1-(3,4-dimethoxyphenyl)-2-bromopropan-1-ol | 4962-37-2

• 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: 1-(3,4-dimethoxyphenyl)-2-bromopropan-1-ol
• 英文别名: 2-Brom-1-(3,4-dimethoxy-phenyl)-propan-1-ol；1-(3,4-Dimethoxy-phenyl)-2-brom-propanol；1-(3,4-Dimethoxy-phenyl)-1-hydroxy-2-brom-propan；2-bromo-1-(3,4-dimethoxy-phenyl)-propan-1-ol；1²-Brom-1¹-oxy-3.4-dimethoxy-1-propyl-benzol；β-Brom-α-oxy-α-(3.4-dimethoxy-phenyl)-propan；2-Brom-1-oxy-1-(3.4-dimethoxy-phenyl)-propan；Isoeugenolmethylaether-bromhydrin；2-Bromo-1-(3,4-dimethoxyphenyl)propan-1-ol
• CAS: 4962-37-2
• 化学式: C₁₁H₁₅BrO₃
• 分子量: 275.142
• InChiKey: SPFXCJOKSNXTEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3,4-dimethoxyphenyl)-2-bromopropan-1-ol 在 甲醇 、 sodium 作用下， 反应 2.5h， 以0.42 g的产率得到1-(3,4-dimethoxyphenyl)-1,2-epoxypropane
  参考文献：
  名称：

  Troponoids. 7. Chemistry and dopamine agaonist activity of ciladopa and related aralkyltroponylpiperazines

  摘要：

  A series of N-aralkyltroponylpiperazine derivatives were synthesized and evaluated for dopaminergic activity in rats rendered hypokinetic by the bilateral injection of 6-hydroxydopamine (6-OHDA) into the anterolateral hypothalamus. Several members of the series were active, and a structure-activity relationship is presented. A few selected compounds were also evaluated with regard to their ability to induce contralateral rotational behavior in rats with a unilateral 6-OHDA-induced lesion of the nigrostriatal dopamine (DA) pathway and to suppress elevated serum prolactin levels. The compounds were compared to bromocriptine. Some of the more potent analogues were also assayed for their binding affinity to dopamine (DA) and alpha 1-adrenergic receptors. The results established that the potency of some of the compounds were comparable or superior to that of bromocriptine indicated that potent dopaminergic activity was dependent on the presence of both a substituted phenyl and a troponylpiperazine moiety, and confirmed that the dopaminergic activity depends on relative and absolute stereochemistry.

  DOI：

  10.1021/jm00152a004
• 作为产物：
  描述：

  2-溴-3-4-二甲氧基苯丙酮 在 sodium tetrahydroborate 作用下， 以 甲醇 、 氯仿 为溶剂， 以1.4 g的产率得到1-(3,4-dimethoxyphenyl)-2-bromopropan-1-ol
  参考文献：
  名称：

  Troponoids. 7. Chemistry and dopamine agaonist activity of ciladopa and related aralkyltroponylpiperazines

  摘要：

  A series of N-aralkyltroponylpiperazine derivatives were synthesized and evaluated for dopaminergic activity in rats rendered hypokinetic by the bilateral injection of 6-hydroxydopamine (6-OHDA) into the anterolateral hypothalamus. Several members of the series were active, and a structure-activity relationship is presented. A few selected compounds were also evaluated with regard to their ability to induce contralateral rotational behavior in rats with a unilateral 6-OHDA-induced lesion of the nigrostriatal dopamine (DA) pathway and to suppress elevated serum prolactin levels. The compounds were compared to bromocriptine. Some of the more potent analogues were also assayed for their binding affinity to dopamine (DA) and alpha 1-adrenergic receptors. The results established that the potency of some of the compounds were comparable or superior to that of bromocriptine indicated that potent dopaminergic activity was dependent on the presence of both a substituted phenyl and a troponylpiperazine moiety, and confirmed that the dopaminergic activity depends on relative and absolute stereochemistry.

  DOI：

  10.1021/jm00152a004

文献信息

• Water-promoted cascade synthesis of α-arylaldehydes from arylalkenes using N-halosuccinimides: an avenue for asymmetric oxidation using Cinchona organocatalysis
  作者：Abhishek Sharma、Naina Sharma、Rakesh Kumar、Upendra K. Sharma、Arun K. Sinha

  DOI：10.1039/b908717f

  日期：——

  The direct oxidation of arylalkenes into α-arylaldehydes is achieved for the first time in water without relying on transition metal catalysts, and a novel organocatalytic enantioselective approach is also explored to provide up to 30% ee in initial investigations.

  首次在水中直接将芳基烯烃氧化为α-芳基醛，而无需依赖过渡金属催化剂。此外，还探索了一种新颖的有机催化剂手性选择性方法，在初步研究中可实现最高30%的外消旋过量。
• Mannich, Archiv der Pharmazie, 1910, vol. 248, p. 143
  作者：Mannich

  DOI：——

  日期：——
• Mannich; Jacobsohn, Chemische Berichte, 1910, vol. 43, p. 193
  作者：Mannich、Jacobsohn

  DOI：——

  日期：——
• Mannich; Schmitt, Archiv der Pharmazie, 1928, p. 80
  作者：Mannich、Schmitt

  DOI：——

  日期：——
• Mannich, Chemisches Zentralblatt, 1909, vol. 80, # I, p. 924
  作者：Mannich

  DOI：——

  日期：——