2-Methyl-2-[2-(2-trimethylsilanyl-ethoxy)-allyl]-malonic acid diethyl ester | 207673-91-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-Methyl-2-[2-(2-trimethylsilanyl-ethoxy)-allyl]-malonic acid diethyl ester
• 英文别名: Diethyl 2-methyl-2-[2-(2-trimethylsilylethoxy)prop-2-enyl]propanedioate
• CAS: 207673-91-4
• 化学式: C₁₆H₃₀O₅Si
• 分子量: 330.497
• InChiKey: KIGKNPWIAWICET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Methyl-2-[2-(2-trimethylsilanyl-ethoxy)-allyl]-malonic acid diethyl ester 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以93%的产率得到diethyl 2-methyl-2-(2-oxopropyl)malonate
  参考文献：
  名称：

  A Facile, General Approach to the Synthesis of Electrophilic Acetone Equivalents

  摘要：

  The facile, high-yielding, yet general synthesis of electrophilic chloroacetone equivalents 11a-f is described. The enol ethers are assembled in three steps starting with trichloride 29 in overall yields of 57-93%. Nucleophilic displacement of the chloromethyl chlorine with a range of organometallic reagents generates dichlorides 30 in yields of 58-99%, which can be dehydrohalogenated with t-BuOK/THF in yields of 87-99% to produce enol ethers 31. Conversion of the allyl chlorides 31 to the corresponding allyl iodides 11 with 72-99% yield completes the synthetic sequence. The entire sequence can be performed in less than 48 h on a >50 mmol scale.

  DOI：

  10.1021/jo980094j
• 作为产物：
  描述：

  [2-(1-Chloromethyl-vinyloxy)-ethyl]-trimethyl-silane 在 potassium tert-butylate 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 18.33h， 生成 2-Methyl-2-[2-(2-trimethylsilanyl-ethoxy)-allyl]-malonic acid diethyl ester
  参考文献：
  名称：

  A Facile, General Approach to the Synthesis of Electrophilic Acetone Equivalents

  摘要：

  The facile, high-yielding, yet general synthesis of electrophilic chloroacetone equivalents 11a-f is described. The enol ethers are assembled in three steps starting with trichloride 29 in overall yields of 57-93%. Nucleophilic displacement of the chloromethyl chlorine with a range of organometallic reagents generates dichlorides 30 in yields of 58-99%, which can be dehydrohalogenated with t-BuOK/THF in yields of 87-99% to produce enol ethers 31. Conversion of the allyl chlorides 31 to the corresponding allyl iodides 11 with 72-99% yield completes the synthetic sequence. The entire sequence can be performed in less than 48 h on a >50 mmol scale.

  DOI：

  10.1021/jo980094j

文献信息

• A Facile, General Approach to the Synthesis of Electrophilic Acetone Equivalents
  作者：Slawomir Z. Janicki、Jennifer M. Fairgrieve、Peter A. Petillo

  DOI：10.1021/jo980094j

  日期：1998.5.1

  The facile, high-yielding, yet general synthesis of electrophilic chloroacetone equivalents 11a-f is described. The enol ethers are assembled in three steps starting with trichloride 29 in overall yields of 57-93%. Nucleophilic displacement of the chloromethyl chlorine with a range of organometallic reagents generates dichlorides 30 in yields of 58-99%, which can be dehydrohalogenated with t-BuOK/THF in yields of 87-99% to produce enol ethers 31. Conversion of the allyl chlorides 31 to the corresponding allyl iodides 11 with 72-99% yield completes the synthetic sequence. The entire sequence can be performed in less than 48 h on a >50 mmol scale.