1-(溴甲基)-3-甲氧基-2-苯基甲氧基苯 | 58402-40-7

• 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: 1-(溴甲基)-3-甲氧基-2-苯基甲氧基苯
• 英文名称: 2-benzyloxy-3-methoxybenzyl bromide
• 英文别名: 2-(benzyloxy)-1-(bromomethyl)-3-methoxybenzene；Benzene, 1-(bromomethyl)-3-methoxy-2-(phenylmethoxy)-；1-(bromomethyl)-3-methoxy-2-phenylmethoxybenzene
• CAS: 58402-40-7
• 化学式: C₁₅H₁₅BrO₂
• 分子量: 307.187
• InChiKey: AYNKAXMSZZZOKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  380.3±32.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  1-(溴甲基)-3-甲氧基-2-苯基甲氧基苯 在 manganese triacetate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 23.08h， 生成 1-Acetoxy-5-benzyloxy-6-methoxy-2-oxo-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  自由基介导的δ-芳基-β-二羰基化合物环化为β-四氢萘酮[3,4-dihydronaphthalen-2（1 H）-ones]

  摘要：

  在四当量乙酸锰（III）在乙酸中的存在下，芳环中带有电子释放基团的δ-芳基-β-二羰基化合物经过有效的自由基介导的氧化环化反应生成β-四氢萘酮。二次氧化反应总是在最初形成的β-四氢萘酮的苄基α-位上引起乙酰氧基化。使用氧化剂的铈（IV）在甲醇中的硝酸铵得到相应的α-甲氧基化的β-四氢萘酮。在用碱性硅胶处理时，α-乙酰氧基-α-酰基-β-四氢萘酮，而不是它们的α-乙酰氧基-α-烷氧基羰基类似物，以高收率芳香化，从而为适当取代的β-萘酚提供了有效的合成入口。结合先前提出的迈克尔加成机理讨论了δ-芳基β-二酮中间体的这种自由基介导的分子内环状结构可能参与萘类安沙霉素抗生素的第二个碳环的生物合成形成。

  DOI：

  10.1039/p19960002603
• 作为产物：
  描述：

  2-苄氧基-3-甲氧基苯甲醛 在 sodium tetrahydroborate 、 三溴化磷 作用下， 生成 1-(溴甲基)-3-甲氧基-2-苯基甲氧基苯
  参考文献：
  名称：

  迈向EMA401的可扩展综合和过程，第I部分：后期过程开发，路线侦察和ICH M7评估

  摘要：

  我们提出钠（3 S）-5-（苄氧基）-2-（二苯基乙酰基）-6-甲氧基-1,2,3,4-四氢异喹啉-3-羧酸盐（EMA401，olodanrigan），一种血管紧张素II 2型拮抗剂。该手稿的特点是对用于后期临床用品的最终游戏进行了工艺优化，概述了在侦查关键中间体苯丙氨酸衍生物的路线中确定的合成策略，以及潜在形成的剧毒双（双氯甲基）的分析控制策略。 ）醚（BCME）。从苯丙氨酸衍生物开始，我们描述了从早期阶段到后期阶段的最终过程的优化，并因此改善了PMI因子。该序列包括Pictet-Spengler环化和酰胺偶联，这是最后一个形成键的步骤，并且在试点工厂中成功完成了175千克规模的制造过程。修改后的工艺条件消除了第一步羧酸的原位活化，避免了REACH列出的溶剂DMF，并导致PMI改善了3倍。在最终结晶中，在复杂的固体中发现了新的，热力学上更稳定的原料药广泛的多晶型物筛选过程中EMA401的

  DOI：

  10.1021/acs.oprd.0c00215

文献信息

• Two Approaches to the Aromatic Core of the Aminonaphthoquinone Antibiotics
  作者：Christopher C. Nawrat、Leoni I. Palmer、Alexander J. Blake、Christopher J. Moody

