2-methyl-5-(phenylthio)tetrahydrofuran | 146450-16-0

• 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-methyl-5-(phenylthio)tetrahydrofuran
• 英文别名: 2-Methyl-5-phenylsulfanyloxolane
• CAS: 146450-16-0
• 化学式: C₁₁H₁₄OS
• 分子量: 194.298
• InChiKey: VONXCPDVTDBMGG-UHFFFAOYSA-N

物化性质

• 沸点：
  297.6±33.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 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

• 作为反应物：
  描述：

  2-methyl-5-(phenylthio)tetrahydrofuran 在 叔丁基锂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 5-<6-(4'-methyl-2',6',7'-trioxabicyclo<2.2.2>oct-1'-yl)hexyl>-2-methyl-2,3-dihydrofuran
  参考文献：
  名称：

  Synthesis of trans olefins by a nickel-catalyzed reduction of enol ethers. A formal, total synthesis of (.+-.)-recifeiolide

  摘要：

  DOI：

  10.1021/jo00057a055
• 作为产物：
  描述：

  5-(phenylthio)pentan-2-ol 在 N-氯代丁二酰亚胺 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 8.0h， 生成 2-methyl-5-(phenylthio)tetrahydrofuran
  参考文献：
  名称：

  Applications of highly enantioenriched alcohols bearing a phenylthio group in the preparation of ring compounds. The two-pot synthesis of an enantiopure spiroacetal pheromone bearing three chiral centers

  摘要：

  The new chiron (S)-6-phenylthio-2-hexanol (3) was prepared in high enantiomeric excess by baker's yeast reduction of the corresponding ketone. Enantioenriched alcohols 1, 2 and 3, prepared previously by a similar procedure, or their racemic counterparts, were transformed into ring closed compounds 5-methyl-2-(phenylthio)tetrahydrofuran (9), 6-methyl-2-(phenylthio)tetrahydropyran (10), 2-methyl-1-phenylsulfonyl cyclopropane (14), cyclobutane (15), cyclopentane (16), and a bee pheromone, (2S,6R,8S)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane (20). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00635-2

文献信息

• Two-flask preparation of .alpha.-lithio cyclic ethers from .gamma.- and .delta.-lactones. Reductive lithiation as a route, via radical intermediates, to axial 2-lithiotetrahydropyrans and their equilibration to the equatorial isomers
  作者：Theodore Cohen、Ming Teh Lin

  DOI：10.1021/ja00316a060

  日期：1984.2

  Application a la synthese du rose oxyde et de perhydro furannes, -pyrannes et -chromannes substitues en 2

  应用 a la synthese du rose oxyde et de perhydrofuranes, -pyrannes et -chromannes substitues en 2
• Metal-Free Oxidative C(sp³)–H Bond Thiolation of Ethers with Disulfides
  作者：Sheng-rong Guo、Yan-qin Yuan、Jian-nan Xiang

  DOI：10.1021/ol402281f

  日期：2013.9.20

  A novel method for the preparation of alkyl aryl sulfides through direct oxidation thiolation of commercial ethers with diaryl disulfides using di-tert-butyl peroxide (DTBP) as the oxidant without a metal catalyst was established. The C(sp3)–H bond in various ethers was successfully converted into a C–S bond, and the corresponding sulfides were achieved with moderate to high yields.

  建立了一种新的方法，该方法通过使用二叔丁基过氧化物（DTBP）作为氧化剂，在不使用金属催化剂的情况下，用二芳基二硫化物直接氧化商业化的醚与二芳基二硫化物来制备烷基芳基硫化物。在各种醚中的C（sp 3）-H键成功地转化为C-S键，并以中等至高产率获得了相应的硫化物。
• 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。
• Metal-free and site-selective α-C–H functionalization of tetrahydrofuran enabled by the photocatalytic generation of bromine radicals
  作者：Can-Ming Zhu、Rong-Bin Liang、Yonghong Xiao、Wei Zhou、Qing-Xiao Tong、Jian-Ji Zhong

  DOI：10.1039/d2gc03347j

  日期：——

  A simple and inherent green photocatalytic approach using commercially available and cheap ⁿBu₄NBr with 4-CzIPN was reported to effectively initiate the site-selective α-C(sp³)-H activation of tetrahydrofuran for C-S and C-C cross-couplings.

  一种简单且固有的绿色光催化方法，利用商业可得且价格便宜的nBu4NBr和4-CzIPN，能够有效地启动四氢呋喃的位点选择性α-C(sp3)-H活化，用于C-S和C-C交叉偶联反应。
• Photoinduced C(sp³)–H Chalcogenation of Amide Derivatives and Ethers via Ligand-to-Metal Charge-Transfer
  作者：Ben Niu、Krishnakumar Sachidanandan、Maria Victoria Cooke、Taylor E. Casey、Sébastien Laulhé

  DOI：10.1021/acs.orglett.2c01505

  日期：2022.7.1

  A photoinduced, iron(III) chloride-catalyzed C–H activation of N-methyl amides and ethers leads to the formation of C–S and C–Se bonds via a ligand-to-metal charge transfer (LMCT) process. This methodology converts secondary and tertiary amides, sulfonamides, and carbamates into the corresponding amido-N,S-acetal derivatives in good yields. Mechanistic work revealed that this transformation proceeds

  N-甲基酰胺和醚的光诱导、氯化铁(III)催化的C-H活化导致通过配体到金属电荷转移(LMCT)过程形成C-S和C-Se键。该方法以良好的收率将仲酰胺和叔酰胺、磺酰胺和氨基甲酸酯转化为相应的酰胺基-N,S-缩醛衍生物。机理工作表明，这种转变是通过涉及氯自由基中间体的氢原子转移（HAT）进行的。