苯基(1-苯基丁-3-烯-2-基)硫烷 | 117785-40-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 苯基(1-苯基丁-3-烯-2-基)硫烷
• 英文名称: phenyl(1-phenylbut-3-en-2-yl)sulfane
• 英文别名: 4-phenyl-3-(phenylthio)-1-butene；3-phenylthio-4-phenyl-1-butene；1-Phenylbut-3-en-2-ylsulfanylbenzene
• CAS: 117785-40-7
• 化学式: C₁₆H₁₆S
• 分子量: 240.369
• InChiKey: GZQXVINWMZNRFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  苯基(1-苯基丁-3-烯-2-基)硫烷 在 环戊二烯钛 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以46%的产率得到4-苯基-1-丁烯
  参考文献：
  名称：

  烯丙基硫的脱硫钛化。区域和非对映选择性制备均烯丙基醇

  摘要：

  通过二氯化钛茂与2当量的反应制得的具有低价有机钛物种的烯丙基硫的连续处理方法。丁基锂和醛得到高产率和高区域选择性和非对映选择性的均烯丙基醇。

  DOI：

  10.1016/0040-4039(95)00068-n
• 作为产物：
  描述：

  苯硫酚 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 8.5h， 生成 苯基(1-苯基丁-3-烯-2-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

• The Magnesium−Ene Cyclization Stereochemically Directed by an Allylic Oxyanionic Group and Its Application to a Highly Stereoselective Synthesis of (±)-Matatabiether. Allylmagnesium Compounds by Reductive Magnesiation of Allyl Phenyl Sulfides¹
  作者：Dai Cheng、Shirong Zhu、Zhifang Yu、Theodore Cohen

  DOI：10.1021/ja0029782

  日期：2001.1.1

  more easily prepared in a connective fashion than the usual allyl halide precursor. Since the presence of lithium ions encourages undesirable proton transfer to the cyclized organometallic and is detrimental to the stereochemical control, the conversion of the allylic thioether to the allylmagnesium utilizes a lithium-free method involving direct reductive magnesiation in the presence of the magnesium-anthracene

  由烯丙基含氧阴离子基团立体化学引导的镁-烯环化的第一个例子通过双环萜烯基二醚 10 的高度立体选择性合成证明。该合成方法特别有价值，不仅因为立体化学控制和通用性引入产物中的羟基，也是因为烯丙基镁的前体是烯丙基苯基硫醚，它比通常的烯丙基卤化物前体更稳定，更容易以连接方式制备。由于锂离子的存在会促进不希望的质子转移到环化有机金属，并且不利于立体化学控制，
• 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：——