1-(benzyloxy)-4-[(tert-butyldimethylsilyl)oxy]-2-butyne | 444816-18-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(benzyloxy)-4-[(tert-butyldimethylsilyl)oxy]-2-butyne
• 英文别名: Tert-butyl-dimethyl-(4-phenylmethoxybut-2-ynoxy)silane
• CAS: 444816-18-6
• 化学式: C₁₇H₂₆O₂Si
• 分子量: 290.478
• InChiKey: DRRWLZSAIIPHRM-UHFFFAOYSA-N

物化性质

• 沸点：
  347.8±27.0 °C(Predicted)
• 密度：
  0.959±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  1-(benzyloxy)-4-[(tert-butyldimethylsilyl)oxy]-2-butyne 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 26.5h， 生成 4-benzyloxy-2,3-butynal
  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：

  4-benzyloxy-2-butyn-1-ol 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 49.25h， 生成 1-(benzyloxy)-4-[(tert-butyldimethylsilyl)oxy]-2-butyne
  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

• Ready Access to the Echinopines Skeleton via Gold(I)-Catalyzed Alkoxycyclizations of Enynes
  作者：Ruth Dorel、Antonio M. Echavarren

  DOI：10.1021/acs.joc.6b01607

  日期：2016.9.16

  The [3,5,5,7] tetracyclic skeleton of echinopines has been stereoselectively accessed through a gold(I)-catalyzed alkoxycyclization of cyclopropyl-tethered 1,6-enynes. The key bicyclo[4.2.1]nonane core of the enyne precursors was readily assembled by means of a Co-catalyzed [6 + 2] cycloaddition. Furthermore, the attempted alkoxycyclization of 1,5-enyne substrates revealed an uncovered cyclopropyl

  通过金（I）催化的环丙基束缚的1,6-炔烃的烷氧基环化反应，立体选择性地访问了棘皮碱的[3,5,5,7]四环骨架。烯炔前体的关键双环[4.2.1]壬烷核很容易借助共催化的[6 + 2]环加成反应组装。此外，对1，5-烯炔底物的烷氧基化尝试揭示了未发现的环丙基重排，该环丙基重排产生了[3,6,5,7]四环结构。
• 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.