(S)-3-methyl-1-(naphthalen-2-yl)butyl pivalate | 1424035-76-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-3-methyl-1-(naphthalen-2-yl)butyl pivalate
• CAS: 1424035-76-6
• 化学式: C₂₀H₂₆O₂
• 分子量: 298.425
• InChiKey: HQOOWTOKSZDUPP-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  苯硼酸酐 、 (S)-3-methyl-1-(naphthalen-2-yl)butyl pivalate 在 bis(1,5-cyclooctadiene)nickel (0) 、 sodium methylate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以73%的产率得到(S)-2-(3-methyl-1-phenylbutyl)naphthalene
  参考文献：
  名称：

  Nickel-Catalyzed Cross-Couplings of Benzylic Pivalates with Arylboroxines: Stereospecific Formation of Diarylalkanes and Triarylmethanes

  摘要：

  We have developed a stereospecific nickel-catalyzed cross-coupling of benzylic pivalates with arylboroxines. The success of this reaction relies on the use of Ni(cod)(2) as the catalyst and NaOMe as a uniquely effective base. This reaction has broad scope with respect to the arylboroxine and benzylic pivalate, enabling the synthesis of a variety of diarylalkanes and triarylmethanes in good to excellent yields and ee's.

  DOI：

  10.1021/ja312087x
• 作为产物：
  描述：

  3-甲基-1-(萘-2-基)丁烷-1-酮 在 4-二甲氨基吡啶 、 [RhCl2(p-cymene)]2 、 sodium formate 、 三乙胺 、 (1S,2S)-(+)-N-对甲苯磺酰基-1,2-二苯基乙二胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 13.0h， 生成 (S)-3-methyl-1-(naphthalen-2-yl)butyl pivalate
  参考文献：
  名称：

  Nickel-Catalyzed Cross-Couplings of Benzylic Pivalates with Arylboroxines: Stereospecific Formation of Diarylalkanes and Triarylmethanes

  摘要：

  We have developed a stereospecific nickel-catalyzed cross-coupling of benzylic pivalates with arylboroxines. The success of this reaction relies on the use of Ni(cod)(2) as the catalyst and NaOMe as a uniquely effective base. This reaction has broad scope with respect to the arylboroxine and benzylic pivalate, enabling the synthesis of a variety of diarylalkanes and triarylmethanes in good to excellent yields and ee's.

  DOI：

  10.1021/ja312087x

文献信息

• Stereospecific Nickel-Catalyzed Borylation of Secondary Benzyl Pivalates
  作者：R. Martin、R. Martin-Montero、T. Krolikowski、C. Zarate、R. Manzano

  DOI：10.1055/s-0036-1590962

  日期：2017.12

  A stereoselective nickel-catalyzed direct borylation of enantioenriched secondary benzyl pivalates is described. This methodology is characterized by an intriguing cooperativity of simple nickel and copper salts to promote the targeted C–B bond formation under mild reaction conditions. Unlike classical SN2-type processes, this protocol occurs with a neat retention of configuration, resulting in synthetically

  描述了立体选择性镍催化直接硼酸化对映体富集的仲新戊酸苄酯。该方法的特点是简单的镍盐和铜盐具有有趣的协同作用，可在温和的反应条件下促进目标 C-B 键的形成。与经典的 SN2 型工艺不同，该协议以整洁的配置保留发生，从而产生具有优异立体化学保真度的合成通用苄基硼酸酯。