(E)-4-hydroxy-2-butenyl phenyl sulfide | 121666-84-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (E)-4-hydroxy-2-butenyl phenyl sulfide
• 英文别名: (E)-4-phenylsulfanyl-but-2-en-1-ol；(E)-4-(phenylthio)but-2-en-1-ol；trans-4-Phenylthiobuten-(2)-ol-(1)；(2E)-4-(Phenylsulfanyl)but-2-EN-1-OL；(E)-4-phenylsulfanylbut-2-en-1-ol
• CAS: 121666-84-0
• 化学式: C₁₀H₁₂OS
• 分子量: 180.271
• InChiKey: BBGQKCGYUMKLJV-SNAWJCMRSA-N

物化性质

• 沸点：
  297.0±33.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-hydroxy-2-butenyl phenyl sulfide 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到(E)-4-(phenylthio)but-2-enal
  参考文献：
  名称：

  A Versatile and Highly Selective Hypervalent Iodine (III)/2,2,6,6-Tetramethyl-1-piperidinyloxyl-Mediated Oxidation of Alcohols to Carbonyl Compounds

  摘要：

  Catalytic amounts of 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) are used in combination with [bis(acetoxy)iodo]benzene (BAIB) as a stoichiometric oxidant in the conversion of primary and secondary alcohols to carbonyl compounds. This procedure works efficiently at room temperature in almost all common solvents and neat in some cases. This process exhibits a very high degree of selectivity for the oxidation of primary alcohols to aldehydes, without any noticeable overoxidation to carboxyl compounds, and a high chemoselectivity in the presence of either secondary alcohols or of other oxidizable moieties. This procedure allows an easy, convenient, high-yielding method for the oxidation of alcohols starting from commercially available compounds.

  DOI：

  10.1021/jo971046m
• 作为产物：
  描述：

  (E)-3-methoxycarbonylprop-2-enyl phenyl sulfide 在 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 0.5h， 以46%的产率得到(E)-4-hydroxy-2-butenyl phenyl sulfide
  参考文献：
  名称：

  Fe(II)-Catalyzed Imidation of Allyl Sulfides and Subsequent [2,3]-Sigmatropic Rearrangement. Preparation of α-Branched N-tert-Butyloxycarbonyl (Boc)-Protected N-Allylamines

  摘要：

  Allyl aryl sulfides 1 and 5 were shown to undergo an imidation/[2,3]-sigmatropic rearrangement reaction upon treatment with N-tert-butyloxycarbonyl azide (BocN(3)) and catalytic amounts of FeCl2 in CH2Cl2. The N-Boc-protected N-allyl sulfenamides 3 and 21 were obtained in yields between 48 and 75% (12 examples), Whereas the reaction is well suited for the transformation of alpha-unbranched sulfides to a-branched sulfenamides, the enantiomerically pure alpha-branched sulfides 10 and 13 reacted sluggishly. The corresponding sulfenamides 22 and 23 were obtained in only moderate enantiomeric excess (36-39% eel. A reaction mechanism is proposed that postulates the intermediacy of an N-Boc-substituted Fe(IV)-nitrene complex 14 acting as the imidation reagent in the catalytic cycle. Possible side reactions are discussed. The benzenesulfenamides 3 were further converted into N-Boc-N-allylamines 4 by removal of the phenylsulfanyl group. Bu3SnH in benzene was found to be the reagent of choice for the deprotection of alpha-branched amines that bear a secondary allyl substituent (five examples, 71-93% yield). This method failed for the alpha-branched amines 3i-k with a tertiary allyl substituent. The phenylsulfanyl group was finally removed with P(OEt)(3)/NEt3 in CH2Cl2 (three examples, 43-62% yield).

  DOI：

  10.1021/jo991569p

文献信息

• Catalyst-Free Imidation of Allyl Sulfides with Chloramine-T and Subsequent [2,3]-Sigmatropic Rearrangement
  作者：Yubo Jiang、Fanyang Mo、Di Qiu、Chunxiang Kuang、Yan Zhang、Jianbo Wang

  DOI：10.1002/cjoc.201200604

  日期：2012.9

  A facile synthesis of various allyl sulfonamides based on imidation of allyl sulfides with chloramine‐T and subsequent [2,3]‐sigmatropic rearrangement has been achieved without metal catalysts. The reaction completes smoothly within 10 min, providing excellent yields in environment friendly solvent of alcohol. Functional groups such as bromine, hydroxyl, protected amido and aldehyde are tolerant under

  在没有金属催化剂的情况下，已经实现了基于烯丙基硫化物的氯胺-T酰亚胺化和随后的[2,3]-σ重排的轻松合成各种烯丙基磺酰胺的方法。反应在10分钟内顺利完成，在环境友好的乙醇溶剂中提供优异的收率。在这种条件下，溴，羟基，受保护的酰胺基和醛等官能团是可以耐受的。
• Dechalcogenative Allylic Selenosulfide and Disulfide Rearrangements:  Complementary Methods for the Formation of Allylic Sulfides in the Absence of Electrophiles. Scope, Limitations, and Application to the Functionalization of Unprotected Peptides in Aqueous Media
  作者：David Crich、Venkataramanan Krishnamurthy、Franck Brebion、Maheswaran Karatholuvhu、Venkataraman Subramanian、Thomas K. Hutton

