(M)-6-trimethylsilyl-3,3'-diiodo-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl | 1158868-64-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (M)-6-trimethylsilyl-3,3'-diiodo-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl
• 英文别名: [7-Iodo-5-[3-iodo-2-(methoxymethoxy)naphthalen-1-yl]-6-(methoxymethoxy)naphthalen-2-yl]-trimethylsilane
• CAS: 1158868-64-4
• 化学式: C₂₇H₂₈I₂O₄Si
• 分子量: 698.411
• InChiKey: UCMYAIGMVUSNLI-UHFFFAOYSA-N

物化性质

• 熔点：
  83-87 °C
• 沸点：
  622.3±55.0 °C(predicted)
• 密度：
  1.63±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.38
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (M)-6-trimethylsilyl-3,3'-diiodo-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl 、 5-乙炔基-2-吡啶-2-基吡啶 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 copper(l) iodide 、 1,1'-bis(diphenylphosphino)ferrocene 作用下， 以 四氢呋喃 、 三乙胺 为溶剂， 反应 72.0h， 以90%的产率得到
  参考文献：
  名称：

  Immobilization of Bis(Bipyridine) BINOL Ligands and Their Use in Chiral Resolution

  摘要：

  An enantiomerically pure bis(bipyridine) BINOL ligand was synthesized which was functionalized with an iodine substituent in its periphery. Using this halogen function, the ligand was immobilized on a commercially available polystyrene gel via Suzuki cross-coupling. The functionalized gel was found to be effective in the chiral resolution of similar bis(bipyridine) ligands based on a Troger's base core.

  DOI：

  10.1021/ol901958v
• 作为产物：
  描述：

  (M)-6-trimethylsilyl-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl 在 仲丁基锂 、 碘 作用下， 以 四氢呋喃 、 环己烷 、 环己醇 为溶剂， 反应 3.5h， 以97%的产率得到(M)-6-trimethylsilyl-3,3'-diiodo-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl
  参考文献：
  名称：

  Immobilization of Bis(Bipyridine) BINOL Ligands and Their Use in Chiral Resolution

  摘要：

  An enantiomerically pure bis(bipyridine) BINOL ligand was synthesized which was functionalized with an iodine substituent in its periphery. Using this halogen function, the ligand was immobilized on a commercially available polystyrene gel via Suzuki cross-coupling. The functionalized gel was found to be effective in the chiral resolution of similar bis(bipyridine) ligands based on a Troger's base core.

  DOI：

  10.1021/ol901958v

文献信息

• Self-supported BINOL–Zn catalysts for heterogeneous enantioselective epoxidation of (E)-α,β-unsaturated ketones
  作者：Haiming Wang、Zheng Wang、Kuiling Ding

  DOI：10.1016/j.tetlet.2009.02.151

  日期：2009.5

  A class of chiral self-supported catalysts prepared from bis-BINOL ligands and diethyl zinc were successfully applied in the hetereogeneous enantioselective epoxidation of a range of (E)-alpha,beta-unsaturated ketones, affording the corresponding epoxy ketones in high enantioselectivity. The self-supported catalysts were easily recovered from the reaction mixture and were reusable for several consecutive runs. (C) 2009 Elsevier Ltd. All rights reserved.