6-(tert-butyl-dimethyl-silyl)-4-hydroxy-2-trimethylsilylmethyl-hex-1-en-5-ynyl diisopropylcarbamate | 488808-49-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-(tert-butyl-dimethyl-silyl)-4-hydroxy-2-trimethylsilylmethyl-hex-1-en-5-ynyl diisopropylcarbamate
• 英文别名: [(E)-6-[tert-butyl(dimethyl)silyl]-4-hydroxy-2-(trimethylsilylmethyl)hex-1-en-5-ynyl] N,N-di(propan-2-yl)carbamate
• CAS: 488808-49-7
• 化学式: C₂₃H₄₅NO₃Si₂
• 分子量: 439.786
• InChiKey: SIRBNXIKJGPLGZ-CAPFRKAQSA-N

物化性质

• 沸点：
  484.0±45.0 °C(Predicted)
• 密度：
  0.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  反式肉桂醛 、 6-(tert-butyl-dimethyl-silyl)-4-hydroxy-2-trimethylsilylmethyl-hex-1-en-5-ynyl diisopropylcarbamate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以63%的产率得到6-[(tert-butyldimethylsilyl)-ethynyl]-4-methylene-2-styryl-tetrahydropyran-3-yl-diisopropylcarbamate
  参考文献：
  名称：

  Connective Synthesis of Polysubstituted Tetrahydropyrans by a Novel and Stereocontrolled Metallo-ene/Intramolecular Sakurai Cyclization Sequence

  摘要：

  A novel methodology based upon the allylmetalation step followed by an Intramolecular Sakurai Cyclization (IMSC) provides an efficient access to a variety of tetrahydropyran derivatives. This new strategy nicely complements our initial protocol that embodied a tandem ene reaction/IMSC sequence. Both mono- and dihydroxy-tetrahydropyrans could be easily assembled with complete stereocontrol at the various chiral centers.

  DOI：

  10.1021/jo025899c
• 作为产物：
  描述：

  2-[(三甲基硅烷基)甲基]-2-丙烯-1-醇 在 四甲基乙二胺 、 仲丁基锂 、 sodium hydride 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 19.5h， 生成 6-(tert-butyl-dimethyl-silyl)-4-hydroxy-2-trimethylsilylmethyl-hex-1-en-5-ynyl diisopropylcarbamate
  参考文献：
  名称：

  Connective Synthesis of Polysubstituted Tetrahydropyrans by a Novel and Stereocontrolled Metallo-ene/Intramolecular Sakurai Cyclization Sequence

  摘要：

  A novel methodology based upon the allylmetalation step followed by an Intramolecular Sakurai Cyclization (IMSC) provides an efficient access to a variety of tetrahydropyran derivatives. This new strategy nicely complements our initial protocol that embodied a tandem ene reaction/IMSC sequence. Both mono- and dihydroxy-tetrahydropyrans could be easily assembled with complete stereocontrol at the various chiral centers.

  DOI：

  10.1021/jo025899c

文献信息

• Connective Synthesis of Polysubstituted Tetrahydropyrans by a Novel and Stereocontrolled Metallo-ene/Intramolecular Sakurai Cyclization Sequence
  作者：Bernard Leroy、István E. Markó

  DOI：10.1021/jo025899c

  日期：2002.12.1

  A novel methodology based upon the allylmetalation step followed by an Intramolecular Sakurai Cyclization (IMSC) provides an efficient access to a variety of tetrahydropyran derivatives. This new strategy nicely complements our initial protocol that embodied a tandem ene reaction/IMSC sequence. Both mono- and dihydroxy-tetrahydropyrans could be easily assembled with complete stereocontrol at the various chiral centers.