(S)-1-phenyl-3-dimethyl(ethyl)silyl-2-propyn-1-ol | 882051-43-6

• 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: (S)-1-phenyl-3-dimethyl(ethyl)silyl-2-propyn-1-ol
• 英文别名: (1S)-3-[ethyl(dimethyl)silyl]-1-phenylprop-2-yn-1-ol
• CAS: 882051-43-6
• 化学式: C₁₃H₁₈OSi
• 分子量: 218.371
• InChiKey: HIUZVXMQRNTPQJ-CYBMUJFWSA-N

物化性质

• 沸点：
  299.2±28.0 °C(Predicted)
• 密度：
  0.983±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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)-1-phenyl-3-dimethyl(ethyl)silyl-2-propyn-1-ol 在 氢氧化钾 、 lithium aluminium tetrahydride 、 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 (R,R)-(OMe)2-(PPh₂)2-1,1';3',3'';1'',1'''-(naphthyl)4 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 27.5h， 生成 R-(-)-1-茚酚
  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：

  2-((S)-1-Phenyl-prop-2-ynyloxy)-tetrahydro-pyran 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 15.0h， 生成 (S)-1-phenyl-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

文献信息

• Rhodium-Catalyzed Asymmetric Synthesis of Indanones:  Development of a New “Axially Chiral” Bisphosphine Ligand
  作者：Ryo Shintani、Keiji Yashio、Tomoaki Nakamura、Kazuhiro Okamoto、Toyoshi Shimada、Tamio Hayashi

  DOI：10.1021/ja056584s

  日期：2006.3.1

  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.