(R)-2-methyl-N-[(R)-naphthalen-2-yl-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]propane-2-sulfinamide | 1426585-74-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2-methyl-N-[(R)-naphthalen-2-yl-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]propane-2-sulfinamide
• CAS: 1426585-74-1
• 化学式: C₂₁H₃₀BNO₃S
• 分子量: 387.351
• InChiKey: IGYZAMBYFAAXDX-XRHLQHRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-2-methyl-N-[(R)-naphthalen-2-yl-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]propane-2-sulfinamide 在 盐酸 、 甲醇 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Improving Carbene–Copper-Catalyzed Asymmetric Synthesis of α-Aminoboronic Esters Using Benzimidazole-Based Precursors

  摘要：

  By using a benzimidazole core and N-substitutions to tune the electronic properties of the corresponding N-heterocyclic carbenes, a one-pot protocol for efficient synthesis of alpha-aminoboronic esters without the need of a glovebox was developed in this work. The starting materials for the transformation can also be extended from aldehydes to ketones. An alternative protocol with short reaction time using preformed carbene-copper chloride is also described.

  DOI：

  10.1021/jo4000477
• 作为产物：
  描述：

  (R)-2-methyl-N-(naphthalen-2-ylmethylene)propane-2-sulfinamide 、 联硼酸频那醇酯 在 C₂₇H₁₈ClCuN₂ 、 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以83%的产率得到(R)-2-methyl-N-[(R)-naphthalen-2-yl-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]propane-2-sulfinamide
  参考文献：
  名称：

  Improving Carbene–Copper-Catalyzed Asymmetric Synthesis of α-Aminoboronic Esters Using Benzimidazole-Based Precursors

  摘要：

  By using a benzimidazole core and N-substitutions to tune the electronic properties of the corresponding N-heterocyclic carbenes, a one-pot protocol for efficient synthesis of alpha-aminoboronic esters without the need of a glovebox was developed in this work. The starting materials for the transformation can also be extended from aldehydes to ketones. An alternative protocol with short reaction time using preformed carbene-copper chloride is also described.

  DOI：

  10.1021/jo4000477

文献信息

• Improving Carbene–Copper-Catalyzed Asymmetric Synthesis of α-Aminoboronic Esters Using Benzimidazole-Based Precursors
  作者：Kun Wen、Han Wang、Jinbo Chen、He Zhang、Xiaodan Cui、Chao Wei、Erkang Fan、Zhihua Sun

  DOI：10.1021/jo4000477

  日期：2013.4.5

  By using a benzimidazole core and N-substitutions to tune the electronic properties of the corresponding N-heterocyclic carbenes, a one-pot protocol for efficient synthesis of alpha-aminoboronic esters without the need of a glovebox was developed in this work. The starting materials for the transformation can also be extended from aldehydes to ketones. An alternative protocol with short reaction time using preformed carbene-copper chloride is also described.