2-(4-methoxyphenyl)methyl-1,3-dithiane | 74447-45-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-methoxyphenyl)methyl-1,3-dithiane
• 英文别名: 2-(4-methoxybenzyl)-1,3-dithiane；2-(4-methoxybenzyl)-1,3-dithian；2-[(4-methoxyphenyl)methyl]-1,3-dithiane
• CAS: 74447-45-3
• 化学式: C₁₂H₁₆OS₂
• 分子量: 240.39
• InChiKey: FOUQTKRRDHYJOU-UHFFFAOYSA-N

物化性质

• 沸点：
  374.5±27.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)methyl-1,3-dithiane 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 ammonium cerium(IV) nitrate 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 5.22h， 生成 2-(p-methoxyphenyl)ethyl toluene-p-sulphonate
  参考文献：
  名称：

  Battersby; Chrystal; Staunton, Journal of the Chemical Society. Perkin transactions I, 1980, vol. 1, p. 31 - 42

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-丙二硫醇 、 4-甲氧基苯乙醛 在 三氟化硼乙醚 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 14.0h， 以91%的产率得到2-(4-methoxyphenyl)methyl-1,3-dithiane
  参考文献：
  名称：

  Chemical Synthesis of Coelenterazine and Its Analogs: New Route toward Four Segment-Couplings

  摘要：

  A novel and improved synthetic route includes four segment-couplings toward coelenterazine and its analogs as luminescent molecules. Regio- and chemo-selective cross coupling reactions using palladium catalysts with 5-iodo-3-bromo-2-aminopyrazine have enabled providing various aminopyrazine derivatives having different substituents. The improved synthesis of coelenterazine and its analogs employed advanced condensation with the aminopyrazines using various keto-acetal segments, which resulted in much higher yields to give the final imidazopyrazinone heterocycles than the previous method using keto-aldehydes.

  DOI：

  10.3987/com-12-s(n)85

文献信息

• Suzuki–Miyaura coupling for general synthesis of dehydrocoelenterazine applicable for 6-position analogs directing toward bioluminescence studies
  作者：Wong Phakhodee、Mitsuko Toyoda、Chun-Ming Chou、Nisachon Khunnawutmanotham、Minoru Isobe

  DOI：10.1016/j.tet.2010.12.001

  日期：2011.2

  Synthesis of coelenterazine analogs is in recent demand to supply more luminescent compounds with reasonable stability as substrate for the photoprotein manipulated in a living cells or particular organelle. There are limited methods for the synthesis of 6-substituted coelenterazine due to the route and instability of the compounds under the existing conditions. This paper describes six examples including Suzuki-Miyaura cross coupling reaction with reactive triflate (unstable) and stable tosylate intermediates of the imidazo[1,2-a]pyrazin-3-one. Five examples of 2-amino-3-benzyl-5-O-Tf-pyrazine are also discussed. The product coelenterazine analogs are obtained in the form of dehydrocoelenterazine, which is the substrate of a squid photoprotein, symplectin. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of Disubstituted Dithioethers: <i>tert</i>-Butoxide Promoted Elimination/Ring Opening of 1,3-Dithianes Followed by Palladium-Catalyzed C–S Bond Formation
  作者：Nissa Abidi、Jason R. Schmink

  DOI：10.1021/acs.joc.5b00547

  日期：2015.4.17

  We report the tandem base-promoted elimination/ring-opening of 2-benzyl-1,3-dithianes with subsequent cross coupling of the pendent thiol with a range of aryl bromides. A simple Pd(OAc)(2)/Xantphos catalyst system affects this new reaction and is compatible with a wide range of functional groups, including heteroaromatic coupling partners. The transformation proceeds in good to excellent yields (6999%) and exhibits strong stereoselectivity, forming the E-alkene as the major diastereomer. This new methodology provides access to nonsymmetric propylene styryl/aryl dithioethers, a previously undisclosed motif.