(S)-12-benzyl-17,18-dimethoxy-2,2,13-trimethyl-10-oxa-13-aza-2-silatricyclo[13.4.0.0^3,8]nonadeca-1(15),3,7,16,18-hexaene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-12-benzyl-17,18-dimethoxy-2,2,13-trimethyl-10-oxa-13-aza-2-silatricyclo[13.4.0.0^3,8]nonadeca-1(15),3,7,16,18-hexaene
• 英文别名: (12S)-12-benzyl-17,18-dimethoxy-2,2,13-trimethyl-10-oxa-13-aza-2-silatricyclo[13.4.0.03,8]nonadeca-1(19),3,5,7,15,17-hexaene
• 化学式: C₂₈H₃₅NO₃Si
• 分子量: 461.676
• InChiKey: QMKKDJZSHHMXLD-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-溴藜芦醛 在 甲酸 、 叔丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 为溶剂， 反应 5.5h， 生成 (S)-12-benzyl-17,18-dimethoxy-2,2,13-trimethyl-10-oxa-13-aza-2-silatricyclo[13.4.0.0^3,8]nonadeca-1(15),3,7,16,18-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

文献信息

• Towards Diversity-Oriented, Stereoselective Syntheses of Biaryl- or Bis(aryl)metal-Containing Medium Rings
  作者：David R. Spring、Shyam Krishnan、Stuart L. Schreiber

  DOI：10.1021/ja0010507

  日期：2000.6.1

  FT-IR spectrometer with internal referencing. Absorption maxima (νmax) are reported in wavenumbers (cm) and the following abbreviations are used: w, weak; m, medium; s, strong; br, broad. Proton magnetic resonance spectra were recorded on Varian Mercury400 (400MHz), Bruker Avance DMX500 (500MHz), and Varian Unity/Inova500 (500MHz) spectrometers. Proton assignments are supported by H-H COSY, HMQC, NOESY

  实验技术和装置除非另有说明，反应在氩气下用干燥的、新鲜蒸馏的溶剂进行。从钠/二苯甲酮羰基中蒸馏出四氢呋喃。无水 2-甲基四氢呋喃（Aldrich，外消旋）储存在活化的分子筛上。从氢化钙中蒸馏出二氯甲烷。正丁基锂的己烷溶液 (Aldrich) 和叔丁基锂的戊烷溶液 (Aldrich) 在使用前用 1,10 菲咯啉和无水 2-丁醇滴定。所有其他试剂均按照“实验室化学品的纯化”中的说明进行纯化或使用从商业来源获得的。产率是指色谱和光谱纯的化合物。所有反应均通过薄层色谱法 (TLC) 使用预涂有大肠杆菌的玻璃板进行监测。默克硅胶 60 F254 或氧化铝 60 F254。通过紫外荧光猝灭（λmax = 254nm）或用钼酸铈铵或 Dragendorff's 试剂（0.08% w/v 次硝酸铋和 2% w/v KI 的 3M aq. AcOH）染色进行可视化。保留因子 (Rf) 引用为 0.01。熔点是使用
• 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).