1-(triethylsilyloxy)-4-(2',2'-dimethyl-1',3'dioxolan-4'-yl)-butane | 444816-14-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(triethylsilyloxy)-4-(2',2'-dimethyl-1',3'dioxolan-4'-yl)-butane
• 英文别名: 4-(2,2-Dimethyl-1,3-dioxolan-4-yl)butoxy-triethylsilane
• CAS: 444816-14-2
• 化学式: C₁₅H₃₂O₃Si
• 分子量: 288.503
• InChiKey: MALNFUKYYSPQOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  309.7±17.0 °C(Predicted)
• 密度：
  0.898±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(triethylsilyloxy)-4-(2',2'-dimethyl-1',3'dioxolan-4'-yl)-butane 在 iron(III) sulfate 作用下， 以 甲醇 为溶剂， 反应 0.6h， 以95%的产率得到4-(2,2-dimethyl-1,3-dioxolane-4-yl)-1-butanol
  参考文献：
  名称：

  Facile Cleavage of Silyl Protecting Groups with Catalytic Amounts of FeCl₃

  摘要：

  本文介绍了一种温和且环境友好的方法，使用催化量的铁离子在甲醇中去除硅烷保护基团。该方法特别有效地裂解了三乙基硅烷（TES）保护基团。

  DOI：

  10.1055/s-2006-926256
• 作为产物：
  描述：

  4-(2,2-dimethyl-1,3-dioxolane-4-yl)-1-butanol 、 三乙基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以98%的产率得到1-(triethylsilyloxy)-4-(2',2'-dimethyl-1',3'dioxolan-4'-yl)-butane
  参考文献：
  名称：

  Facile Cleavage of Triethylsilyl (TES) Ethers Using o-Iodoxybenzoic Acid (IBX) without Affecting tert-Butyldimethylsilyl (TBS) Ethers

  摘要：

  [GRAPHICS]In DMSO cleavage of triethylsilyl (TES) ethers by o-iodoxybenzoic acid (IBX) was significantly faster than cleavage of tart-butyldimethylsilyl (TBS) ethers or further oxidation into carbonyl compounds. In most cases, TES protecting groups could be removed in good to excellent yields within 1 h, whereas similar TBS protecting groups remained intact under the same conditions. The procedure also could be adapted for direct one-pot conversion of TES ethers into carbonyl compounds.

  DOI：

  10.1021/ol025946n

文献信息

• Efficient chemoselective deprotection of silyl ethers using catalytic 1-chloroethyl chloroformate in methanol
  作者：Chang-Eun Yeom、Young Jong Kim、So Young Lee、Yong Je Shin、B. Moon Kim

  DOI：10.1016/j.tet.2005.10.043

  日期：2005.12

  Fast and chemoselective desilylation of silyl-protected alcohols was achieved using a catalytic amount of 1-chloroethyl chloroformate in methanol. With a minimal amount of 1-chloroethyl chloroformate as the source for anhydrous HCl, extremely efficient cleavage of silyl ethers of primary and secondary alcohols was accomplished, and chemoselective deprotection of one silyl ether in the presence of another silyl or other acid-labile group was possible through controlling the amount of the chloroformate and reaction time. (c) 2005 Elsevier Ltd. All rights reserved.