tert-butyl-[2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethoxy]-dimethylsilane | 1240036-33-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl-[2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethoxy]-dimethylsilane
• CAS: 1240036-33-2
• 化学式: C₁₃H₂₈O₃Si
• 分子量: 260.449
• InChiKey: WNRJWIACHSQFRE-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl-[2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethoxy]-dimethylsilane 在 indium(III) triflate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.08h， 以96%的产率得到(2R)-4-[tert-butyl(dimethyl)silyl]oxybutane-1,2-diol
  参考文献：
  名称：

  Mild, versatile, and chemoselective indium(III) triflate-catalyzed deprotection of acetonides under microwave heating conditions

  摘要：

  A series of acetonides (both terminal and internal isopropylidene acetals) have been deprotected under catalytic, neutral conditions to give their corresponding 1,2-diols. The reactions utilize indium(III) triflate in the presence of water and an organic solvent with mild microwave heating. Terminal acetonides are chemoselectivley removed in the presence of internal acetonides; acid labile functional groups remain intact under these conditions, thereby greatly enhancing the scope of the reaction substrates that can be utilized with this approach. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.116
• 作为产物：
  描述：

  (3-丁烯-1-基氧基)(二甲基)(2-甲基-2-丙基)硅烷 在 Pt(dba)2 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.5h， 生成 tert-butyl-[2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethoxy]-dimethylsilane
  参考文献：
  名称：

  站点选择性和立体定向级联Suzuki-Miyaura环烷基1,2-双硼酸酯和2,2'-二卤代1,1'-联芳基的环

  摘要：

  已开发出可产生9,10-二氢菲的级联铃木-宫浦交叉偶联剂。使用具有不对称取代模式的联芳基，观察到全位点选择性。此外，烷基1,2-双硼烷频哪醇酯的这种交叉偶联通过具有完整立体保留的仲硼酸酯的挑战性偶联而进行。

  DOI：

  10.1039/d1cc00648g

文献信息

• A site-selective and stereospecific cascade Suzuki–Miyaura annulation of alkyl 1,2-bisboronic esters and 2,2′-dihalo 1,1′-biaryls
  作者：Suzanne Willems、Georgios Toupalas、Julia C. Reisenbauer、Bill Morandi

  DOI：10.1039/d1cc00648g

  日期：——

  A cascade Suzuki–Miyaura cross-coupling giving rise to 9,10-dihydrophenanthrenes has been developed. Using biaryls with unsymmetrical substitution-pattern full site-selectivity was observed. Furthermore, this cross-coupling of an alkyl 1,2-bisboronic pinacol ester proceeds through the challenging coupling of a secondary boronate with complete stereoretention.

  已开发出可产生9,10-二氢菲的级联铃木-宫浦交叉偶联剂。使用具有不对称取代模式的联芳基，观察到全位点选择性。此外，烷基1,2-双硼烷频哪醇酯的这种交叉偶联通过具有完整立体保留的仲硼酸酯的挑战性偶联而进行。
• Mild, versatile, and chemoselective indium(III) triflate-catalyzed deprotection of acetonides under microwave heating conditions
  作者：Kathryn C. Golden、Brian T. Gregg、John F. Quinn

  DOI：10.1016/j.tetlet.2010.05.116

  日期：2010.8

  A series of acetonides (both terminal and internal isopropylidene acetals) have been deprotected under catalytic, neutral conditions to give their corresponding 1,2-diols. The reactions utilize indium(III) triflate in the presence of water and an organic solvent with mild microwave heating. Terminal acetonides are chemoselectivley removed in the presence of internal acetonides; acid labile functional groups remain intact under these conditions, thereby greatly enhancing the scope of the reaction substrates that can be utilized with this approach. (C) 2010 Elsevier Ltd. All rights reserved.