2-(trimethylsilylmethyl)prop-2-enyl N-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-N-propan-2-ylcarbamate | 488808-57-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-(trimethylsilylmethyl)prop-2-enyl N-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-N-propan-2-ylcarbamate
• CAS: 488808-57-7
• 化学式: C₂₉H₄₅NO₃Si₂
• 分子量: 511.852
• InChiKey: HYYNJOJNGRHRFT-UHFFFAOYSA-N

物化性质

• 沸点：
  527.3±50.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilylmethyl)prop-2-enyl N-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-N-propan-2-ylcarbamate 在 正丁基锂 、 二甲基硫 、 四甲基乙二胺 、 三氟化硼乙醚 、 四丁基氟化铵 、 臭氧 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2-Hydroxy-ethyl)-isopropyl-carbamic acid (2R,3S,6S)-4-oxo-2,6-dipropyl-tetrahydro-pyran-3-yl ester
  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 、 N-<2-(tert-butyldiphenylsilyloxy)ethyl>-N-isopropylcarbamoyl chloride 在 sodium hydride 作用下， 以 乙醚 为溶剂， 反应 18.25h， 以71%的产率得到2-(trimethylsilylmethyl)prop-2-enyl N-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-N-propan-2-ylcarbamate
  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.