(3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-cyclohexanone | 276879-12-0

• 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: (3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-cyclohexanone
• 英文别名: (3S,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-methylcyclohexan-1-one
• CAS: 276879-12-0
• 化学式: C₂₀H₄₂O₃Si₂
• 分子量: 386.723
• InChiKey: NUCANRYSMBJOTP-NJAFHUGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.01
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-cyclohexanone 在 四丁基氟化铵 作用下， 生成 (4S,5R)-4-Hydroxymethyl-5-methyl-cyclohex-2-enone
  参考文献：
  名称：

  Optically active trans-4-(tert-butyldimethylsiloxymethyl)-5-(tert-butyldimethylsiloxy)-2-cyclohexenone as a useful chiral building block for preparation of substituted cyclohexane rings: synthesis and its highly stereoselective reaction with RCu(CN)Li

  摘要：

  Optically active trans-4-(tert-butyldimethylsiloxymethyl)-5-(tert-butyldimethylsiloxy)-2cyclohexenone (2) has been synthesized in 25% overall yield starting from easily available 1,4-bis(benzyloxy)-2,3-epoxy butane (3). The enone 2 reacts with excellent stereoselectivity with RCu(CN)Li thus working as an efficient chiral building block for preparation of substituted cyclohexane compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00239-2
• 作为产物：
  描述：

  tert-Butyl-dimethyl-((S)-(S)-2-oxiranyl-but-3-enyloxy)-silane 在 咪唑 、 titanium(IV) isopropylate 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 异丙基氯化镁 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 2.0h， 生成 (3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-cyclohexanone
  参考文献：
  名称：

  Optically active trans-4-(tert-butyldimethylsiloxymethyl)-5-(tert-butyldimethylsiloxy)-2-cyclohexenone as a useful chiral building block for preparation of substituted cyclohexane rings: synthesis and its highly stereoselective reaction with RCu(CN)Li

  摘要：

  Optically active trans-4-(tert-butyldimethylsiloxymethyl)-5-(tert-butyldimethylsiloxy)-2cyclohexenone (2) has been synthesized in 25% overall yield starting from easily available 1,4-bis(benzyloxy)-2,3-epoxy butane (3). The enone 2 reacts with excellent stereoselectivity with RCu(CN)Li thus working as an efficient chiral building block for preparation of substituted cyclohexane compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00239-2