2-[2'-tert-butoxycarbonylamino-5'-(4'',4'',5'',5''-tetramethyl-1'',3'',2''-dioxaborolan-2''-yl)-phenyl]-1,3-dithiane | 1007350-93-7

• 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'-tert-butoxycarbonylamino-5'-(4'',4'',5'',5''-tetramethyl-1'',3'',2''-dioxaborolan-2''-yl)-phenyl]-1,3-dithiane
• 英文别名: tert-butyl N-[2-(1,3-dithian-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate
• CAS: 1007350-93-7
• 化学式: C₂₁H₃₂BNO₄S₂
• 分子量: 437.432
• InChiKey: NFQFLQQQAVWMLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 2-[2'-tert-butoxycarbonylamino-5'-(4'',4'',5'',5''-tetramethyl-1'',3'',2''-dioxaborolan-2''-yl)-phenyl]-1,3-dithiane 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.75h， 生成 tert-butyl N-[2-(1,3-dithian-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-N-trimethylsilylcarbamate
  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'-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

文献信息

• High throughput synthesis of diverse 2,5-disubstituted indoles using titanium carbenoids bearing boronate functionality
  作者：Calver A. Main、Hanna M. Petersson、Shahzad S. Rahman、Richard C. Hartley

  DOI：10.1016/j.tet.2007.08.119

  日期：2008.1

  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.