10-hydroxy-9-phospha-10-silatriptycene | 1349171-55-6

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 10-hydroxy-9-phospha-10-silatriptycene
• 英文别名: 8-Hydroxy-1-phospha-8-silapentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaene
• CAS: 1349171-55-6
• 化学式: C₁₈H₁₃OPSi
• 分子量: 304.36
• InChiKey: UIURMIZSCXGTFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.03
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  10-hydroxy-9-phospha-10-silatriptycene 以 二氯甲烷 、 氯仿 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Silica-Supported Triptycene-Type Phosphine. Synthesis, Characterization, and Application to Pd-Catalyzed Suzuki–Miyaura Cross-Coupling of Chloroarenes

  摘要：

  A silica-supported triptycene-type phosphine, Silica-TRIP, comprising a 9-phospha-10-silatriptycene (TRIP) and silica gel as a P-coordination center and a solid support, respectively, was synthesized and structurally characterized by nitrogen absorption measurements and solid-state CP/MAS NMR spectroscopy. Silica-TRIP exhibited a mono-P-ligating feature toward a Pd(II) complex, resulting in selective formation of a 1/1 Pd-P species even with an excess amount of the ligand. As a result, Silica-TRIP enabled Pd-catalyzed Suzuki-Miyaura cross-coupling reactions of chloroarenes under mild conditions, regardless of the moderate electrondonating nature of the triarylphosphine-based ligand.

  DOI：

  10.1021/acscatal.5b00904
• 作为产物：
  描述：

  10-chloro-9-phospha-10-silatriptycene 在 silica gel 作用下， 生成 10-hydroxy-9-phospha-10-silatriptycene
  参考文献：
  名称：

  Rh-Catalyzed Ortho-Selective C–H Borylation of N-Functionalized Arenes with Silica-Supported Bridgehead Monophosphine Ligands

  摘要：

  Supported phosphine-Rh systems, prepared in situ from silica-supported bridgehead monophosphines and [Rh(OH)(cod)]2, have enabled ortho-selective C-H borylation for a range of arenes containing nitrogen-based directing groups. The regioselectivity was excellent with various N-directing groups, including saturated and unsaturated N-heterocycles, tert-aminoalkyl groups, and iminetype C-N double bonds. The reaction showed significant tolerance toward steric repulsion around the reacting C-H bond. This Rh catalysis complements the Jr-catalyzed orthoborylation, which is effective for arenes with oxygen-based directing groups.

  DOI：

  10.1021/ja208364a