4,4,5,5-Tetramethyl-2-[2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-3-yl]-1,3,2-dioxaborolane | 942070-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 4,4,5,5-Tetramethyl-2-[2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-3-yl]-1,3,2-dioxaborolane
• CAS: 942070-30-6
• 化学式: C₁₇H₂₈B₂O₄S
• 分子量: 350.095
• InChiKey: JGURGLQQJZHJNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  65.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,4,5,5-Tetramethyl-2-[2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-3-yl]-1,3,2-dioxaborolane 在 甲醇 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以72%的产率得到4,4,5,5-四甲基-2-(2-甲基-3-噻吩基)-1,3,2-二氧硼烷
  参考文献：
  名称：

  Harnessing C–H Borylation/Deborylation for Selective Deuteration, Synthesis of Boronate Esters, and Late Stage Functionalization

  摘要：

  Ir-catalyzed deborylation can be used to selectively deuterate aromatic and heteroaromatic substrates. Combined with the selectivities of Ir-catalyzed C-H borylations, uniquely labeled compounds can be prepared. In addition, diborylation/deborylation reactions provide monoborylated regioisomers that complement those prepared by C-H borylation. Comparisons between Ir-catalyzed deborylations and Pd-catalyzed deborylations of diborylated indoles described by Movassaghi are made. The Ir-catalyzed process is more effective for deborylating aromatics and is generally more effective in the monodeborylation of diborylated thiophenes. These processes can be applied to complex molecules such as dopidogrel.

  DOI：

  10.1021/acs.joc.5b01588
• 作为产物：
  描述：

  2-甲基噻吩 、 频那醇硼烷 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 正己烷 为溶剂， 反应 48.0h， 生成 4,4,5,5-Tetramethyl-2-[2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-3-yl]-1,3,2-dioxaborolane
  参考文献：
  名称：

  Harnessing C–H Borylation/Deborylation for Selective Deuteration, Synthesis of Boronate Esters, and Late Stage Functionalization

  摘要：

  Ir-catalyzed deborylation can be used to selectively deuterate aromatic and heteroaromatic substrates. Combined with the selectivities of Ir-catalyzed C-H borylations, uniquely labeled compounds can be prepared. In addition, diborylation/deborylation reactions provide monoborylated regioisomers that complement those prepared by C-H borylation. Comparisons between Ir-catalyzed deborylations and Pd-catalyzed deborylations of diborylated indoles described by Movassaghi are made. The Ir-catalyzed process is more effective for deborylating aromatics and is generally more effective in the monodeborylation of diborylated thiophenes. These processes can be applied to complex molecules such as dopidogrel.

  DOI：

  10.1021/acs.joc.5b01588

文献信息

• Harnessing C–H Borylation/Deborylation for Selective Deuteration, Synthesis of Boronate Esters, and Late Stage Functionalization
  作者：Venkata A Kallepalli、Kristin A. Gore、Feng Shi、Luis Sanchez、Ghayoor A. Chotana、Susanne L. Miller、Robert E. Maleczka、Milton R. Smith

  DOI：10.1021/acs.joc.5b01588

  日期：2015.8.21

  Ir-catalyzed deborylation can be used to selectively deuterate aromatic and heteroaromatic substrates. Combined with the selectivities of Ir-catalyzed C-H borylations, uniquely labeled compounds can be prepared. In addition, diborylation/deborylation reactions provide monoborylated regioisomers that complement those prepared by C-H borylation. Comparisons between Ir-catalyzed deborylations and Pd-catalyzed deborylations of diborylated indoles described by Movassaghi are made. The Ir-catalyzed process is more effective for deborylating aromatics and is generally more effective in the monodeborylation of diborylated thiophenes. These processes can be applied to complex molecules such as dopidogrel.