1-benzyloxy-5-(tert-butyldimethylsilyloxy)-2-pentyne | 713141-44-7

• 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-5-(tert-butyldimethylsilyloxy)-2-pentyne
• 英文别名: Tert-butyl-dimethyl-(5-phenylmethoxypent-3-ynoxy)silane
• CAS: 713141-44-7
• 化学式: C₁₈H₂₈O₂Si
• 分子量: 304.505
• InChiKey: NZLMAPIQYNUOKG-UHFFFAOYSA-N

物化性质

• 沸点：
  365.8±27.0 °C(Predicted)
• 密度：
  0.954±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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-5-(tert-butyldimethylsilyloxy)-2-pentyne 在 Lindlar's catalyst 氨 、 氢气 、 sodium 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (Z)-5-(tert-butyldimethylsilyloxy)pent-2-en-1-ol
  参考文献：
  名称：

  Palladium(II)-catalyzed Stereocontrolled Cyclization via Hemiacetal Intermediates: Total Synthesis of 5-Epi-prelactone C

  摘要：

  Palladium(II)-catalyzed cyclization of 3,7-dihydroxy-4-methyl-5-octenal derivative was carried out to give 2,3,4,6-tetrasubstituted tetrahydropyran with stereoselective 1,3-chirality transfer in net retention of stereochemistry. The cyclized product was converted into 5-epi-prelactone C.

  DOI：

  10.3987/com-04-10034
• 作为产物：
  描述：

  苄基丙炔基醚 在 咪唑 、 正丁基锂 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-benzyloxy-5-(tert-butyldimethylsilyloxy)-2-pentyne
  参考文献：
  名称：

  Palladium(II)-catalyzed Stereocontrolled Cyclization via Hemiacetal Intermediates: Total Synthesis of 5-Epi-prelactone C

  摘要：

  Palladium(II)-catalyzed cyclization of 3,7-dihydroxy-4-methyl-5-octenal derivative was carried out to give 2,3,4,6-tetrasubstituted tetrahydropyran with stereoselective 1,3-chirality transfer in net retention of stereochemistry. The cyclized product was converted into 5-epi-prelactone C.

  DOI：

  10.3987/com-04-10034

文献信息

• A Synthesis of Echinopine B
  作者：Theo D. Michels、Matthew S. Dowling、Christopher D. Vanderwal

  DOI：10.1002/anie.201203147

  日期：2012.7.23

  In a short synthesis of echinopine B, a guaiane‐like intermediate was generated through a methylenecyclopentane annulation onto a substituted cycloheptenone. The resulting bicyclic compound was converted into the natural product by a PtCl2‐catalyzed enyne cycloisomerization (see scheme). Several late‐stage polycyclic rearrangement products were isolated and characterized.

  在棘手类松果碱B的短合成中，通过亚甲基环戊烷环合到取代的环庚烯酮上生成了愈创树状中间体。所得的双环化合物通过PtCl 2催化的烯炔环异构化转化为天然产物（参见方案）。分离并鉴定了几种晚期多环重排产物。
• Palladium(II)-catalyzed Stereocontrolled Cyclization via Hemiacetal Intermediates: Total Synthesis of 5-Epi-prelactone C
  作者：Masahiro Miyazawa、Magsarjav Narantsetseg、Hajime Yokoyama、Seiji Yamaguchi、Yoshiro Hirai

  DOI：10.3987/com-04-10034

  日期：——

  Palladium(II)-catalyzed cyclization of 3,7-dihydroxy-4-methyl-5-octenal derivative was carried out to give 2,3,4,6-tetrasubstituted tetrahydropyran with stereoselective 1,3-chirality transfer in net retention of stereochemistry. The cyclized product was converted into 5-epi-prelactone C.