(S)-1-Methyl-3-(p-tolylsulfonyl)propyl-N,N-dimethylcarbamate | 155729-14-9

• 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-Methyl-3-(p-tolylsulfonyl)propyl-N,N-dimethylcarbamate
• 英文别名: [(2S)-4-(4-methylphenyl)sulfonylbutan-2-yl] N,N-dimethylcarbamate
• CAS: 155729-14-9
• 化学式: C₁₄H₂₁NO₄S
• 分子量: 299.391
• InChiKey: MXJFMEPPOZARFW-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-1-Methyl-3-(p-tolylsulfonyl)propyl-N,N-dimethylcarbamate 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以60.3%的产率得到(4S)-4-hydroxy-N,N-dimethyl-2-(4-methylphenyl)sulfonylpentanamide
  参考文献：
  名称：

  Facile Intramolecular Acylation Reactions of .gamma.- and .delta.-(Acyloxy)Sulfones: Synthesis of Substituted Chiral Dihydrofurans and Dihydropyrans

  摘要：

  The acylation ai (S)-4-(p-tolylsulfonly)-2-butanol and (S)-(p-tolylsulfonyl)-3-pentanal, chirons that are available in high optical purities, with a variety of acid chlorides gave the corresponding derivatives 9-16. Deprotonation of these substrates with LHMDS in THF at -78 degrees C led to the selective formation of the or-sulfonyl carbanions. These carbanions cyclized readily to give in good yields an equilibrium mixture of the expected lactols with the open chain hydroxy ketones. This ring closure/acyl transfer reaction was facile and found to be compatible with functionalities such as halides and esters in the acyl side chain. The mixture of lactols with the open chain hydroxy ketones obtained from this reaction could be dehydrated in good yields using mild acid conditions to give the corresponding chiral nonracemic dihydrofurans or dihydropyrans. Alternatively, this equilibrium mixture could be trapped as the open-chain (tert-butyldimethylsilyl) oxy ketosulfone derivatives 32-35 and subsequently desulfonylated.

  DOI：

  10.1021/jo00087a014
• 作为产物：
  描述：

  5-(p-Tolylsulfonyl)pentan-2-one 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 72.0h， 生成 (S)-1-Methyl-3-(p-tolylsulfonyl)propyl-N,N-dimethylcarbamate
  参考文献：
  名称：

  Facile Intramolecular Acylation Reactions of .gamma.- and .delta.-(Acyloxy)Sulfones: Synthesis of Substituted Chiral Dihydrofurans and Dihydropyrans

  摘要：

  The acylation ai (S)-4-(p-tolylsulfonly)-2-butanol and (S)-(p-tolylsulfonyl)-3-pentanal, chirons that are available in high optical purities, with a variety of acid chlorides gave the corresponding derivatives 9-16. Deprotonation of these substrates with LHMDS in THF at -78 degrees C led to the selective formation of the or-sulfonyl carbanions. These carbanions cyclized readily to give in good yields an equilibrium mixture of the expected lactols with the open chain hydroxy ketones. This ring closure/acyl transfer reaction was facile and found to be compatible with functionalities such as halides and esters in the acyl side chain. The mixture of lactols with the open chain hydroxy ketones obtained from this reaction could be dehydrated in good yields using mild acid conditions to give the corresponding chiral nonracemic dihydrofurans or dihydropyrans. Alternatively, this equilibrium mixture could be trapped as the open-chain (tert-butyldimethylsilyl) oxy ketosulfone derivatives 32-35 and subsequently desulfonylated.

  DOI：

  10.1021/jo00087a014

文献信息

• Jacobs Hollie K., Gopalan Aravamudan S., J. Org. Chem, 59 (1994) N 8, S 2014-2019
  作者：Jacobs Hollie K., Gopalan Aravamudan S.

  DOI：——

  日期：——
• Facile Intramolecular Acylation Reactions of .gamma.- and .delta.-(Acyloxy)Sulfones: Synthesis of Substituted Chiral Dihydrofurans and Dihydropyrans
  作者：Hollie K. Jacobs、Aravamudan S. Gopalan

  DOI：10.1021/jo00087a014

  日期：1994.4

  The acylation ai (S)-4-(p-tolylsulfonly)-2-butanol and (S)-(p-tolylsulfonyl)-3-pentanal, chirons that are available in high optical purities, with a variety of acid chlorides gave the corresponding derivatives 9-16. Deprotonation of these substrates with LHMDS in THF at -78 degrees C led to the selective formation of the or-sulfonyl carbanions. These carbanions cyclized readily to give in good yields an equilibrium mixture of the expected lactols with the open chain hydroxy ketones. This ring closure/acyl transfer reaction was facile and found to be compatible with functionalities such as halides and esters in the acyl side chain. The mixture of lactols with the open chain hydroxy ketones obtained from this reaction could be dehydrated in good yields using mild acid conditions to give the corresponding chiral nonracemic dihydrofurans or dihydropyrans. Alternatively, this equilibrium mixture could be trapped as the open-chain (tert-butyldimethylsilyl) oxy ketosulfone derivatives 32-35 and subsequently desulfonylated.