2-[2'-amino-5'-(4'',4'',5'',5''-tetramethyl-1'',3'',2''-dioxaborolan-2''-yl)-phenyl]-1,3-dithiane | 1007350-92-6

• 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: 2-[2'-amino-5'-(4'',4'',5'',5''-tetramethyl-1'',3'',2''-dioxaborolan-2''-yl)-phenyl]-1,3-dithiane
• 英文别名: 2-(1,3-Dithian-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
• CAS: 1007350-92-6
• 化学式: C₁₆H₂₄BNO₂S₂
• 分子量: 337.315
• InChiKey: HFSMDZFLCFCHGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  95.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[2'-amino-5'-(4'',4'',5'',5''-tetramethyl-1'',3'',2''-dioxaborolan-2''-yl)-phenyl]-1,3-dithiane 、 二碳酸二叔丁酯 以 四氢呋喃 为溶剂， 反应 36.0h， 以71%的产率得到2-[2'-tert-butoxycarbonylamino-5'-(4'',4'',5'',5''-tetramethyl-1'',3'',2''-dioxaborolan-2''-yl)-phenyl]-1,3-dithiane
  参考文献：
  名称：

  High throughput synthesis of diverse 2,5-disubstituted indoles using titanium carbenoids bearing boronate functionality

  摘要：

  A titanium benzylidene complex bearing a boronate group converted resin-bound esters into enol ethers. Suzuki cross-coupling with aryl iodides followed by cleavage with acid completed the solid-phase synthesis of 2,5-disubstituted N-Boc-indoles. Also reported is the use of tert-butyl lithium and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane to convert an aryl bromide into an arylboronate in the presence of a dithiane, with simultaneous reduction of an aryl azide to an amine. @ 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.119
• 作为产物：
  描述：

  2-(2'-azido-5'-bromophenyl)-1,3-dithiane 、 异丙醇频哪醇硼酸酯 在 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以4.97 g的产率得到2-[2'-amino-5'-(4'',4'',5'',5''-tetramethyl-1'',3'',2''-dioxaborolan-2''-yl)-phenyl]-1,3-dithiane
  参考文献：
  名称：

  High throughput synthesis of diverse 2,5-disubstituted indoles using titanium carbenoids bearing boronate functionality

  摘要：

  A titanium benzylidene complex bearing a boronate group converted resin-bound esters into enol ethers. Suzuki cross-coupling with aryl iodides followed by cleavage with acid completed the solid-phase synthesis of 2,5-disubstituted N-Boc-indoles. Also reported is the use of tert-butyl lithium and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane to convert an aryl bromide into an arylboronate in the presence of a dithiane, with simultaneous reduction of an aryl azide to an amine. @ 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.119

表征谱图