[2-(1-Iodomethyl-vinyloxymethoxy)-ethyl]-trimethyl-silane | 207673-81-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2-(1-Iodomethyl-vinyloxymethoxy)-ethyl]-trimethyl-silane
• 英文别名: 2-(3-Iodoprop-1-en-2-yloxymethoxy)ethyl-trimethylsilane
• CAS: 207673-81-2
• 化学式: C₉H₁₉IO₂Si
• 分子量: 314.239
• InChiKey: JSAXRMUGJYLWTM-UHFFFAOYSA-N

物化性质

• 沸点：
  269.6±35.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲基丙二酸二乙酯 、 [2-(1-Iodomethyl-vinyloxymethoxy)-ethyl]-trimethyl-silane 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到2-Methyl-2-[2-(2-trimethylsilanyl-ethoxymethoxy)-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
• 作为产物：
  描述：

  2-(1,3-Dichloropropan-2-yloxymethoxy)ethyl-trimethylsilane 在 potassium tert-butylate 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 12.0h， 生成 [2-(1-Iodomethyl-vinyloxymethoxy)-ethyl]-trimethyl-silane
  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