2-(2-(4-methoxybenzyl)-1,3-dithian-2-yl)-1,3-dioxolane | 1268631-75-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2-(4-methoxybenzyl)-1,3-dithian-2-yl)-1,3-dioxolane
• 英文别名: 2-[2-[(4-Methoxyphenyl)methyl]-1,3-dithian-2-yl]-1,3-dioxolane；2-[2-[(4-methoxyphenyl)methyl]-1,3-dithian-2-yl]-1,3-dioxolane
• CAS: 1268631-75-9
• 化学式: C₁₅H₂₀O₃S₂
• 分子量: 312.454
• InChiKey: VNYNMFJDQSAESB-UHFFFAOYSA-N

物化性质

• 沸点：
  452.8±45.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  78.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-(4-methoxybenzyl)-1,3-dithian-2-yl)-1,3-dioxolane 在 盐酸 、 manganese(IV) oxide 、 N-氯代丁二酰亚胺 、 水 、 silver nitrate 作用下， 以 1,4-二氧六环 、 乙醚 、 乙醇 、 水 、 乙腈 为溶剂， 反应 4.58h， 生成 (Z)-8-benzyl-2-(4-methoxybenzylidene)-3-oxo-2,3-dihydroimidazo[1,2-a]pyrazin-6-yl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Suzuki–Miyaura coupling for general synthesis of dehydrocoelenterazine applicable for 6-position analogs directing toward bioluminescence studies

  摘要：

  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.

  DOI：

  10.1016/j.tet.2010.12.001
• 作为产物：
  描述：

  2-(4-methoxyphenyl)methyl-1,3-dithiane 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 18.5h， 生成 2-(2-(4-methoxybenzyl)-1,3-dithian-2-yl)-1,3-dioxolane
  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.
• Chemical Synthesis of Coelenterazine and Its Analogs: New Route toward Four Segment-Couplings
  作者：Minoru Isobe、Chun-Ming Chou、Yu-Wen Tung、Meng-I Ling、Diana Chan、Wong Phakhodee

  DOI：10.3987/com-12-s(n)85

  日期：——

  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.