2-((4-chlorophenyl)thio)tetrahydro-2H-pyran

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-((4-chlorophenyl)thio)tetrahydro-2H-pyran
• 英文别名: 2-(4-Chlorophenyl)sulfanyloxane
• 化学式: C₁₁H₁₃ClOS
• 分子量: 228.743
• InChiKey: SPZODLZBXOGYJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  四氢吡喃 、 4-氯苯硫酚 在 二叔丁基过氧化物 作用下， 反应 6.0h， 以70%的产率得到2-((4-chlorophenyl)thio)tetrahydro-2H-pyran
  参考文献：
  名称：

  异色满的 C(sp3)-H 键硫醚化的简便方法

  摘要：

  通过在无金属条件下异色满的直接氧化 C(sp 3 )-H 键硫酯化，开发了一种前所未有的 C-S 形成方案。通过绿色、简单和原子经济的方法可以有效地提供一系列异色满衍生物。

  DOI：

  10.1055/s-0034-1380125

文献信息

• Visible-Light-Induced Direct Thiolation at α-C(sp³)–H of Ethers with Disulfides Using Acridine Red as Photocatalyst
  作者：Xianjin Zhu、Xiaoyu Xie、Pinhua Li、Jianqi Guo、Lei Wang

  DOI：10.1021/acs.orglett.6b00304

  日期：2016.4.1

  α-arylthioethers through a visible-light-induced direct thiolation at α-C(sp3)–H of ethers with diaryl disulfides was developed using acridine red as a novel photocatalyst. The reactions occurred at ambient conditions and generated the corresponding products in good to excellent yields, ignoring steric effect of disulfides.

  利用a啶红作为新型光催化剂，开发了一种简单有效的方法，该方法通过可见光诱导的醚与二芳基二硫化物在α-C（sp 3）-H上的直接硫醇化反应制备α-芳基硫醚。该反应在环境条件下发生，并且以高至优异的产率产生了相应的产物，而忽略了二硫化物的空间效应。
• Solvent-Free Anti-Markovnikov Addition of Thiols to Alkenes Using Anhydrous Cerium(III) Chloride as Catalyst
  作者：Claudio Silveira、Samuel Mendes、Francieli Líbero

  DOI：10.1055/s-0029-1219350

  日期：2010.3

  The anti-Markovnikov addition of thiols to alkenes using CeCl3 as catalyst is described. The products were obtained in good to excellent yields. The reaction occurred under solvent-free conditions at room temperature.

  描述了使用CeCl3作为催化剂的硫醇对烯烃的反Markovnikov加成。产品的产率从良好到优异。反应在室温下无溶剂条件下进行。
• Water-Promoted Highly Selective Anti-Markovnikov Addition of Thiols to Unactivated Alkenes
  作者：Brindaban Ranu、Tanmay Mandal

  DOI：10.1055/s-2007-973877

  日期：2007.4

  The highly selective anti-Markovnikov addition of thiols to unactivated alkenes is demonstrated in water at room temperature without any additive. This is a very simple and efficient method for the synthesis of linear thioethers.

  在室温下，无需任何添加剂，在水中实现了高度选择性的抗马尔科夫尼科夫反应，将硫醇添加到未活化的烯烃中。这是一种非常简单且高效的线性硫醚合成方法。
• Visible-light-promoted C(sp³)–H thiolation of aliphatic ethers with thiosulfonates
  作者：Wen-Zhu Bi、Qing-Pu Liu、Chen-Yu Li、Wen-Jie Zhang、Su-Xiang Feng、Yang Geng、Xiao-Lan Chen、Ling-Bo Qu

  DOI：10.1039/d3nj01029e

  日期：——

  A visible-light-promoted direct thiolation of α-C(sp3)–H in ethers with thiosulfonates was developed for the preparation of α-arylthioethers using easily availably Na2-eosin Y and TBHP as a photocatalyst and oxidant. This reaction occurred smoothly under the irradiation of 5 W blue light at room temperature and generated the corresponding products in good to excellent yields.

  使用容易获得的 Na 2 -伊红 Y 和 TBHP 作为光催化剂和氧化剂，开发了可见光促进的 α-C(sp 3 )–H 在醚中与硫代磺酸盐的直接硫醇化，用于制备 α-芳基硫醚。该反应在室温下5W蓝光照射下顺利进行，并以优良的收率生成相应的产物。
• MICROWAVE ACCELERATED TETRAHYDROPYRANYLATION AND DETETRAHYDROPYRANYLATION OF ALCOHOLS, PHENOLS, AND THIOLS CATALYZED BY HYDRATED ZIRCONIA
  作者：Anil S. Gajare、Dhananjay P. Sabde、Murlidhar S. Shingare、Radhika D. Wakharkar

  DOI：10.1081/scc-120004145

  日期：2002.1

  A solvent free and expeditious method for tetrahydropyranylation and detetrahydropyranylation of alcohols, phenols and thiols is described using hydrated zirconia and 3,4-dihydro-2H-pyran (DHP). A comparison of this microwave-accelerated reaction with conventional heating condition is also presented.