1-thiophenyl-2-[5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl]ethyne | 1398115-51-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1-thiophenyl-2-[5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl]ethyne
• 英文别名: 1,1,4,4-Tetramethyl-6-(2-phenylsulfanylethynyl)-2,3-dihydronaphthalene；1,1,4,4-tetramethyl-6-(2-phenylsulfanylethynyl)-2,3-dihydronaphthalene
• CAS: 1398115-51-9
• 化学式: C₂₂H₂₄S
• 分子量: 320.499
• InChiKey: SPLCJIZODYYUQG-UHFFFAOYSA-N

物化性质

• 沸点：
  437.5±55.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  1-thiophenyl-2-[5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl]ethyne 在 盐酸 、 1,2-双(二苯基膦)乙烷氯化镍 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 10.84h， 生成 芳维甲酸
  参考文献：
  名称：

  Synthesis of arotinoid acid and temarotene using mixed (Z)-1,2-bis(organylchalcogene)-1-alkene as precursor

  摘要：

  An efficient and novel total synthesis of the two bioactive retinoids temarotene and arotinoid acid (TTNPB) is described. The key steps in this process include the regio and stereoselective hydrotelluration of thioacetylene 9 and Te/Li transmetalation of mixed (Z)-1,2-bis(organylchalcogene)-1-alkene (Z)-3. The subsequent reaction involving the beta-phenylthio vinyl lithiated intermediate 10 with dimethyl sulfate gave the (E)-vinyl sulfide 11. The Ni+2 cross-coupling of 11 with the corresponding phenylzinc bromide and p-oxazoline phenylzinc bromide 12 afforded the respective temarotene 2 and retinoid-oxazoline substituted 13. Finally, compound 13 was deprotected with HCl to furnish arotinoid acid (TTNPB) 1. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.092
• 作为产物：
  描述：

  2,5-二氯-2,5-二甲基己烷 在 aluminum (III) chloride 、 copper(l) iodide 、 正丁基锂 、 sodium hydride 、 三乙胺 、 palladium dichloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 1-thiophenyl-2-[5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl]ethyne
  参考文献：
  名称：

  Synthesis of arotinoid acid and temarotene using mixed (Z)-1,2-bis(organylchalcogene)-1-alkene as precursor

  摘要：

  An efficient and novel total synthesis of the two bioactive retinoids temarotene and arotinoid acid (TTNPB) is described. The key steps in this process include the regio and stereoselective hydrotelluration of thioacetylene 9 and Te/Li transmetalation of mixed (Z)-1,2-bis(organylchalcogene)-1-alkene (Z)-3. The subsequent reaction involving the beta-phenylthio vinyl lithiated intermediate 10 with dimethyl sulfate gave the (E)-vinyl sulfide 11. The Ni+2 cross-coupling of 11 with the corresponding phenylzinc bromide and p-oxazoline phenylzinc bromide 12 afforded the respective temarotene 2 and retinoid-oxazoline substituted 13. Finally, compound 13 was deprotected with HCl to furnish arotinoid acid (TTNPB) 1. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.092

文献信息

• Synthesis of arotinoid acid and temarotene using mixed (Z)-1,2-bis(organylchalcogene)-1-alkene as precursor
  作者：Palimécio G. Guerrero、Paulo R. de Oliveira、Adriano C.M. Baroni、Francisco A. Marques、Ricardo Labes、Gabriela R. Hurtado、Miguel J. Dabdoub

  DOI：10.1016/j.tetlet.2012.07.092

  日期：2012.9

  An efficient and novel total synthesis of the two bioactive retinoids temarotene and arotinoid acid (TTNPB) is described. The key steps in this process include the regio and stereoselective hydrotelluration of thioacetylene 9 and Te/Li transmetalation of mixed (Z)-1,2-bis(organylchalcogene)-1-alkene (Z)-3. The subsequent reaction involving the beta-phenylthio vinyl lithiated intermediate 10 with dimethyl sulfate gave the (E)-vinyl sulfide 11. The Ni+2 cross-coupling of 11 with the corresponding phenylzinc bromide and p-oxazoline phenylzinc bromide 12 afforded the respective temarotene 2 and retinoid-oxazoline substituted 13. Finally, compound 13 was deprotected with HCl to furnish arotinoid acid (TTNPB) 1. (c) 2012 Elsevier Ltd. All rights reserved.