(3-hydroxy)butyl p-tolyl sulfone | 105363-56-2

• 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: (3-hydroxy)butyl p-tolyl sulfone
• 英文别名: 4-(4-Methylbenzene-1-sulfonyl)butan-2-ol；4-(4-methylphenyl)sulfonylbutan-2-ol
• CAS: 105363-56-2
• 化学式: C₁₁H₁₆O₃S
• 分子量: 228.312
• InChiKey: HXWQINCGFDFKHE-UHFFFAOYSA-N

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：

  (3-hydroxy)butyl p-tolyl sulfone 在 二苯基二硒醚 、 双氧水 、 silver(l) oxide 、 lithium diisopropyl amide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 49.5h， 生成 (E)-3-methoxy-1-tosyl-1-butene
  参考文献：
  名称：

  Stereochemistry of the Conversion of γ-Substituted (E)-Vinylsulfones to the Corresponding Allylsulfones. Determination of the Relative Degree of “Syn-Effect”

  摘要：

  通过观察所得烯丙基砜的 E/Z 比值，确定了 γ-取代的乙烯基砜在与 1,8-二氮杂双环[5.4.0]十一-7-烯（DBU）一起转化为相应的烯丙基砜时的 "协同效应 "相对程度如下：CH3O- ≥ AcO- > CH3- > -CH2- >> t-Bu- 和 Ph-。

  DOI：

  10.1246/cl.1988.2009
• 作为产物：
  描述：

  4-(甲苯-4-磺酰基)-2-丁酮 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 (3-hydroxy)butyl p-tolyl sulfone
  参考文献：
  名称：

  “Syn-Effect” in the Conversion of (E)-Vinylic Sulfones to the Corresponding Allylic Sulfones

  摘要：

  研究发现，在温和条件下通过碱性处理，(E)-乙烯基砜类化合物倾向于优先形成动力学控制的(Z)-烯丙基砜类产物，而(Z)-乙烯基砜则生成(E)-烯丙基砜。这种立体化学关系可通过“邻位效应”来解释，并且通过观察相应的γ-单取代或γ,γ-双取代乙烯基砜所生成的烯丙基砜的E/Z比率，确定了不同取代基的相对程度如下：RO–（R=CH3, C2H5）＞ ArO–（Ar=p-CH3OC6H4, p-CH3C6H4, C6H5, p-NO2C6H4）≥ AcO–＞ Cl– ≥ Br–＞ CH3–＞ CH3S– ≥ –CH2–（环状和非环状）＞(CH3)2CH–>＞(CH3)3C–, C6H5–。对一些乙烯基砜进行了X射线晶体学分析，以揭示“邻位效应”的起源。

  DOI：

  10.1246/bcsj.65.75
• 作为试剂：
  描述：

  3-苯丙酸乙酯 在 正丁基锂 、 (3-hydroxy)butyl p-tolyl sulfone 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到dl-Aethyl 2-benzyl-3-oxo-5-phenylpentanoat
  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

• 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。
• Stereochemistry of the Conversion of γ-Substituted (<i>E</i>)-Vinylsulfones to the Corresponding Allylsulfones. Determination of the Relative Degree of “Syn-Effect”
  作者：Katsuhiko Inomata、Takaki Hirata、Hiroshi Suhara、Hideki Kinoshita、Hiroshi Kotake、Hitoshi Senda

  DOI：10.1246/cl.1988.2009

  日期：1988.12.5

  The relative degree of “syn-effect” for the γ-substituted vinylsulfones in their conversion to the corresponding allylsulfones with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was determined by observing E/Z ratios of the resulting allylsulfones as follows: CH3O– ≥ AcO– > CH3– > –CH2– >> t-Bu– and Ph–.

  通过观察所得烯丙基砜的 E/Z 比值，确定了 γ-取代的乙烯基砜在与 1,8-二氮杂双环[5.4.0]十一-7-烯（DBU）一起转化为相应的烯丙基砜时的 "协同效应 "相对程度如下：CH3O- ≥ AcO- > CH3- > -CH2- >> t-Bu- 和 Ph-。
• Haloisoquinoline carboxamide
  申请人：Emory University

  公开号：US05998624A1

  公开（公告）日：1999-12-07

  Compounds of the invention have the general structure ##STR1## X, Y or Z are, respectively independently, H, F or an isotope thereof, Br or an isotope thereof, I or an isotope thereof, At or an isotope thereof, (R.sub.1)W or (R.sub.2)V and R is --(R.sub.1)W, when W is H or F or an isotope thereof, R.sub.1 is linear or branched alkyl of 1-4 carbon atoms, R.sub.2 is vinyl, V is I or an isotope thereof and at least one of X, Y or Z is not H. The compounds of the invention bind to PK receptors.

  本发明的化合物具有以下通式：##STR1## 其中，X、Y或Z分别独立地为H、F或其同位素、Br或其同位素、I或其同位素、At或其同位素、(R.sub.1)W或(R.sub.2)V，且R为--(R.sub.1)W，当W为H、F或其同位素时，R.sub.1为1-4个碳原子的线性或支链烷基，R.sub.2为乙烯基，V为I或其同位素，并且X、Y或Z中至少有一个不为H。本发明的化合物与PK受体结合。
• Nwaukwa, Stephen O.; Lee, Susanna; Keehn, Philip M., Synthetic Communications, 1986, vol. 16, # 3, p. 309 - 330
  作者：Nwaukwa, Stephen O.、Lee, Susanna、Keehn, Philip M.

  DOI：——

  日期：——
• Remote participation during photooxidation at sulfur. Evidence for sulfurane intermediates
  作者：E. L. Clennan、Kang Yang

  DOI：10.1021/jo00042a031

  日期：1992.7

  The photooxidations of geminally substituted gamma-hydroxy sulfides results in formation of unusual oxidative elimination products. Detailed spectral data and the independent synthesis of a close analogue provide compelling evidence for the structures of these olefins. The formation of the olefins is attributed to decomposition of sulfurane intermediates. This conclusion is supported by a detailed kinetic study which separated the chemical, k(r), and physical, k(q), components to the overall deactivation of singlet oxygen. Those sulfides with the best geometry for sulfide-hydroxyl interaction are also the substrates which react most rapidly with singlet oxygen to give oxidation products. In addition, sulfone yields are in excess of 50% for the hydroxy-substituted sulfides but less than 5% for their hydrocarbon analogues. Several mechanisms that provide explanations for these unusually high sulfone yields are presented.