(E)-1-benzenesulfonyl-1-buten-3-ol | 129083-19-8

• 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: (E)-1-benzenesulfonyl-1-buten-3-ol
• 英文别名: (E)-4-phenylsulfonyl-3-buten-2-ol；(E)-4-(benzenesulfonyl)but-3-en-2-ol
• CAS: 129083-19-8
• 化学式: C₁₀H₁₂O₃S
• 分子量: 212.269
• InChiKey: JABFJGMKUVJZPC-BQYQJAHWSA-N

物化性质

• 熔点：
  74-75 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  420.3±37.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (E)-1-benzenesulfonyl-1-buten-3-ol 在 吡啶 、 4-二甲氨基吡啶 、 tris(dibenzylideneacetone)dipalladium (0) 、 4 Angstroems MS 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.5h， 生成 (4R*,5S*)-3-acetyl-2,4-dimethyl-5-<(phenylsulfonyl)methyl>-4,5-dihydrofuran
  参考文献：
  名称：

  One-Step Palladium-Catalyzed Synthesis of Substituted Dihydrofurans from the Carbonate Derivatives of γ-Hydroxy-α,β-unsaturated Sulfones

  摘要：

  The palladium-catalyzed nucleophilic allylic substitution of the carbonate derivatives of gamma-hydroxy-alpha,beta-unsaturated sulfones (2) with soft carbon nucleophiles such as malonates, beta-keto esters, 1,3-diketones, and alpha-sulfonyl ketones took place cleanly and with full regiocontrol (gamma-substitution). Typical optimized conditions are Pd-2(dba)(3) (5 mol %), dppe (20 mol %), molecular sieves, in toluene-THF at 100 degrees C. Unexpectedly, when beta-keto esters, 1,3-diketones, and alpha-sulfonyl ketones were used as nucleophiles a cascade process occurred, via initial gamma-regioselective allylic substitution and further intramolecular conjugate addition of the enol moiety to the alpha,beta-unsaturated sulfone, to give 2,3,4,5-tetrasubstituted dihydrofurans (13-25) in moderate to good yields. Moreover, the cyclization step is highly stereoselective giving predominantly or exclusively the 4,5-dihydrofuran of trans configuration. From readily available enantiopure (S)-2, this one-step procedure of synthesis of substituted dihydrofurans has been applied to the synthesis of enantiomerically pure tetrasubstituted tetrahydrofurans.

  DOI：

  10.1021/jo981391r
• 作为产物：
  描述：

  苯甲砜 在 哌啶 、 正丁基锂 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 (E)-1-benzenesulfonyl-1-buten-3-ol
  参考文献：
  名称：

  Facile synthesis of E-γ-hydroxy-α,β-unsaturated sulfones from aldehydes

  摘要：

  DOI：

  10.1016/s0040-4039(00)97396-9

文献信息

• β-phenylsulfonylenones as α,β-acetylenic ketones equivalents in diels-alder reactions
  作者：Fernando M. Leon、Juan C. Carretero

  DOI：10.1016/s0040-4039(00)92398-0

  日期：1991.9

  (E)-beta-phenylsulfonylenones, readily prepared by oxidation of the alcohols, react with a wide variety of dienes in the presence of activated silica gel. The basic elimination of the phenylsulfonyl group in the resulting adducts gives high yields of the corresponding enones, thus showing the usefulness of these dienophiles as reactive synthetic equivalents of alpha,beta-acetylenic ketones.

  （E）-β-苯甲基砜基烯酮，经由醇的氧化即可制备，与活性硅凝胶共存的多种共轭烯烃发生反应。在加成产物中，苯甲基砜基的基消除反应可获得高产率的相应的烯酮，这表明这些烯烃作为活性合成等效物，对于α,β-烯丙酮类化合物具有重要的作用价值。
• An efficient preparation of optically active (E)-γ-hydroxy-α,β-unsaturated phenyl sulfones using lipase-mediated acylations
  作者：Esteban Domínguez、Juan Carlos Carretero、Alfonso Fernández-Mayoralas、Santiago Conde

  DOI：10.1016/s0040-4039(00)93455-5

  日期：1991.9

  (E)-gamma-Hydroxy-alpha,beta-unsaturated phenyl sulfones have been efficiently resolved via irreversible enzymatic acylation with lipase PS (pseudomonas cepacia) and vinyl acetate. This process has been applied to the synthesis of the aggregation pheromone (-)-(3S,4S)-4-methyl-3-heptanol.

