(S)-1-benzenesulfonyl-4,5-bis(tert-butyldimethylsilyloxy)-2-pentanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-1-benzenesulfonyl-4,5-bis(tert-butyldimethylsilyloxy)-2-pentanone
• 英文别名: (4S)-1-(benzenesulfonyl)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]pentan-2-one
• 化学式: C₂₃H₄₂O₅SSi₂
• 分子量: 486.82
• InChiKey: BLZPRRLBSSSUFC-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-1-benzenesulfonyl-4,5-bis(tert-butyldimethylsilyloxy)-2-pentanone 在 dirhodium tetraacetate 、 对甲苯磺酰叠氮 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.25h， 生成 (S)-4-[tert-Butyldimethylsilyloxy]-2-phenylsulfonyl-2-cyclopentenone
  参考文献：
  名称：

  Stereoselective Conjugate Addition of Alkyl Groups to ( S )-4-( tert -Butyldimethylsilyloxy)-2-cyclopentenone Derivatives

  摘要：

  Reaction of (S)-2-benzenesulfonyl-4-(tert-butyldimethylsilyloxy)-2-cyclopentenone (2) and a 2-methoxycarbonyl congener (3) with R2CuLi or RMgBr-CuI stereoselectively gave (2S,3R,4S)-3-alkyl-2-benzenesulfonyl-4-(tert-butyldimethylsilyloxy)cyclopentanone (4) and its (2S,3S,4S)-2-methoxycarbonyl derivative (5) as a major diastereoisomer. On the other hand, reaction with R3Al in toluene exclusively gave the corresponding 3,4-cis-adducts 6 and 7. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00686-4
• 作为产物：
  描述：

  苯甲砜 、 methyl (S)-3,4-bis(tert-butyldimethylsilyloxy)butanoate 在 lithium aluminium deuteride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.17h， 以75%的产率得到(S)-1-benzenesulfonyl-4,5-bis(tert-butyldimethylsilyloxy)-2-pentanone
  参考文献：
  名称：

  Stereoselective Conjugate Addition of Alkyl Groups to ( S )-4-( tert -Butyldimethylsilyloxy)-2-cyclopentenone Derivatives

  摘要：

  Reaction of (S)-2-benzenesulfonyl-4-(tert-butyldimethylsilyloxy)-2-cyclopentenone (2) and a 2-methoxycarbonyl congener (3) with R2CuLi or RMgBr-CuI stereoselectively gave (2S,3R,4S)-3-alkyl-2-benzenesulfonyl-4-(tert-butyldimethylsilyloxy)cyclopentanone (4) and its (2S,3S,4S)-2-methoxycarbonyl derivative (5) as a major diastereoisomer. On the other hand, reaction with R3Al in toluene exclusively gave the corresponding 3,4-cis-adducts 6 and 7. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00686-4

文献信息

• Stereoselective Conjugate Addition of Alkyl Groups to ( S )-4-( tert -Butyldimethylsilyloxy)-2-cyclopentenone Derivatives
  作者：Takayuki Yakura、Kenji Tanaka、Tomoko Kitano、Jun'ichi Uenishi、Masazumi Ikeda

  DOI：10.1016/s0040-4020(00)00686-4

  日期：2000.9

  Reaction of (S)-2-benzenesulfonyl-4-(tert-butyldimethylsilyloxy)-2-cyclopentenone (2) and a 2-methoxycarbonyl congener (3) with R2CuLi or RMgBr-CuI stereoselectively gave (2S,3R,4S)-3-alkyl-2-benzenesulfonyl-4-(tert-butyldimethylsilyloxy)cyclopentanone (4) and its (2S,3S,4S)-2-methoxycarbonyl derivative (5) as a major diastereoisomer. On the other hand, reaction with R3Al in toluene exclusively gave the corresponding 3,4-cis-adducts 6 and 7. (C) 2000 Elsevier Science Ltd. All rights reserved.