(1R,4R,5S)-4,5-bis(tert-butyl-dimethylsilanyloxy)cyclopent-2-en-1-ol | 501415-75-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,4R,5S)-4,5-bis(tert-butyl-dimethylsilanyloxy)cyclopent-2-en-1-ol
• 英文别名: (1R,4R,5S)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]cyclopent-2-en-1-ol
• CAS: 501415-75-4
• 化学式: C₁₇H₃₆O₃Si₂
• 分子量: 344.642
• InChiKey: UJGZYWSYNQTGTM-KFWWJZLASA-N

物化性质

• 沸点：
  347.7±42.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-甲氧基-1,2-丙二烯 、 (1R,4R,5S)-4,5-bis(tert-butyl-dimethylsilanyloxy)cyclopent-2-en-1-ol 在 palladium diacetate 、 1,3-双(二苯基膦)丙烷 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以97%的产率得到(3R,4S,5R)-3,4-bis-(tert-butyl-dimethylsilanyloxy)-5-(1-methoxyallyloxy)cyclopent-1-ene
  参考文献：
  名称：

  Ruthenium catalyzed ring rearrangement: a rapid entry to substituted aza- and oxacycles

  摘要：

  A ring-closing metathesis (RCM) and a ring-opening metathesis (ROM) are combined in a domino process giving access to a variety of aza- and oxacyles, equipped with highly functionalized side chains, starting from readily accessible cyclopentenyl or cycloheptenyl ethers and amines. The role of different protective groups is examined as well as the influence of the relative configuration of stereocenters of the substrate molecules. Substituted 2,5-dihydro-furans and -pyrroles, 1,2,5,6-tetrahydropyranes and -pyridines as well as 2,3,4,7-tetrahydrooxepines are available via this methodology. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00832-3
• 作为产物：
  描述：

  (1R,3S,4R)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol 在 咪唑 、 sodium hydride 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.66h， 生成 (1R,4R,5S)-4,5-bis(tert-butyl-dimethylsilanyloxy)cyclopent-2-en-1-ol
  参考文献：
  名称：

  Ruthenium catalyzed ring rearrangement: a rapid entry to substituted aza- and oxacycles

  摘要：

  A ring-closing metathesis (RCM) and a ring-opening metathesis (ROM) are combined in a domino process giving access to a variety of aza- and oxacyles, equipped with highly functionalized side chains, starting from readily accessible cyclopentenyl or cycloheptenyl ethers and amines. The role of different protective groups is examined as well as the influence of the relative configuration of stereocenters of the substrate molecules. Substituted 2,5-dihydro-furans and -pyrroles, 1,2,5,6-tetrahydropyranes and -pyridines as well as 2,3,4,7-tetrahydrooxepines are available via this methodology. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00832-3