(E/Z)-5-phenylthio-4-penten-1-ol | 111341-52-7

• 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/Z)-5-phenylthio-4-penten-1-ol
• 英文别名: 5-(phenylthio)pent-4-en-1-ol；5-(Phenylsulfanyl)pent-4-en-1-ol；5-phenylsulfanylpent-4-en-1-ol
• CAS: 111341-52-7
• 化学式: C₁₁H₁₄OS
• 分子量: 194.298
• InChiKey: PJZRNXUYKKIAOK-UHFFFAOYSA-N

物化性质

• 沸点：
  334.6±34.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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/Z)-5-phenylthio-4-penten-1-ol 在 四氯化碳 、 正丁基锂 、 叔丁基锂 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  1,2-二烷基-1-苯基环戊烷的立体选择性合成，涉及α-硫代烯烃的分子内碳锂化

  摘要：

  由6-甲基硒基-6-苯基-1-苯基硫基-1-庚烯和7-甲基硒基-7合成了2-乙基-1-甲基-1-苯基环戊烷，这是丁基锂促进的相应烯基硒化物的碳环化无法得到的。在所有三个立体异构中心均具有高度立体控制的-苯基-2-苯基硫基-2-辛烯。根据所使用的溶剂，选择性地形成其中甲基和苯硫基甲基彼此为顺式（在THF中）或反式（在戊烷中）的衍生物。

  DOI：

  10.1016/0040-4020(96)00261-x
• 作为产物：
  描述：

  (E)-5-(phenylthio)pent-4-en-1-ol 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 0.75h， 生成 (E/Z)-5-phenylthio-4-penten-1-ol
  参考文献：
  名称：

  Facile synthesis and desulfurization of 5-(phenylthio)pyrano[3,2-c][1]benzopyrans starting from 5-phenylthio-4-penten-1-ols and salicylaldehyde via in situ intramolecular cycloaddition of substituted o-quinonemethides

  摘要：

  5-(Phenylthio)pyrano[3,2-c][1]benzopyrans (6) were successfully synthesized in high yield by the reaction of 5-phenylthio-4-penten-1-ol (5) and salicylardehyde (1) in benzene in the presence of p-toluenesulfonic acid and trimethyl orthoformate. trans,trans-Isomer 6a and cis,cis-isomer 6d were produced as major products from (E)-5 and (Z)-5, respectively. Treatment of 6a with lithium 4,4'-di-tert-butylbiphenyl or Raney Ni (W-4) lead to trans-pyrano[3,2-c][1]benzopyran 4b which is very difficult to make by direct cycloaddition using unsubstituted 4-penten-1-ol (2b). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00236-7

文献信息

• Evolution of a Polyene Cyclization Cascade for the Total Synthesis of (−)-Cyclosmenospongine
  作者：Klaus Speck、Thomas Magauer

  DOI：10.1002/chem.201605029

  日期：2017.1.23

  We report a full account on the development of a unique cationic polyene cyclization for the total synthesis of the tetracyclic meroterpenoid (−)‐cyclosmenospongine. A highly convergent three‐component coupling strategy enabled rapid access to individual cyclization precursors that were tested for their reactivity. The successful transformation generates three rings and sets four consecutive stereocenters

  我们报告了一个完整的发展为四环甲氧萜（-）-cyclosmenospongine的全合成独特的阳离子多烯环化的完整说明。高度收敛的三组分偶联策略使得能够快速访问经过测试其反应性的各个环化前体。成功的转换生成了三个环，并在一次操作中以高效的方式设置了四个连续的立体中心，从而仅给出了十萘烷的反式构架。此外，我们发现烯醇醚的几何形状以及C3和C8的相对构型对于多烯环化的成功至关重要。
• Designed Bifunctional Phosphine Ligand-Enabled Gold-Catalyzed Isomerizations of Ynamides and Allenamides: Stereoselective and Regioselective Formation of 1-Amido-1,3-dienes
  作者：Xingguang Li、Zhixun Wang、Xu Ma、Pei-nian Liu、Liming Zhang

  DOI：10.1021/acs.orglett.7b02624

  日期：2017.11.3

  By using designed biphenyl-2-ylphosphines functionalized with a remote basic groups as ligands, N-alkynyl-o-nosylamides are directly converted to (1E,3E)-1-amido-1,3-dienes with excellent diastereoselectivities under gold catalysis. With allenamides as substrates, the gold-catalyzed isomerizations are high yielding and applicable to a broad substrate scope including various nitrogen protecting groups and exhibit unprecedented (3E)-selectivities for the distal C-C double bond and good regioselectivities. Combining this gold catalysis with one-pot Diels-Alder reactions leads to rapid assembly of valuable bicyclic compounds.
• Stereoselective syntheses of 1,2-dialkyl-1-phenyl cyclopentanes involving intramolecular carbolithiation of α-thioalkenes
  作者：Alain Krief、Benoît Kenda、Bruno Remacle

  DOI：10.1016/0040-4020(96)00261-x

  日期：1996.5

  2-Ethyl-1-methyl-1-phenyl cyclopentane, unavailable by butyllithium-promoted carbocyclisation of the corresponding alkenyl selenide, has been synthesized from 6-methylseleno-6-phenyl-1-phenylthio-1-heptene and 7-methylseleno-7-phenyl-2-phenylthio-2-octene with high stereocontrol at all the three stereogenic centers. Depending upon the solvent used, the derivative in which the methyl- and the phenylthiomethyl

  由6-甲基硒基-6-苯基-1-苯基硫基-1-庚烯和7-甲基硒基-7合成了2-乙基-1-甲基-1-苯基环戊烷，这是丁基锂促进的相应烯基硒化物的碳环化无法得到的。在所有三个立体异构中心均具有高度立体控制的-苯基-2-苯基硫基-2-辛烯。根据所使用的溶剂，选择性地形成其中甲基和苯硫基甲基彼此为顺式（在THF中）或反式（在戊烷中）的衍生物。
• Facile synthesis and desulfurization of 5-(phenylthio)pyrano[3,2-c][1]benzopyrans starting from 5-phenylthio-4-penten-1-ols and salicylaldehyde via in situ intramolecular cycloaddition of substituted o-quinonemethides
  作者：Hidekazu Miyazaki、Yoshinari Honda、Kiyoshi Honda、Seiichi Inoue

  DOI：10.1016/s0040-4039(00)00236-7

  日期：2000.4

  5-(Phenylthio)pyrano[3,2-c][1]benzopyrans (6) were successfully synthesized in high yield by the reaction of 5-phenylthio-4-penten-1-ol (5) and salicylardehyde (1) in benzene in the presence of p-toluenesulfonic acid and trimethyl orthoformate. trans,trans-Isomer 6a and cis,cis-isomer 6d were produced as major products from (E)-5 and (Z)-5, respectively. Treatment of 6a with lithium 4,4'-di-tert-butylbiphenyl or Raney Ni (W-4) lead to trans-pyrano[3,2-c][1]benzopyran 4b which is very difficult to make by direct cycloaddition using unsubstituted 4-penten-1-ol (2b). (C) 2000 Elsevier Science Ltd. All rights reserved.