(E)-3-methyl-4-(4-methylphenyl)sulfanylbut-2-en-1-ol | 175691-51-7

• 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)-3-methyl-4-(4-methylphenyl)sulfanylbut-2-en-1-ol
• CAS: 175691-51-7
• 化学式: C₁₂H₁₆OS
• 分子量: 208.324
• InChiKey: KIAPNPBIOIAYSN-YRNVUSSQSA-N

物化性质

• 沸点：
  324.2±37.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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)-3-methyl-4-(4-methylphenyl)sulfanylbut-2-en-1-ol 在 oxone^<*> 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 51.5h， 生成 Toluene-4-sulfonateallyl-dibenzyl-[(E)-3-methyl-4-(toluene-4-sulfonyl)-but-2-enyl]-ammonium;
  参考文献：
  名称：

  Influence of quaternization or coordination of nitrogen with a Lewis acid upon the diastereoselectivity of 5-exo ring closure of β-aminoalkyl radicals

  摘要：

  Two methodologies, likely to enhance the diastereoselectivity of sulfonyl radical mediated cyclization of dienes 8 and 11, were investigated. Quaternization provided the expected result whatever the nature of the radical accepting. double bond, so did complexation of 11 with BF3 or AlMe3. A more strongly coordinating reagent like BH3 was necessary to improve selectivity in the case of 8. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00772-8
• 作为产物：
  描述：

  4-氯-3-甲基丁-2-烯-1-醇乙酸酯 在 lithium aluminium tetrahydride 、 sodium ethanolate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 (E)-3-methyl-4-(4-methylphenyl)sulfanylbut-2-en-1-ol
  参考文献：
  名称：

  Influence of quaternization or coordination of nitrogen with a Lewis acid upon the diastereoselectivity of 5-exo ring closure of β-aminoalkyl radicals

  摘要：

  Two methodologies, likely to enhance the diastereoselectivity of sulfonyl radical mediated cyclization of dienes 8 and 11, were investigated. Quaternization provided the expected result whatever the nature of the radical accepting. double bond, so did complexation of 11 with BF3 or AlMe3. A more strongly coordinating reagent like BH3 was necessary to improve selectivity in the case of 8. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00772-8

文献信息

• Synthesis of (±)- and (−)-botryodiplodin using stereoselective radical cyclizations of acyclic esters and acetals
  作者：Robert Nouguier、Stéphane Gastaldi、Didier Stien、Michèle Bertrand、Félix Villar、Olivier Andrey、Philippe Renaud

  DOI：10.1016/j.tetasy.2003.06.004

  日期：2003.10

  Three different routes for the stereoselective synthesis of botryodiplodin have been investigated. The intramolecular allylation of acetals proved to be unsatisfactory due to unstable intermediates and poor stereocontrol. Zard intramolecular radical allylation of a 2-iodopropionate derivative allows the development of an expeditious synthesis of racemic botryodiplodin. The relative configuration within

  已经研究了用于葡萄孢菌素的立体选择性合成的三种不同途径。缩醛的分子内烯丙基化由于不稳定的中间体和差的立体控制而被证明是不令人满意的。2-碘代丙酸酯衍生物的Zard分子内自由基烯丙基化可以快速发展外消旋的葡萄孢单倍体。最终产品中的相对构型已通过去质子-再质子化步骤进行了校正。接下来研究了烯丙基溴缩醛的环化反应，证明其对于合成外消旋和对映体纯的葡萄球菌双孢菌素是令人满意的。通过环化宝石-二溴化物，然后立体选择性地还原由此形成的环状一溴化物，实现了良好的立体控制。
• Intramolecular radical allylation with allylic sulfones— A synthesis of (±)-botryodiplodin
  作者：Robert Nouguier、Ste´phane Gastaldi、Didier Stien、Miche`le Bertrand、Philippe Renaud

  DOI：10.1016/s0040-4039(99)00486-4

  日期：1999.4

  (±)-botryodiplodin (1). Several pathways, involving 5-exo-trig ring closure onto allylic sulfones, have been investigated. The iodine atom transfer methodology allowed the preparation of the desired skeleton through intramolecular addition of an α-alkoxycarbonyl radical to the double bond of the appropriate allylic ethyl sulfone. Subsequent deprotonation and kinetic reprotonation led to the key precursor14 with

  异丙烯基5元环缩醛或内酯是（±）-botryodiplodin（1）的潜在前体。已经研究了几种途径，包括在烯丙基砜上的5- exo-trig闭环。碘原子转移方法允许通过将α-烷氧基羰基分子内加成到适当的烯丙基乙基砜的双键上来制备所需的骨架。随后的去质子化和动力学再质子化导致具有高立体选择性的关键前体14。图选项
• 4-Isopropenyl-3-tosylmethyl pyrrolidines through radical cyclizations of 4-aza-1,6-dienes - an approach to kainic acids
  作者：M.-P Bertrand、S Gastaldi、R Nouguier

  DOI：10.1016/0040-4039(96)00006-8

  日期：1996.2

  The cyclofunctionalization of 4-aza-1,6-dienes 1 and 2 - bearing a prenyl chain - via the radical addition of PhSeTs (4) has been investigated as a potential route to 4-isopropenyl-3-tosylmethylpyrrolidines. Since the oxidative elimination of the resulting selenides afforded mainly the undesired olefinic regioisomer, an alternative pathway via the rearrangement of allylic sulfones 10–11, was applied

  已经研究了通过PhSeTs（4）的自由基加成反应使带有氮杂烯基链的4-氮杂-1,6-二烯基1和2的环官能团化成为4-异丙烯基-3-甲苯磺酰基甲基吡咯烷酮的潜在途径。由于所得硒化物的氧化消除主要提供了不希望的烯烃区域异构体，因此采用了通过烯丙基砜10-11重排的替代途径，并以高收率提供了目标杂环。12 a，b是海藻酸的潜在前体。