1-triethylsilyloxy-3-(1,3-dithian-2-yl)propane | 404936-40-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: 1-triethylsilyloxy-3-(1,3-dithian-2-yl)propane
• 英文别名: 3-(1,3-Dithian-2-yl)propoxy-triethylsilane
• CAS: 404936-40-9
• 化学式: C₁₃H₂₈OS₂Si
• 分子量: 292.582
• InChiKey: XVCZVRBEDIXXDU-UHFFFAOYSA-N

物化性质

• 沸点：
  345.2±22.0 °C(Predicted)
• 密度：
  0.973±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-triethylsilyloxy-3-(1,3-dithian-2-yl)propane 在 水 、 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 0.58h， 以72%的产率得到2-(3-hydroxypropyl)-1,3-dithiane
  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
• 作为产物：
  描述：

  2-(3-hydroxypropyl)-1,3-dithiane 在 咪唑 、 水 、 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.58h， 生成 1-triethylsilyloxy-3-(1,3-dithian-2-yl)propane
  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

• Synthesis of the Core Structure of Apicularen A by Transannular Cyclization
  作者：Sven M. Kühnert、Martin E. Maier

  DOI：10.1021/ol017261d

  日期：2002.2.1

  [GRAPHICS]An approach to the macrocyclic core of apicularen A is described. Thus, cross-coupling of the aryl triflate 7 with the vinylstannane 19 provided the styrene 20. Deprotection led to the dihydroxy acid 22. Through a size-selective macrolactonization, the 12-membered macrolactone 23 was obtained. Treatment of 24 with N-phenyl selenophthalimide gave the desired trans-pyran 24. This approach might parallel the biosynthetic pathway.
• Facile Cleavage of Triethylsilyl (TES) Ethers Using <i>o</i>-Iodoxybenzoic Acid (IBX) without Affecting <i>tert</i>-Butyldimethylsilyl (TBS) Ethers
  作者：Yikang Wu、Jia-Hui Huang、Xin Shen、Qi Hu、Chao-Jun Tang、Liang Li

  DOI：10.1021/ol025946n

  日期：2002.6.1

  [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.