3-(Trimethylsilyl)-1,2-epoxypropan | 16722-11-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: 3-(Trimethylsilyl)-1,2-epoxypropan
• 英文别名: allyltrimethylsilane oxide；Trimethyl[(oxiran-2-yl)methyl]silane；trimethyl(oxiran-2-ylmethyl)silane
• CAS: 16722-11-5
• 化学式: C₆H₁₄OSi
• 分子量: 130.262
• InChiKey: ORXFGAIKYGDKKO-UHFFFAOYSA-N

物化性质

• 沸点：
  112-114 °C
• 密度：
  0.864±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(Trimethylsilyl)-1,2-epoxypropan 在 对硝基苯甲酸 作用下， 以 丙酮 为溶剂， 以50%的产率得到烯丙醇
  参考文献：
  名称：

  Silicon-directed acid ring-opening of allyltrimethylsilane oxide. X-ray structures of 3-triisopropylsilyl-2-(2,4-dinitrobenzoyloxy)-1-propanol and 3-triisopropylsilyl-2-(2,4,6-trinitrobenzoyloxy)-1-propanol

  摘要：

  Allyltrimethylsilane oxide 5 undergoes regiospecific ring-opening with carboxylic acids in chloroform to give the hydroxy esters 6a-e. In polar solvents competing elimination results in the formation of allyl alcohol. Allyltriisopropylsilane oxide 17 undergoes analogous reactions as 5 in chloroform but does not undergo elimination in methanol or acetone. The X-ray structures of 18b and 18c reveal significant lengthening of the C-O (ester) bond (a remarkable 1.502(2) Angstrom for 18c), these structural effects are due to strong sigma(C-Si)-sigma*(C-O) interactions, particularly for 18c. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(98)01002-x
• 作为产物：
  描述：

  烯丙基三甲基硅烷 在 5,10,15,20-tetra(2',6'-dichlorophenyl)porphyrinatoiron(III) chloride 、 1,2,3,4,5-pentafluoro-6-iodosylbenzene 作用下， 以 二氯甲烷 为溶剂， 生成 3-(Trimethylsilyl)-1,2-epoxypropan
  参考文献：
  名称：

  Formation of Both Primary and Secondary N-Alkylhemins during Hemin-Catalyzed Epoxidation of Terminal Alkenes

  摘要：

  The N-alkylhemin formation during iron(III) porphyrin-catalyzed epoxidation of alkenes is studied in a homogeneous system using pentafluoroiodosobenzene (PFIB) as the oxidant. The system is a model for the enzyme cytochrome P-450. A second N-alkyl species other than the well-documented primary N-alkylhemin is observed during the oxidation of terminal alkenes. It is unstable and decomposes under the reaction conditions. It is also a catalyst for alkene epoxidation by PFIB. Its characteristics are consistent with a secondary N-alkylhemin. The kinetics were partially resolved, and rate constants-were estimated for the formation of both N-alkylhemins, for the decomposition of the secondary N-alkylhemin, and for the epoxidation by the hemin and the N-alkylhemins. The partition ratios were measured by a kinetic method, which provides better insight for the mechanisms of both N-alkylation and epoxidation than the measurements by product analysis using heterogeneous systems. We suggest that alkenes reversibly inhibit cytochrome P-450 through the formation of the unstable N-alkylporphyrin species.

  DOI：

  10.1021/ja00106a003

文献信息

• Siliciumorganische verbindungen
  作者：Leonhard Birkofer、Axel Kopp

  DOI：10.1016/0022-328x(84)85135-9

  日期：1984.3
• BIRKOFER, L.;KOPP, A., J. ORGANOMET. CHEM., 1984, 264, N 1-2, 87-98
  作者：BIRKOFER, L.、KOPP, A.

  DOI：——

  日期：——
• Formation of Both Primary and Secondary N-Alkylhemins during Hemin-Catalyzed Epoxidation of Terminal Alkenes
  作者：Zong-Qiang Tian、Joseph L. Richards、Teddy G. Traylor

  DOI：10.1021/ja00106a003

  日期：1995.1

  The N-alkylhemin formation during iron(III) porphyrin-catalyzed epoxidation of alkenes is studied in a homogeneous system using pentafluoroiodosobenzene (PFIB) as the oxidant. The system is a model for the enzyme cytochrome P-450. A second N-alkyl species other than the well-documented primary N-alkylhemin is observed during the oxidation of terminal alkenes. It is unstable and decomposes under the reaction conditions. It is also a catalyst for alkene epoxidation by PFIB. Its characteristics are consistent with a secondary N-alkylhemin. The kinetics were partially resolved, and rate constants-were estimated for the formation of both N-alkylhemins, for the decomposition of the secondary N-alkylhemin, and for the epoxidation by the hemin and the N-alkylhemins. The partition ratios were measured by a kinetic method, which provides better insight for the mechanisms of both N-alkylation and epoxidation than the measurements by product analysis using heterogeneous systems. We suggest that alkenes reversibly inhibit cytochrome P-450 through the formation of the unstable N-alkylporphyrin species.
• Silicon-directed acid ring-opening of allyltrimethylsilane oxide. X-ray structures of 3-triisopropylsilyl-2-(2,4-dinitrobenzoyloxy)-1-propanol and 3-triisopropylsilyl-2-(2,4,6-trinitrobenzoyloxy)-1-propanol
  作者：Fatmir Badali、William Issa、Brett Pool、Jonathan M. White

  DOI：10.1016/s0022-328x(98)01002-x

  日期：1999.3

  Allyltrimethylsilane oxide 5 undergoes regiospecific ring-opening with carboxylic acids in chloroform to give the hydroxy esters 6a-e. In polar solvents competing elimination results in the formation of allyl alcohol. Allyltriisopropylsilane oxide 17 undergoes analogous reactions as 5 in chloroform but does not undergo elimination in methanol or acetone. The X-ray structures of 18b and 18c reveal significant lengthening of the C-O (ester) bond (a remarkable 1.502(2) Angstrom for 18c), these structural effects are due to strong sigma(C-Si)-sigma*(C-O) interactions, particularly for 18c. (C) 1999 Elsevier Science S.A. All rights reserved.