  DOI：10.1021/jo400737f

  日期：2013.6.7

  Two complementary approaches are presented for the synthesis of the quinone chromophores of the naphthoquinone ansamycins and related natural products. The first involves the use of an improved protocol for the manganese(III) acetate mediated cyclization of 5-aryl-1,3-dicarbonyl compounds to β-naphthols, leading to the simple, scalable preparation of building blocks suitable for the synthesis of naturally

  提出了两种互补的方法来合成萘醌安沙霉素和相关天然产物的醌发色团。首先涉及使用改进的方案，以乙酸锰（III）介导的5-芳基-1,3-二羰基化合物环化成β-萘酚，从而导致可简单，可扩展地制备适合天然合成的结构单元发生氨基萘醌。第二种方法涉及一系列新的含酯的Danishefsky型二烯与N保护的氨基苯醌的Diels-Alder反应，以更快速地获得相似的中间体。
• Dopaminergic compounds
  申请人：Abbott Laboratories

  公开号：US04994486A1

  公开（公告）日：1991-02-19

  Novel compounds of Formula (I): ##STR1## or pharmaceutically acceptable salts, esters and amides thereof, wherein A is O, C, CH or CH.sub.2, n is 0 or 1, and the dotted line is a single bond when A is O or CH.sub.2 and a double bond when A is CH or when n=0, A is C and R.sub.6 and A taken together form a nitrogen-containing heterocycle; R is hydrogen, lower alkyl or a readily cleavable group; R.sub.1 is selected from hydrogen, halogen, lower alkyl, haloalkyl and lower alkoxy; R.sub.2 is selected from hydrogen, halogen, lower alkyl and haloalkyl or, taken together with R.sub.8, forms a fused ring; R.sub.3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl or arylalkyl or, taken together with R.sub.4, forms a spirocycloalkyl or, taken together with R.sub.5, forms a fused cycloalkyl; R.sub.4 is hydrogen or alkyl or, taken together with R.sub.3, forms a spirocycloalkyl; R.sub.5 is hydrogen or alkyl or, taken together with R.sub.3, forms a fused cycloalkyl; R.sub.6 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or arylalkyl or, taken together with A when A is C and when n is 0, forms a fused nitrogen-containing heterocycle or, taken together with R.sub.7 or R.sub.8, forms a nitrogen-containing heterocycle; R.sub.7 is hydrogen or alkyl or, taken together with R.sub.6 or R.sub.8, forms a nitrogen-containing heterocycle; R.sub.8 is hydrogen or alkyl or, taken together with R.sub.6 or R.sub.7, forms a nitrogen-containing heterocycle or, taken together with R.sub.2, forms a fused ring, with the proviso that R.sub.3 and R.sub.4 cannot simultaneously both be hydrogen, are selective dopaminergic agents and are useful for treating disorders characterized by abnormal dopaminergic activity in the central or the peripheral nervous system, for example, neurological disorders such as psychoses, Parkinson's Disease, certain cardiovascular disorders and addictive behavior disorders.

  化合物的化学式（I）的新颖化合物：##STR1##或其药学上可接受的盐、酯和酰胺，其中A为O、C、CH或CH.sub.2，n为0或1，虚线是当A为O或CH.sub.2时为单键，当A为CH或n=0时为双键，当A为C且R.sub.6和A一起形成含氮杂环时，R为氢、低碳烷基或易解离基团；R.sub.1选择自氢、卤素、低碳烷基、卤代烷基和低烷氧基；R.sub.2选择自氢、卤素、低碳烷基和卤代烷基或与R.sub.8一起形成融合环；R.sub.3为氢、烷基、烯基、炔基、环烷基、芳基或芳基烷基或与R.sub.4一起形成螺环烷基或与R.sub.5一起形成融合环烷基；R.sub.4为氢或烷基或与R.sub.3一起形成螺环烷基；R.sub.5为氢或烷基或与R.sub.3一起形成融合环烷基；R.sub.6为氢、烷基、烯基、炔基、环烷基或芳基烷基或与A一起形成融合含氮杂环或与R.sub.7或R.sub.8一起形成含氮杂环；R.sub.7为氢或烷基或与R.sub.6或R.sub.8一起形成含氮杂环；R.sub.8为氢或烷基或与R.sub.6或R.sub.7一起形成含氮杂环或与R.sub.2一起形成融合环，但R.sub.3和R.sub.4不能同时都是氢，是选择性多巴胺能作用剂，用于治疗中枢或外周神经系统中存在异常多巴胺能活性的疾病，例如，神经症、帕金森病、某些心血管疾病和成瘾行为障碍。
• Synthesis and pharmacological evaluation of 1-(aminomethyl)-3,4-dihydro-5-hydroxy-1H-2-benzopyrans as dopamine D1 selective ligands
  作者：Michael R. Michaelides、Robert Schoenleber、Sheela Thomas、Diane M. Yamamoto、Donald R. Britton、Robert MacKenzie、John W. Kebabian

