(2R,3R)-1-(tert-butyldimethylsilyloxy)-3-(dimethyl(phenyl)silyl)pent-4-en-2-ol | 1276612-70-4

• 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: (2R,3R)-1-(tert-butyldimethylsilyloxy)-3-(dimethyl(phenyl)silyl)pent-4-en-2-ol
• 英文别名: (2R,3R)-1-[tert-butyl(dimethyl)silyl]oxy-3-[dimethyl(phenyl)silyl]pent-4-en-2-ol
• CAS: 1276612-70-4
• 化学式: C₁₉H₃₄O₂Si₂
• 分子量: 350.649
• InChiKey: OLUGYZQDHQEMGI-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 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 (2R,3R)-1-(tert-butyldimethylsilyloxy)-3-(dimethyl(phenyl)silyl)pent-4-en-2-ol 、 (2R,3S)-1-(tert-butyldimethylsilyloxy)-3-(dimethyl(phenyl)silyl)pent-4-en-2-ol 、 (2S,3S)-1-(tert-butyldimethylsilyloxy)-3-(dimethyl(phenyl)silyl)pent-4-en-2-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

文献信息

• Enantioselective Syntheses of <i>syn</i>- and <i>anti</i>-β-Hydroxyallylsilanes Via Allene Hydroboration-Aldehyde Allylboration Reactions
  作者：Ming Chen、William R. Roush

  DOI：10.1021/ol200392u

  日期：2011.4.15

  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.