(E)-1-phenyl-6-tosylhex-5-en-3-ol | 497154-78-6

• 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-phenyl-6-tosylhex-5-en-3-ol
• 英文别名: (E)-6-(4-methylphenyl)sulfonyl-1-phenylhex-5-en-3-ol
• CAS: 497154-78-6
• 化学式: C₁₉H₂₂O₃S
• 分子量: 330.448
• InChiKey: QGOLIPAAZLCZMO-PJQLUOCWSA-N

物化性质

• 沸点：
  552.9±50.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 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-phenyl-6-tosylhex-5-en-3-ol 在 苯基锂 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (E)-5-hydroxy-1,1-dimethyl-7-phenyl-2-(toluene-4-sulfonyl)hept-2-enyl benzoate
  参考文献：
  名称：

  Tandem Conjugate Addition−Elimination for the Diastereoselective Synthesis of 4E-Alkenyl syn-1,3-Diols

  摘要：

  We have developed a tandem conjugate addition-elimination sequence for the diastereoselective synthesis of protected allylic syri-1,3-diols, starting from vinyl sulfones. The sulfonyl group was then reduced with sodium amalgam to furnish the E-olefin as the major isomer. This method was applied to the synthesis of a trisubstituted alkene modeling the C21-C25 fragment of Dolabelide C.

  DOI：

  10.1021/ol701624y
• 作为产物：
  描述：

  p-toluenesulfonyl iodide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 (E)-1-phenyl-6-tosylhex-5-en-3-ol
  参考文献：
  名称：

  保护的合成顺式通过分子内共轭加成到乙烯基砜1,3-二醇

  摘要：

  描述了通向砜9a – c的捷径。这些合成子包含一个顺式-1,3-二醇基序是用于Dolabelides的C16-C24片段的模型化合物。亚苄基保护基可以区域选择性还原，得到β-羟基砜10a – b。还报道了将这些底物衍生的二价阴离子与醛和酮进行Julia偶联的首次尝试。

  DOI：

  10.1016/s0040-4039(02)01796-3

文献信息

• Synthesis of protected syn 1,3-diols by intramolecular conjugate addition to vinyl sulfones
  作者：Laurence Grimaud、Delphine Rotulo、Rafael Ros-Perez、Ludivine Guitry-Azam、Joëlle Prunet

  DOI：10.1016/s0040-4039(02)01796-3

  日期：2002.10

  A short route to sulfones 9a–c is described. These synthons encompassing a syn 1,3-diol motif are model compounds for the C16–C24 fragment of Dolabelides. The benzylidene protecting group can be reduced regioselectively to furnish β-hydroxysulfones 10a–b. First attempts of Julia coupling of the dianions derived from these substrates with aldehydes and ketones are also reported.

  描述了通向砜9a – c的捷径。这些合成子包含一个顺式-1,3-二醇基序是用于Dolabelides的C16-C24片段的模型化合物。亚苄基保护基可以区域选择性还原，得到β-羟基砜10a – b。还报道了将这些底物衍生的二价阴离子与醛和酮进行Julia偶联的首次尝试。
• “<i>Syn-Effect</i>” in the Desulfonylation Reaction of<i>α</i>,<i>α</i>-Dialkylated (<i>E</i>)-Allylic Sulfones
  作者：Atsushi Shibayama、Tetsuya Nakamura、Takahiro Asada、Takehiko Shintani、Yutaka Ukaji、Hideki Kinoshita、Katsuhiko Inomata

  DOI：10.1246/bcsj.70.381

  日期：1997.2

  It was found that the desulfonylation reaction of α,α-dialkylated (E)-allylic sulfones with a base preferentially affords the sterically unfavorable (Z)-alkadienes. The relative degree of the “syn-effect”, which is herein defined as an effect which stabilizes the syn-conformation, leading to (Z)-products, in the transition state against the steric hindrance, was revealed for various substituents at the δ-position of the (E)-allylic sulfones to be as follows: RO– >> CH3– > RS– > –CH2– > (CH3)2CH– >> (CH3)3C– > C6H5–. This finding is in accord with a previously found tendency in the conversion of (E)-vinylic sulfones to the corresponding allylic sulfones under basic conditions.

  研究发现，α,α-二烷基化(E)-烯丙基砜与碱的脱磺化反应优先产生立体上不利的(Z)-烷二烯。(E)-烯丙基砜的 δ 位上的不同取代基所产生的 "合成效应 "的相对程度如下：RO- >> CH3- >> CH4- >> CH5- >> CH6- >> CH7- >> CH8-RO->>CH3->RS->-CH2->(CH3)2CH->>(CH3)3C->C6H5-。这一发现与之前发现的(E)-乙烯砜在碱性条件下转化为相应的烯丙基砜的趋势一致。
• Diastereoselective synthesis of trifluoromethylated 1,3-dioxanes by intramolecular oxa-Michael reaction
  作者：Liliana Becerra-Figueroa、Elodie Brun、Michael Mathieson、Louis J. Farrugia、Claire Wilson、Joëlle Prunet、Diego Gamba-Sánchez

  DOI：10.1039/c6ob02333a

  日期：——

  A highly diastereoselective synthesis of trifluoromethylated 1,3-dioxanes is described. The reaction proceeds by an addition/oxa-Michael sequence and works efficiently under mild reaction conditions, with a good substrate scope and acceptable to good yields.

  描述了三氟甲基化的1，3-二恶烷的高度非对映选择性的合成。该反应以加成/氧杂-迈克尔序列进行，并且在温和的反应条件下有效地进行，具有良好的底物范围和可接受的良好收率。
• Water-Compatible Synthesis of 2-Trifluoromethyl-1,3-Dioxanes
  作者：Liliana Becerra-Figueroa、Alexander F. Tiniakos、Joëlle Prunet、Diego Gamba-Sánchez

  DOI：10.1002/ejoc.201801367

  日期：2018.12.31

  A water-compatible method for the diastereoselective synthesis of 2-trifluormethyl-1,3-dioxanes is described. The reaction proceeds under mild reaction conditions using simple inorganic bases; it has a very good substrate scope and can be performed with different Michael acceptors. Additionally, the reaction products can be further functionalized, showing an excellent perspective for future applications

  描述了一种用于非对映选择性合成 2-trifluormethyl-1,3-dioxanes 的水相容方法。反应在温和的反应条件下使用简单的无机碱进行；它具有非常好的底物范围，可以使用不同的迈克尔受体进行。此外，反应产物可以进一步功能化，为未来的应用展示了极好的前景。
• Tandem Conjugate Addition−Elimination for the Diastereoselective Synthesis of 4<i>E</i>-Alkenyl <i>syn</i>-1,3-Diols
  作者：Delphine Rotulo-Sims、Joëlle Prunet

  DOI：10.1021/ol701624y

  日期：2007.10.1

  We have developed a tandem conjugate addition-elimination sequence for the diastereoselective synthesis of protected allylic syri-1,3-diols, starting from vinyl sulfones. The sulfonyl group was then reduced with sodium amalgam to furnish the E-olefin as the major isomer. This method was applied to the synthesis of a trisubstituted alkene modeling the C21-C25 fragment of Dolabelide C.