  DOI：10.1021/jm00114a002

  日期：1991.10

  A series of 3-substituted 1-(aminomethyl)-3,4-dihydro-5-hydroxy-1H-2- benzopyrans were prepared as potential D1 selective antagonists. The compounds were evaluated for their affinity and selectivity for the D1 receptor as well as for their functional antagonism of D1-mediated pharmacological events. The compounds show potent D1 antagonist properties in vitro. The optimum nitrogen substitution was found

  制备了一系列3-取代的1-（氨基甲基）-3，4-二氢-5-羟基-1H-2-苯并吡喃，作为潜在的D1选择性拮抗剂。评价化合物对D1受体的亲和力和选择性，以及对D1介导的药理作用的功能拮抗作用。这些化合物在体外显示出有效的D1拮抗剂特性。发现最佳的氮取代是伯胺，并且观察到的在6-位取代的效力的顺序是OH大于Br大于H大于OMe。还对体内的两种代表性化合物（6-甲基和6-溴类似物）的多巴胺能活性进行了评估。有趣的是，两种化合物均表现为有效的体内激动剂。
• Asymmetric Phase-Transfer Alkylation of Readily Available Aryl Aldehyde Schiff Bases of Amino Acid Ethyl Esters
  作者：Jinying Lu、Lei Huang、Huatai Liang、Zhe Wang、Terumasa Kato、Yan Liu、Keiji Maruoka

  DOI：10.1021/acs.orglett.3c04290

  日期：——

  Asymmetric phase-transfer alkylation of the N-(arylmethylene)-α-alkylamino acid ethyl esters and N-(arylmethylene)glycine ethyl esters was found to be catalyzed by the (R)- or (S)-Simplified Maruoka Catalyst with high efficiency and excellent enantioselectivity. This approach was successfully applied to the enantioselective formal synthesis of the angiotensin II type 2 receptor (AT2R) antagonists Olodanrigan

  ( R )-或( S )-简化Maruoka催化剂高效催化N- (芳基亚甲基)-α-烷基氨基酸乙酯和N- (芳基亚甲基)甘氨酸乙酯的不对称相转移烷基化和优异的对映选择性。该方法成功应用于血管紧张素II 2型受体（AT2R）拮抗剂Olodanrigan和LX9211的对映选择性形式合成，并通过LX9211合成关键中间体的公斤级合成证明了其实用性。
• Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential
  作者：Yogesh Kanekar、Khalander Basha、Sharad Duche、Rajan Gupte、Arnab Kapat

  DOI：10.1016/j.ejmech.2013.06.016

  日期：2013.9

  Regioselective synthesis of 9,10-Dihydro-2,5-Dimethoxyphenanthrene-1,7-diol (1) and 9,10-Dihydro-2,7-Dimethoxyphenanthrene-1,5-diol (2) was achieved using regioselective methylation, Wittig reaction, intramolecular cyclization and hydrogenation as key steps. The synthesis was successfully completed in total of 15 steps with 3.3% overall yield in case of 1 and in total of 13 steps with 9.0% overall yield in case of 2. All compounds (1-4) showed good antioxidant and anti-inflammatory activity in in vitro assays and these activities were found to be due the presence of phenolic hydroxyl groups. (C) 2013 Elsevier Masson SAS. All rights reserved.