(S)-tert-butyl(2-hydroxyphenyl)methylphosphine | 869585-59-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (S)-tert-butyl(2-hydroxyphenyl)methylphosphine
• 英文别名: 2-[Tert-butyl(methyl)phosphanyl]phenol
• CAS: 869585-59-1
• 化学式: C₁₁H₁₇OP
• 分子量: 196.229
• InChiKey: FDOOCWROMGNIKZ-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  (S)-tert-butyl(2-hydroxyphenyl)methylphosphine 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以99%的产率得到(S)-tert-butyl(2-hydroxyphenyl)methylphosphine-borane
  参考文献：
  名称：

  P-Chiral o-Phosphinophenol as a P/O Hybrid Ligand:  Preparation and Use in Cu-Catalyzed Asymmetric Conjugate Addition of Diethylzinc to Acyclic Enones

  摘要：

  (S)-2-(tert-Butylmethylphosphino)phenol and its methyl ether were synthesized from tert-butyldichlorophosphine via optically active phosphine-boranes as the intermediates. The former compound was used as a P/O hybrid ligand in the Cu-catalyzed asymmetric conjugate addition of diethylzinc to acyclic enones to achieve high enantioselectivity of up to 96%.

  DOI：

  10.1021/jo051034y
• 作为产物：
  描述：

  2-(methoxy)methoxyphenylmagnesium bromide 在 tetrafluoroboric acid 、 naphthalen-1-yl-lithium 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 (S)-tert-butyl(2-hydroxyphenyl)methylphosphine
  参考文献：
  名称：

  P-Chiral o-Phosphinophenol as a P/O Hybrid Ligand:  Preparation and Use in Cu-Catalyzed Asymmetric Conjugate Addition of Diethylzinc to Acyclic Enones

  摘要：

  (S)-2-(tert-Butylmethylphosphino)phenol and its methyl ether were synthesized from tert-butyldichlorophosphine via optically active phosphine-boranes as the intermediates. The former compound was used as a P/O hybrid ligand in the Cu-catalyzed asymmetric conjugate addition of diethylzinc to acyclic enones to achieve high enantioselectivity of up to 96%.

  DOI：

  10.1021/jo051034y

文献信息

• P-Chiral <i>o</i>-Phosphinophenol as a P/O Hybrid Ligand:  Preparation and Use in Cu-Catalyzed Asymmetric Conjugate Addition of Diethylzinc to Acyclic Enones
  作者：Yukitoshi Takahashi、Yoshikazu Yamamoto、Kosuke Katagiri、Hiroshi Danjo、Kentaro Yamaguchi、Tsuneo Imamoto

  DOI：10.1021/jo051034y

  日期：2005.10.1

  (S)-2-(tert-Butylmethylphosphino)phenol and its methyl ether were synthesized from tert-butyldichlorophosphine via optically active phosphine-boranes as the intermediates. The former compound was used as a P/O hybrid ligand in the Cu-catalyzed asymmetric conjugate addition of diethylzinc to acyclic enones to achieve high enantioselectivity of up to 96%.