(2S)-4-(4-methylphenyl)sulfonylbutan-2-ol | 131701-86-5

• 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: (2S)-4-(4-methylphenyl)sulfonylbutan-2-ol
• CAS: 131701-86-5
• 化学式: C₁₁H₁₆O₃S
• 分子量: 228.312
• InChiKey: HXWQINCGFDFKHE-JTQLQIEISA-N

物化性质

• 沸点：
  415.2±45.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  (2S)-4-(4-methylphenyl)sulfonylbutan-2-ol 在 盐酸 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 乙醚 为溶剂， 反应 5.0h， 生成 (S)-2-<2-(Ethoxycarbonyl)ethyl>-5-methyl-3-(p-tolylsulfonyl)-4,5-dihydrofuran
  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：

  (E,2S)-4-(4-methylphenyl)sulfonyl-4-methylsulfanylbut-3-en-2-ol 在 sodium tetrahydroborate 、 Raney Ni (W₂) 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 21.0h， 生成 (2S)-4-(4-methylphenyl)sulfonylbutan-2-ol
  参考文献：
  名称：

  3-羟基-1-（甲硫基）-1-（对甲苯磺酰基）-1-烯烃的高度立体选择性自由基加成及其在制备旋光化合物中的应用

  摘要：

  通过在3-羟基-1-（甲硫基）-1-（对甲苯磺酰基）-1-烯烃及其乙酸酯中添加1-羟基烷基（R 2 C-OH）实现了有效的1,2-不对称诱导（1）：在醇（R 2 CHOH）中照射1和二苯甲酮得到具有高顺式选择性的加合物（2）。光学活性的1是由脂肪酶PS催化的酯交换的方法，因此，本自由基不对称诱导提供了导致各种手性化合物的合成途径可以容易地获得。

  DOI：

  10.1016/s0040-4020(97)00545-0

文献信息

• Synthesis of (S)-(+)-parasorbic acid and (S)-(+)-2-tridecanol acetate: Bakers' yeast reductions of γ and δ ketosulfones
  作者：Aravamudan S. Gopalan、Hollie K. Jacobs

  DOI：10.1016/s0040-4039(00)97900-0

  日期：——
• 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：——
• 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.