(3R,4R)-1-(tert-butyldimethylsilyloxy)-4-(dimethyl(phenyl)silyl)hex-5-en-3-ol | 1276612-68-0

• 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: (3R,4R)-1-(tert-butyldimethylsilyloxy)-4-(dimethyl(phenyl)silyl)hex-5-en-3-ol
• 英文别名: (3R,4R)-1-[tert-butyl(dimethyl)silyl]oxy-4-[dimethyl(phenyl)silyl]hex-5-en-3-ol
• CAS: 1276612-68-0
• 化学式: C₂₀H₃₆O₂Si₂
• 分子量: 364.676
• InChiKey: BBGKBTGZIWRRPN-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.93
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  allenyldimethyl(phenyl)silane 以 甲苯 为溶剂， 反应 17.0h， 生成 (3R,4R)-1-(tert-butyldimethylsilyloxy)-4-(dimethyl(phenyl)silyl)hex-5-en-3-ol 、 (3R,4S)-1-(tert-butyldimethylsilyloxy)-4-(dimethyl(phenyl)silyl)hex-5-en-3-ol 、 (3S,4S)-1-(tert-butyldimethylsilyloxy)-4-(dimethyl(phenyl)silyl)hex-5-en-3-ol
  参考文献：
  名称：

  Enantioselective Syntheses of syn- and anti-β-Hydroxyallylsilanes Via Allene Hydroboration-Aldehyde Allylboration Reactions

  摘要：

  The kinetic hydroboration of allenylsilane 5 with ((d)Ipc)(2)BH at -40 degrees C provides allylborane 9Z with >= 12:1 selectivity. When the hydroboration is performed at temperatures above -40 degrees C, 9Z isomerizes to the thermodynamically more stable allylborane 9E with >20:1 selectivity. Subsequent treatment of 9Z or 9E with aldehydes at -78 degrees C provides syn- or anti-beta-hydroxyallylsilanes, 7 or 8, respectively.

  DOI：

  10.1021/ol200392u