(S)-4-[tert-Butyldimethylsilyloxy]-2-phenylsulfonyl-2-cyclopentenone | 212055-65-7

• 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)-4-[tert-Butyldimethylsilyloxy]-2-phenylsulfonyl-2-cyclopentenone
• 英文别名: (S)-2-benzenesulfonyl-4-(tert-butyldimethylsilyloxy)-2-cyclopentenone；(4S)-2-(benzenesulfonyl)-4-[tert-butyl(dimethyl)silyl]oxycyclopent-2-en-1-one
• CAS: 212055-65-7
• 化学式: C₁₇H₂₄O₄SSi
• 分子量: 352.527
• InChiKey: SHVMGWMLYBFLRT-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-[tert-Butyldimethylsilyloxy]-2-phenylsulfonyl-2-cyclopentenone 在 samarium diiodide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 甲苯 为溶剂， 反应 1.17h， 生成 (3S,4R)-3-(tert-butyldimethylsilyloxy)-4-methylcyclopentanone
  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：

  methyl (S)-3,4-bis(tert-butyldimethylsilyloxy)butanoate 在 dirhodium tetraacetate 、 对甲苯磺酰叠氮 、 lithium aluminium deuteride 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 1.42h， 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

文献信息

• Control of Chemoselectivity in Dirhodium(II)-Catalyzed Reaction of 5,6-Dioxygenated 2-Diazo-3-oxohexanoates: C-H Insertion Reaction versus Oxonium Ylide Formation.
  作者：Takayuki YAKURA、Akiharu UEKI、Yukiko MORIOKA、Toyoshige KURATA、Kenji TANAKA、Masazumi IKEDA

  DOI：10.1248/cpb.46.1182

  日期：——

  Methyl (S)-2-diazo-4-(3, 3-dimethyl-2, 4-dioxolan-1-yl)-3-oxobutanoate (1), upon treatment with Rh2(OAc)4 in boiling dichloromethane, gave methyl (1S, 5S)-2, 2-dimethyl-7-oxo-3, 8-dioxabicyclo[3.2.1]octane-1-carboxylate (2) via oxonium ylide formation/1, 2-shift. On the other hand, similar treatment of methyl (S)-5, 6-bis(tert-butyldimethylsilyloxy)-2-diazo-3-oxohexanoate (3a) gave methyl 3-(tert-butyldimethylsilyloxy)-5-oxo-1-cyclopentene-1-carboxylate (4a) via the C-H insertion reaction.

  (S)-2-重氮-4-(3, 3-二甲基-2, 4-二氧戊环-1-基)-3-氧代丁酸甲酯(1)在沸腾的二氯甲烷中用 Rh2(OAc)4 处理后，通过羰基锍形成/1, 2-移位，得到(1S, 5S)-2, 2-二甲基-7-氧代-3, 8-二氧杂环[3.2.1]辛烷-1-甲酸甲酯(2)。另一方面，通过 C-H 插入反应，对 (S)-5，6-双（叔丁基二甲基硅氧基）-2-重氮-3-氧代己酸甲酯（3a）进行类似处理，可得到 3-（叔丁基二甲基硅氧基）-5-氧代-1-环戊烯-1-甲酸甲酯（4a）。
• Stereoselective Conjugate Addition of Alkyl Groups to (<i>S</i>)-4-(<i>tert</i>-Butyldimethylsilyloxy)-2-phenylsulfonyl-2-cyclopentenone by Means of Trialkylaluminum Reagents
  作者：Takayuki Yakura、Kenji Tanaka、Miki Iwamoto、Masatake Nameki、Masazumi Ikeda

  DOI：10.1055/s-1999-2823

  日期：1999.8
• 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.