  DOI：10.1021/ja072969u

  日期：2007.8.1

  Primary allylic selenosulfates (seleno Bunte salts) and selenocyanates transfer the allylic selenide moiety to thiols giving primary allylic selenosulfides, which undergo rearrangement in the presence of PPh3 with the loss of selenium to give allylically rearranged allyl alkyl sulfides. This rearrangement may be conducted with prenyl-type selenosulfides to give isoprenyl alkyl sulfides. Alkyl secondary

  初级烯丙基硒代硫酸盐（硒代本特盐）和硒氰酸盐将烯丙基硒化物部分转移到硫醇上，产生初级烯丙基硒硫化物，在 PPh3 存在下发生重排，失去硒，得到烯丙基重排的烯丙基烷基硫化物。这种重排可以用异戊二烯基型硒硫化物进行，得到异戊二烯基烷基硫化物。烷基仲和叔烯丙基二硫化物，由硫化物从烯丙基杂芳基二硫化物转移到硫醇形成，在室温下在甲醇乙腈中用 PPh3 处理时发生脱硫烯丙基重排。对于橙花油烷基二硫化物，这种重排提供了一种将法呢基链引入硫醇的无亲电方法。两种重排都与蛋白质氨基酸中发现的全部功能兼容，并且证明脱硫重排在水性介质中起作用，能够衍生化未受保护的肽。还表明，在室温下，在没有膦的情况下，可以通过用哌啶处理或简单地通过在甲醇中回流来诱导烯丙基二硫化物重排。在后面这些条件下，该反应也适用于烯丙基芳基二硫化物，以良好的产率提供烯丙基重排的烯丙基芳基硫化物。还表明，在室温下，在没有膦的情况下，可以通过用哌
• Et₃B-Induced Radical Reaction of 1,3-Diene Monoxide with C₆F₁₃I, PhSH, or Ph₃GeH
  作者：Yoshifumi Ichinose、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1246/cl.1988.1437

  日期：1988.8.5

  Treatment of 3,4-epoxy-1-butene with CgF13I, PhSH, or Ph3GeH in the presence of Et3B provides 4-substituted-2-buten-1-ol in good yield. Et3B–Ph3SnH mediated intramolecular alkylation of 1,3-diene monoxide are also described.

  在有 Et3B 存在的情况下，用 CgF13I、PhSH 或 Ph3GeH 处理 3,4-环氧-1-丁烯，可以得到 4-取代的-2-丁烯-1-醇，收率很高。此外，还介绍了 Et3B-Ph3SnH 介导的 1,3-二烯一氧化物分子内烷基化反应。
• PALLADIUM-CATALYZED COUPLING REACTION OF VINYL EPOXIDES, DIOL ACETONIDES, AND DIOL CARBONATES WITH ORGANOBISMUTH COMPOUNDS
  作者：Suk-Ku Kang、Hyung-Chul Ryu、Young-Taek Hong、Moon-Sung Kim、Sung-Won Lee、Jung-Hee Jung

  DOI：10.1081/scc-100104838

  日期：2001.1

  The palladium-catalyzed arylation reaction of vinyl epoxides with organobismuth compounds afforded the aryl-substituted (E)-allylic alcohols via ring opening of epoxides. Alternatively, the palladium-catalyzed reaction of diol acetonides and carbonates with bismuth derivatives afforded the aryl-substituted diol acetonides and carbonates without ring opening.

  钯催化的乙烯基环氧化物与有机铋化合物的芳基化反应通过环氧化物的开环得到芳基取代的 (E)-烯丙醇。或者，二醇丙酮化物和碳酸酯与铋衍生物的钯催化反应得到芳基取代的二醇丙酮化物和碳酸酯而没有开环。
• Highly diastereoselective ionic/radical domino reactions: single electron transfer induced cyclization of bis-sulfoxides
  作者：Jean-Philippe Goddard、Catherine Gomez、Franck Brebion、Sophie Beauvière、Louis Fensterbank、Max Malacria

  DOI：10.1039/b705284g

  日期：——

  SET oxidation of bis-sulfinyl anions has enabled the uses of bis-sulfinyl radical as a synthetic equivalent of chiral acyl and methylene radicals involved in tandem reactions leading to the enantioselective construction of various carbo- and heterocyclic derivatives.

  双亚磺酰基阴离子的SET氧化使得能够使用双亚磺酰基自由基作为参与串联反应的手性酰基和亚甲基自由基的合成等价物，从而导致各种碳和杂环衍生物的对映选择性结构。