  (E)-γ-羟基α,β-不饱和苯砜在双歧杆菌PS（双歧杆菌Cepacia）酶催作用以及乙酰醋酸二注射液的配合下，通过不可逆的酶促甲基化过程得到脱炔酮双键。此方法已被用于合成的聚合外ustedache，（-）-（3S,4S）—4-甲基-3-Heptanol。
• Iodosulfonation of alkenes with benzenesulfinic acid – <i>N</i>-iodosuccinimide — Facile preparation of α,β-unsaturated sulfones
  作者：Russell R Wolff、Vikram Basava、Robert M Giuliano、Walter J Boyko、J Herman Schauble

  DOI：10.1139/v06-051

  日期：2006.4.1

  Reaction of alkenes and alkenols with N-iodosuccinimide (NIS) and benzenesulfinic acid in dichloromethane at room temperature affords vic-iodophenylsulfonyl adducts in good to high yields. Treatment of the iodosulfones with neutral alumina in dichloromethane at room temperature results in dehydroiodination to give the corresponding vinyl sulfones in high yield and purity by this convenient two-step procedure. Application of the iodosulfonation–dehydroiodination sequence to allylic alcohols and silyl ethers gave γ-oxygenated, α,β-unsaturated phenylsulfones, while the attempted iodosulfonation of glycals, as intermediates to vinyl sulfones, resulted in addition of benzenesulfinic acid with double bond shift (Ferrier rearrangement). Key words: iodosulfonation, vinyl sulfones, benzenesulfinic acid, N-iodosuccinimide, dehydroiodination.

  室温下，烯和烯醇与 N-iodosuccinimide (NIS) 和苯亚磺酸在二氯甲烷中发生反应，生成的邻碘苯磺酰基加合物收率高。在室温下，用中性氧化铝在二氯甲烷中处理碘砜，然后进行脱氢碘化，通过这种简便的两步法得到相应的乙烯基砜，收率和纯度都很高。将碘磺化脱氢碘化顺序应用于烯丙基醇和硅基醚，可得到γ-氧合的、α,β-不饱和的苯基砜，而尝试对作为乙烯基砜中间体的甘油进行碘磺化，则会导致苯亚磺酸的加成和双键转移（费里尔重排）。关键词：碘磺化、乙烯基砜、苯亚磺酸、N-碘代丁二酰亚胺、脱氢碘化。
• Synthesis and conjugate additions to (E)-γ-alkoxy-α-substituted-α,β-unsaturated sulfones
  作者：Carmen Alcaraz、Juan C. Carretero、Esteban Domínguez

  DOI：10.1016/s0040-4039(00)79674-2

  日期：1991.3

  (E)-gamma-hydroxy-alpha,beta-unsaturated sulfones have been readily functionalized at alpha-position via protection of hydroxyl group, metalation with n-BuLi and subsequent reaction with electrophiles. The conjugate addition of organolithiums to (E)-gamma-methoxymethoxy-alpha-trimethylsilyl-alpha, beta-unsaturated phenyl sulfones in Et2O is highly syn-stereoselective.

  (E)-γ-羟基-α,β-未饱和砜经过羟基的保护后，可以在α位置容易地进行功能化反应。添加三甲基--硅基α,β-未饱和苯砜的有机锂试剂在乙醚中的共轭加成具有高度的合成同素异构选择性。
• Stereoselective synthesis of substituted γ-butyrolactones from γ-hydroxy-α,β-unsaturated phenyl sulfones
  作者：Javier Rojo、Mercedes García、Juan C Carretero

  DOI：10.1016/s0040-4020(01)80181-2

  日期：1993.1

  α-(phenylsulfonyl)-α,β-unsaturated esters 3 or α-(phenylsulfonyl)butenolides 4 is described. This method is based on the conjugate addition of organoaluminum reagents (Me3Al, Et3Al and Et2AlCN) to substrates 3 and 4. Whereas the conjugate addition to Michael acceptors 3 occurs with complete syn-selectivity, the conjugate addition to butenolides 4 is usually anti-selective. This methodology has been applied

  描述了从容易获得的α-（苯磺酰基）-α，β-不饱和酯3或α-（苯磺酰基）丁烯化物4开始制备顺式和反式双取代（和三取代）γ-内酯的立体选择路线。该方法基于将有机铝试剂（Me 3 Al，Et 3 Al和Et 2 AlCN）共轭添加到基质3和4上。尽管共轭加成到迈克尔受体3时具有完全的同选择性，而共轭加成成丁烯脂类4通常是反选择的。该方法已经应用于（-）-顺式白兰地内酯的立体选择性和对映选择性合成。