Trimethyl-(6-methyl-1,4-dioxa-spiro[4.5]dec-2-ylmethyl)-silane | 154557-42-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Trimethyl-(6-methyl-1,4-dioxa-spiro[4.5]dec-2-ylmethyl)-silane
• 英文别名: trimethyl-[(6-methyl-1,4-dioxaspiro[4.5]decan-3-yl)methyl]silane
• CAS: 154557-42-3
• 化学式: C₁₃H₂₆O₂Si
• 分子量: 242.434
• InChiKey: JAMUVLQUXOPCLN-UHFFFAOYSA-N

物化性质

• 沸点：
  290.2±15.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Trimethyl-(6-methyl-1,4-dioxa-spiro[4.5]dec-2-ylmethyl)-silane 在 lithium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 2-甲基环己酮
  参考文献：
  名称：

  The protection of ketones and aldehydes as 4-trimethylsilylmethyl-1,3-dioxolanes

  摘要：

  The 1,3-dioxolanation of carbonyl compounds with 2,3-bis(trimethylsilyloxy)-trimethylsilylpropane (BTTP) in the presence of catalytic amounts of trimethylsilyl trifluoromethanesulfonate (TMSOTf) has been investigated. BTTP readily converted unhindered ketones and aldehydes to their corresponding 4-trimethylsilylmethyl-19-dioxolanes, but failed for more hindered substrates. The 4-trimethylsilylmethyl-1,3-dioxolane can be selectively cleaved to regenerate the carbonyl compound in the presence of a 13-dioxolane using either LiBF4 or HF in acetonitrile.

  DOI：

  10.1016/s0040-4039(00)79941-2
• 作为产物：
  描述：

  3-(三甲基硅基)-1,2-丙二醇 在 吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 Trimethyl-(6-methyl-1,4-dioxa-spiro[4.5]dec-2-ylmethyl)-silane
  参考文献：
  名称：

  The protection of ketones and aldehydes as 4-trimethylsilylmethyl-1,3-dioxolanes

  摘要：

  The 1,3-dioxolanation of carbonyl compounds with 2,3-bis(trimethylsilyloxy)-trimethylsilylpropane (BTTP) in the presence of catalytic amounts of trimethylsilyl trifluoromethanesulfonate (TMSOTf) has been investigated. BTTP readily converted unhindered ketones and aldehydes to their corresponding 4-trimethylsilylmethyl-19-dioxolanes, but failed for more hindered substrates. The 4-trimethylsilylmethyl-1,3-dioxolane can be selectively cleaved to regenerate the carbonyl compound in the presence of a 13-dioxolane using either LiBF4 or HF in acetonitrile.

  DOI：

  10.1016/s0040-4039(00)79941-2