(S)-(-)-5-p-toluenesulfonylpentane-2-ol | 131701-87-6

• 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)-(-)-5-p-toluenesulfonylpentane-2-ol
• 英文别名: (S)-5-(p-Tolylsulfonyl)-2-pentanol；(2S)-5-(4-methylphenyl)sulfonylpentan-2-ol
• CAS: 131701-87-6
• 化学式: C₁₂H₁₈O₃S
• 分子量: 242.339
• InChiKey: GWOHBYSDRFXGIM-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(-)-5-p-toluenesulfonylpentane-2-ol 在 对甲苯磺酸 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 (6S)-Methyl-2-propyl-3-(p-tolylsulfonyl)-5,6-dihydropyran
  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 bakers' yeast 、 蔗糖 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 以44%的产率得到(S)-(-)-5-p-toluenesulfonylpentane-2-ol
  参考文献：
  名称：

  Synthesis of (S)-(+)-parasorbic acid and (S)-(+)-2-tridecanol acetate: Bakers' yeast reductions of γ and δ ketosulfones

  摘要：

  DOI：

  10.1016/s0040-4039(00)97900-0

文献信息

• Chiral γ and δ Hydroxysulfones via lipase catalyzed resolutions - synthesis of (R)(+)-4-hexanolide and (2R,5S)-2-methyl-5-hexanolide using intramolecular acylation
  作者：Hollie K. Jacobs、Britta H. Mueller、Aravamudan S. Gopalan

  DOI：10.1016/s0040-4020(01)81988-8

  日期：1992.1

  Lipas PS-30 (Amano) was found to be an effective catalyst for enantioselective transesterification of a number of racemic γ and δ hydroxysulfones with isopropenyl acetate in ether. The intramolecular acylation of the ethyl carbonate derivatives obtained from the chiral hydroxysulfones 1d and 1b has been used for the preparation of R(+)-4-hexanolide, sex pheromone of the female dermestid beetle Trogoderma

  发现Lipas PS-30（Amano）是在醚中将许多外消旋γ和δ羟基砜与乙酸异丙烯酯对映选择性酯交换的有效催化剂。从手性羟基砜1d和1b获得的碳酸乙酯衍生物的分子内酰化已用于制备R（+）-4-己内酯，雌性硬皮甲虫Trogoderma glabrum和（2 R，5 S）- 2-甲基-5-己内酯，木匠蜂的性信息素。
• Lipase-catalysed resolution of hydroxy sulfones
  作者：Rafael Chinchilla、Carmen Nájera、José Pardo、Miguel Yus

  DOI：10.1016/0957-4166(90)80004-i

  日期：1990.1
• GOPALAN, ARAVAMUDAN S.;JACOBS, HOLLIE K., TETRAHEDRON LETT., 31,(1990) N9, C. 5575-5578
  作者：GOPALAN, ARAVAMUDAN S.、JACOBS, HOLLIE K.

  DOI：——

  日期：——
• 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：——