(S)-pinacol(1-(5-nitro-6-methoxy-2-naphthylethyl))boronate | 748801-47-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-pinacol(1-(5-nitro-6-methoxy-2-naphthylethyl))boronate
• 英文别名: 2-[(1S)-1-(6-methoxy-5-nitronaphthalen-2-yl)ethyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 748801-47-0
• 化学式: C₁₉H₂₄BNO₅
• 分子量: 357.214
• InChiKey: MMVABOOONCOZHQ-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  73.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-pinacol(1-(5-nitro-6-methoxy-2-naphthylethyl))boronate 在 sodium hydroxide 、 双氧水 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 (S)-1-(5-nitro-6-methoxy-2-naphthyl)ethanol
  参考文献：
  名称：

  Regio- and Enantiocontrol in the Room-Temperature Hydroboration of Vinyl Arenes with Pinacol Borane

  摘要：

  The catalyzed hydroboration of vinyl arenes was carried out using pinacol borane instead of catechol borane, as the former reagent and the product boronates are significantly easier to handle. By careful choice of catalyst, either the branched or the linear product can be obtained in greater than 96% selectivity. Interestingly, common ligands such as BINAP and Josiphos give opposite asymmetric induction with pinacol borane as compared with catechol borane, while P,N-ligands such as Quinap gave the same sense of induction. The hydroboration of 6-methoxynaphthalene proceeded with the greatest regio- (95:5) and enantioselectivity (94:6) of all vinyl arenes examined. The hydroboration product was then employed in a concise synthesis of the nonsteroidal antiinflammatory agent, Naproxen.

  DOI：

  10.1021/ja049761i
• 作为产物：
  描述：

  5-nitro-6-methoxy-2-bromonaphthalene 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 (R,R(Fc))-1-diphenylphosphino-2-(1-dicyclohexylphosphinoethyl)ferrocene 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 (S)-pinacol(1-(5-nitro-6-methoxy-2-naphthylethyl))boronate
  参考文献：
  名称：

  Regio- and Enantiocontrol in the Room-Temperature Hydroboration of Vinyl Arenes with Pinacol Borane

  摘要：

  The catalyzed hydroboration of vinyl arenes was carried out using pinacol borane instead of catechol borane, as the former reagent and the product boronates are significantly easier to handle. By careful choice of catalyst, either the branched or the linear product can be obtained in greater than 96% selectivity. Interestingly, common ligands such as BINAP and Josiphos give opposite asymmetric induction with pinacol borane as compared with catechol borane, while P,N-ligands such as Quinap gave the same sense of induction. The hydroboration of 6-methoxynaphthalene proceeded with the greatest regio- (95:5) and enantioselectivity (94:6) of all vinyl arenes examined. The hydroboration product was then employed in a concise synthesis of the nonsteroidal antiinflammatory agent, Naproxen.

  DOI：

  10.1021/ja049761i

文献信息

• Regio- and Enantiocontrol in the Room-Temperature Hydroboration of Vinyl Arenes with Pinacol Borane
  作者：Cathleen M. Crudden、Yonek B. Hleba、Austin C. Chen

  DOI：10.1021/ja049761i

  日期：2004.8.1

  The catalyzed hydroboration of vinyl arenes was carried out using pinacol borane instead of catechol borane, as the former reagent and the product boronates are significantly easier to handle. By careful choice of catalyst, either the branched or the linear product can be obtained in greater than 96% selectivity. Interestingly, common ligands such as BINAP and Josiphos give opposite asymmetric induction with pinacol borane as compared with catechol borane, while P,N-ligands such as Quinap gave the same sense of induction. The hydroboration of 6-methoxynaphthalene proceeded with the greatest regio- (95:5) and enantioselectivity (94:6) of all vinyl arenes examined. The hydroboration product was then employed in a concise synthesis of the nonsteroidal antiinflammatory agent, Naproxen.