

  class of potential atypical antipsychotic agents, based on the pharmacological concept of mixed dopamine D2 receptor antagonism and serotonin 5-HT1A receptor agonism, was designed by combining the structural features of the 2-(N,N-di-n-propylamino)tetralins (DPATs) and the 2-pyrrolidinylmethyl-derived substituted benzamides in a structural hybrid. Thus, a series of 35 differently substituted 2-aminotetralin-derived

  通过结合2-（N，N-di-n-propylpropylamino）的结构特征，设计了一种新的化学类潜在的非典型抗精神病药，其基于混合的多巴胺D2受体拮抗作用和血清素5-HT1A受体激动作用的药理学概念结构杂化物中的四氢萘酮（DPAT）和2-吡咯烷基甲基衍生的取代苯甲酰胺。因此，合成了35种不同的2-氨基四氢萘衍生的取代的苯甲酰胺系列，并评估了这些化合物竞争与[3H]-雷氯必利与克隆的人多巴胺D2A和D3受体结合以及[3H] -8的竞争能力。 -OH-DPAT在体外与大鼠血清素5-HT1A受体结合。该系列的先导化合物5-甲氧基-2- [N-（2-苯甲酰胺基乙基）-Nn-丙基氨基]四氢化萘（12a）对多巴胺D2A受体表现出高亲和力（Ki = 3.2 nM），多巴胺D3受体（Ki = 0.58 nM）以及血清素5-HT1A受体（Ki = 0.82 nM）。该系列的结构亲和关系表明，在所有三种受
• Remote Stereocenter through Amide-Directed, Rhodium-Catalyzed Enantioselective Hydroboration of Unactivated Internal Alkenes
  作者：Wei Zhao、Ke-Zhi Chen、An-Zhen Li、Bi-Jie Li

  DOI：10.1021/jacs.2c05993

  日期：2022.7.27

  bioactive molecules, the direct catalytic asymmetric synthesis of this structural motif containing a remote stereocenter remains an important synthetic challenge. Here, we report an amide-directed, rhodium-catalyzed highly diastereo- and enantioselective hydroboration of unactivated internal alkenes. This method provided facile access to enantioenriched amines containing β,γ-vicinal stereocenters. The

  尽管在生物活性分子中经常出现 γ-支链胺，但这种含有远程立体中心的结构基序的直接催化不对称合成仍然是一个重要的合成挑战。在这里，我们报告了一种酰胺定向、铑催化的高度非对映和对映选择性硼氢化反应的未活化内部烯烃。该方法提供了容易获得含有 β,γ-邻位立体中心的对映体富集胺。证明了该策略在生物活性分子合成中的应用。计算研究表明，烯烃迁移插入到氢化铑中控制了对映选择性。
• Potential neuroleptic agents. 2,6-Dialkoxybenzamide derivatives with potent dopamine receptor blocking activities
  作者：Lennart Florvall、Sven Ove Oegren

  DOI：10.1021/jm00353a003

  日期：1982.11

  A series of some novel N-(l-ethyl-2-pyrrolidinylmethyl)benzamides was synthesized and tested for dopamine receptor blockade in vivo by the ability to block the apomorphine syndrome in the rat. Several compounds were considerably more potent than sulpiride as dopamine receptor blockers and displayed low liability to induce extrapyramidal side effects (catalepsy) in the rat. The blockade of dopamine receptor activity in vivo was mainly confined to the levorotatory isomers having the S absolute configuration. The structure-activity relationships are discussed.