(S )-2-(2-bromo-4,5-dimethoxybenzylamino)-3-phenyl-propan-1-ol | 406951-73-3

• 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: (S )-2-(2-bromo-4,5-dimethoxybenzylamino)-3-phenyl-propan-1-ol
• CAS: 406951-73-3
• 化学式: C₁₈H₂₂BrNO₃
• 分子量: 380.282
• InChiKey: VDQGDCDXQUFKEO-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.72
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S )-2-(2-bromo-4,5-dimethoxybenzylamino)-3-phenyl-propan-1-ol 在 甲酸 、 叔丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 氯仿 、 水 为溶剂， 反应 5.5h， 生成 (S)-11-benzyl-5,6-dimethoxy-10-methyl-2,2-diphenyl-13-oxa-10-aza-2-silatricyclo[13.4.0.0.0^3,8]nonadeca-1(15),3,5,7,16,18-hexaene
  参考文献：
  名称：

  Diversity-Oriented Synthesis of Biaryl-Containing Medium Rings Using a One Bead/One Stock Solution Platform

  摘要：

  Diversity-oriented synthesis of structurally complex and diverse small molecules can be used as the first step in a process to explore cellular and organismal pathways. The success of this process is likely going to be dependent on advances in the synthesis of small molecules having natural product-like structures in an efficient and stereoselective manner. The development, scope, and mechanism of the oxidation of organocuprates was investigated and exploited in the atropdiastereoselective synthesis of biaryl-containing medium rings (9-, 10-, and 11-membered rings). The methodology was performed on high-capacity, large polystyrene beads by metalating aryl bromides with i-PrBu2MgLi, followed by transmetalating with CuCN.2LiBr and then oxidizing with 1,3-dinitrobenzene, and was used in a diversity-oriented synthesis of biaryl-containing medium rings (library total theoretical maximum 1412 members). The high capacity beads were arrayed into 384-well plates and, using a process optimized during the development of a one bead/one stock solution technology platform, converted into arrays of stock solutions, with each stock solution containing largely one compound. These stock solutions were used in numerous phenotypic and protein-binding assays. The process described outlines a pathway that we feel will contribute to a comprehensive and systematic chemical approach to exploring biology (chemical genetics).

  DOI：

  10.1021/ja017248o
• 作为产物：
  描述：

  6-溴藜芦醛 、 L-苯丙氨醇 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以87%的产率得到(S )-2-(2-bromo-4,5-dimethoxybenzylamino)-3-phenyl-propan-1-ol
  参考文献：
  名称：

  Diversity-Oriented Synthesis of Biaryl-Containing Medium Rings Using a One Bead/One Stock Solution Platform

  摘要：

  Diversity-oriented synthesis of structurally complex and diverse small molecules can be used as the first step in a process to explore cellular and organismal pathways. The success of this process is likely going to be dependent on advances in the synthesis of small molecules having natural product-like structures in an efficient and stereoselective manner. The development, scope, and mechanism of the oxidation of organocuprates was investigated and exploited in the atropdiastereoselective synthesis of biaryl-containing medium rings (9-, 10-, and 11-membered rings). The methodology was performed on high-capacity, large polystyrene beads by metalating aryl bromides with i-PrBu2MgLi, followed by transmetalating with CuCN.2LiBr and then oxidizing with 1,3-dinitrobenzene, and was used in a diversity-oriented synthesis of biaryl-containing medium rings (library total theoretical maximum 1412 members). The high capacity beads were arrayed into 384-well plates and, using a process optimized during the development of a one bead/one stock solution technology platform, converted into arrays of stock solutions, with each stock solution containing largely one compound. These stock solutions were used in numerous phenotypic and protein-binding assays. The process described outlines a pathway that we feel will contribute to a comprehensive and systematic chemical approach to exploring biology (chemical genetics).

  DOI：

  10.1021/ja017248o