1-(3,4-dimethylphenyl)-3-dimethyl(ethyl)silyl-2-propyn-1-ol | 882051-33-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3,4-dimethylphenyl)-3-dimethyl(ethyl)silyl-2-propyn-1-ol
• 英文别名: 1-(3,4-Dimethylphenyl)-3-[ethyl(dimethyl)silyl]prop-2-yn-1-ol
• CAS: 882051-33-4
• 化学式: C₁₅H₂₂OSi
• 分子量: 246.425
• InChiKey: PKHBCOLVNCSFAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  1-(3,4-dimethylphenyl)-3-dimethyl(ethyl)silyl-2-propyn-1-ol 在 氢氧化钾 、 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 (R,R)-(OMe)2-(PPh₂)2-1,1';3',3'';1'',1'''-(naphthyl)4 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (S)-3-(Ethyl-dimethyl-silanyl)-5,6-dimethyl-indan-1-one 、 (R)-3-(Ethyl-dimethyl-silanyl)-5,6-dimethyl-indan-1-one
  参考文献：
  名称：

  Rhodium-Catalyzed Asymmetric Synthesis of Indanones:  Development of a New “Axially Chiral” Bisphosphine Ligand

  摘要：

  A rhodium-catalyzed asymmetric isomerization of racemic alpha-arylpropargyl alcohols to beta-chiral indanones has been developed. High enantioselectivity has been realized by the use of a newly developed axially chiral bisphosphine ligand. This ligand is unique in the sense that its axial chirality is fixed to a single configuration upon complexation to a transition metal due to other chiral axes existing within the same molecule.

  DOI：

  10.1021/ja056584s
• 作为产物：
  描述：

  Ethyl-dimethyl-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-silane 在 sodium acetate 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 1-(3,4-dimethylphenyl)-3-dimethyl(ethyl)silyl-2-propyn-1-ol
  参考文献：
  名称：

  Rhodium-Catalyzed Asymmetric Synthesis of Indanones:  Development of a New “Axially Chiral” Bisphosphine Ligand

  摘要：

  A rhodium-catalyzed asymmetric isomerization of racemic alpha-arylpropargyl alcohols to beta-chiral indanones has been developed. High enantioselectivity has been realized by the use of a newly developed axially chiral bisphosphine ligand. This ligand is unique in the sense that its axial chirality is fixed to a single configuration upon complexation to a transition metal due to other chiral axes existing within the same molecule.

  DOI：

  10.1021/ja056584s