(4-甲基-1-苯基戊-3-烯-2-基)(苯基)硫烷 | 117785-43-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: (4-甲基-1-苯基戊-3-烯-2-基)(苯基)硫烷
• 英文名称: (4-methyl-1-phenylpent-3-en-2-yl)(phenyl)sulfane
• 英文别名: (4-Methyl-1-phenylpent-3-en-2-yl)sulfanylbenzene
• CAS: 117785-43-0
• 化学式: C₁₈H₂₀S
• 分子量: 268.423
• InChiKey: QSCBBTXPJDUFTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4-甲基-1-苯基戊-3-烯-2-基)(苯基)硫烷 在 二氯二茂钛 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以68%的产率得到(E)-(4-methylpenta-1,3-dien-1-yl)benzene
  参考文献：
  名称：

  Unprecedented Elimination of Conjugated Phenylthioether Groups by Low-Valent Titanocene

  摘要：

  发现了第一个利用低价二茂钛的硫醚消除反应。该反应在温和条件下发生，并立体定向地产生多种二烯和苯乙烯。我们的数据表明，这种新反应涉及二茂钛二聚中间体作为负责这种消除的反应物。

  DOI：

  10.1055/s-0030-1259009
• 作为产物：
  描述：

  二苯二硫醚 在 吡啶 、 正丁基锂 、 三丁基膦 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 生成 (4-甲基-1-苯基戊-3-烯-2-基)(苯基)硫烷
  参考文献：
  名称：

  Synthesis of Allylsilanes by Reductive Lithiation of Thioethers

  摘要：

  Although much work in reductive lithiation has been done, the utilization of allylthioethers bearing various substituents to prepare allylsilanes has not been explored. The main reason clearly stems from the anticipated lack of regioselectivity. We describe herein the first study on the regioselectivity of the reductive silylation involving dissymmetric allylthioethers. We surveyed a broad spectrum of parameters and showed that this process displays a great dependence of the reaction conditions. We also discovered that an electron transporter, DBB or naphthalene, can cleave THF at room temperature by sonication, to generate a strong base, 4-lithiobutoxide. This feature was successfully exploited to the straightforward synthesis of bis-silanes in one pot. Examples are provided for maximizing both the chemical yield and the regioselectivity of the reductive silylation through the tuning of the reaction conditions. By changing these conditions, several allylsilanes can be selectively synthesized from one thioether.

  DOI：

  10.1021/jo049237u

文献信息

• Desulfurizative Stannylation of Allyl Sulfide Using Tributylstannyllithium
  作者：Takeshi Takeda、Shinji Ogawa、Nagaaki Ohta、Tooru Fujiwara

  DOI：10.1246/cl.1987.1967

  日期：1987.10.5

  Allylstannanes were prepared by the reaction of allyl sulfides with tributylstannyllithium in the presence of CuBr and HMPA in good yields.

  烯丙基锡烷是通过烯丙基硫化物与三丁基锡锂在 CuBr 和 HMPA 存在下以良好产率反应制备的。
• TAKEDA, TAKESHI;OGAWA, SHINJI;OHTA, NAGAAKI;FUJIWARA, TOORU, CHEM. LETT.,(1987) N 10, 1967-1970
  作者：TAKEDA, TAKESHI、OGAWA, SHINJI、OHTA, NAGAAKI、FUJIWARA, TOORU

  DOI：——

  日期：——
• Synthesis of Allylsilanes by Reductive Lithiation of Thioethers
  作者：Stéphane Streiff、Nigel Ribeiro、Laurent Désaubry

  DOI：10.1021/jo049237u

  日期：2004.10.1

  Although much work in reductive lithiation has been done, the utilization of allylthioethers bearing various substituents to prepare allylsilanes has not been explored. The main reason clearly stems from the anticipated lack of regioselectivity. We describe herein the first study on the regioselectivity of the reductive silylation involving dissymmetric allylthioethers. We surveyed a broad spectrum of parameters and showed that this process displays a great dependence of the reaction conditions. We also discovered that an electron transporter, DBB or naphthalene, can cleave THF at room temperature by sonication, to generate a strong base, 4-lithiobutoxide. This feature was successfully exploited to the straightforward synthesis of bis-silanes in one pot. Examples are provided for maximizing both the chemical yield and the regioselectivity of the reductive silylation through the tuning of the reaction conditions. By changing these conditions, several allylsilanes can be selectively synthesized from one thioether.
• Unprecedented Elimination of Conjugated Phenylthioether Groups by Low-Valent Titanocene
  作者：Nigel Ribeiro、Ludivine Fetzer、Stéphane Streiff、Laurent Désaubry

  DOI：10.1055/s-0030-1259009

  日期：2010.12

  The first thioether elimination reaction utilizing a low-valent titanocene has been discovered. This reaction occurs under mild conditions and affords stereospecifically a variety of dienes and styrenes. Our data suggest that this new reaction involves an intermediate of dimerization of titanocene as the reactant responsible for this elimination.

  发现了第一个利用低价二茂钛的硫醚消除反应。该反应在温和条件下发生，并立体定向地产生多种二烯和苯乙烯。我们的数据表明，这种新反应涉及二茂钛二聚中间体作为负责这种消除的反应物。