1-(3,4-methylenedioxyphenyl)-3-dimethyl(ethyl)silyl-2-propyn-1-ol | 882051-34-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1-(3,4-methylenedioxyphenyl)-3-dimethyl(ethyl)silyl-2-propyn-1-ol
• 英文别名: 1-(1,3-Benzodioxol-5-yl)-3-[ethyl(dimethyl)silyl]prop-2-yn-1-ol
• CAS: 882051-34-5
• 化学式: C₁₄H₁₈O₃Si
• 分子量: 262.381
• InChiKey: OHGHQLFHAAAIPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3,4-methylenedioxyphenyl)-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， 以55%的产率得到(S)-8-(Ethyl-dimethyl-silanyl)-7,8-dihydro-1,3-dioxa-as-indacen-6-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：

  3-dimethyl(ethyl)silyl-2-propyn-1-ol 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-(3,4-methylenedioxyphenyl)-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.