(1S,2S)-(2-bromobenzyl)-[2-(2-bromobenzyloxy)-1-methyl-2-phenyl-ethyl]-methylamine

• 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: (1S,2S)-(2-bromobenzyl)-[2-(2-bromobenzyloxy)-1-methyl-2-phenyl-ethyl]-methylamine
• 英文别名: (1S,2S)-1-[(2-bromophenyl)methoxy]-N-[(2-bromophenyl)methyl]-N-methyl-1-phenylpropan-2-amine
• 化学式: C₂₄H₂₅Br₂NO
• 分子量: 503.277
• InChiKey: HJBBVMMHFQCJJG-MHECFPHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1S,2S)-2-[(2-bromo-benzyl)-methyl-amino]-1-phenyl-propan-1-ol 、 2-溴溴苄 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以95%的产率得到(1S,2S)-(2-bromobenzyl)-[2-(2-bromobenzyloxy)-1-methyl-2-phenyl-ethyl]-methylamine
  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

文献信息

• Diversity-Oriented Synthesis of Biaryl-Containing Medium Rings Using a One Bead/One Stock Solution Platform
  作者：David R. Spring、Shyam Krishnan、Helen E. Blackwell、Stuart L. Schreiber

  DOI：10.1021/ja017248o

  日期：2002.2.1

  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).