2-(1,3-dithian-2-yl)-5-methylthiophene | 154244-29-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-(1,3-dithian-2-yl)-5-methylthiophene
• 英文别名: 2-(5-methyl-2-thienyl)-1,3-dithiane；2-(1,3-Dithian-2-yl)-5-methyl thiophene；2-(5-methylthiophen-2-yl)-1,3-dithiane
• CAS: 154244-29-8
• 化学式: C₉H₁₂S₃
• 分子量: 216.392
• InChiKey: HFEKUDHURMFFFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  78.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2(5H)-呋喃酮 、 2-(1,3-dithian-2-yl)-5-methylthiophene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.75h， 生成 4-<2-(5-methyl-2-thienyl)-1,3-dithial-2-yl>dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Heterolignanolides. Furo- and thieno-analogues of podophyllotoxin and thuriferic acid

  摘要：

  The conjugate addition-alkylation to 5H-furan-2-one followed by cyclization and controlled epimerizations have been applied to the synthesis of new furo- and thieno-lignan analogues. Podophyllotoxin and thuriferic acid heteroanalogues have been obtained by this methodology, as representative members of these families. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00271-x
• 作为产物：
  描述：

  5-甲基-2-噻吩甲醛 、 1,3-丙二硫醇 在 三甲基氯硅烷 作用下， 以 氯仿 为溶剂， 生成 2-(1,3-dithian-2-yl)-5-methylthiophene
  参考文献：
  名称：

  Heterolignanolides. Furo- and thieno-analogues of podophyllotoxin and thuriferic acid

  摘要：

  The conjugate addition-alkylation to 5H-furan-2-one followed by cyclization and controlled epimerizations have been applied to the synthesis of new furo- and thieno-lignan analogues. Podophyllotoxin and thuriferic acid heteroanalogues have been obtained by this methodology, as representative members of these families. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00271-x

文献信息

• Medarde, Manuel; Ramos, Angel C.; Clairac, Rafael Pelaez-Lamamie de, Journal of the Chemical Society. Perkin transactions I, 1994, # 1, p. 45 - 48
  作者：Medarde, Manuel、Ramos, Angel C.、Clairac, Rafael Pelaez-Lamamie de、Caballero, Esther、Feliciano, Arturo San

  DOI：——

  日期：——
• New approach to the synthesis of cyclic 1,3-dithioacetals from thiophene-2-carbaldehydes
  作者：L. K. Papernaya、E. P. Lebanova、E. N. Sukhomasova、A. I. Albanov、E. N. Deryagina

  DOI：10.1134/s1070428002120175

  日期：2006.2

  A highly selective method was developed for preparation of previously unknown 1,3-dithiolanes and 1,3-dithianes by reactions of thiophene-2-carbaldehyde and its analogs with alkanedithiols under the action of trimethylchlorosilane.
• Synthesis and cytotoxic activities of analogues of thuriferic acid
  作者：Blanca Madrigal、Pilar Puebla、Angel Ramos、Rafael Peláez、Dolores Grávalos、Esther Caballero、Manuel Medarde

  DOI：10.1016/s0968-0896(01)00280-2

  日期：2002.2

  Several analogues of thuriferic acid and derivatives, with the 3,4-methylenedioxyphenyl ring replaced by naphthalene, furan, thiophene and carbazole ring systems, have been prepared. The synthetic strategy is based on a conjugate addition alkylation methodology followed by cationic cyclization in order to obtain the isopodophyllone analogues, which are transformed in the thuriferic acids. Their cytotoxic activities against several tumour cells lines are also described. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Heterolignanolides. Furo- and thieno-analogues of podophyllotoxin and thuriferic acid
  作者：Angel C Ramos、Rafael Peláez、Jose Luis López、Esther Caballero、Manuel Medarde、Arturo San Feliciano

  DOI：10.1016/s0040-4020(01)00271-x

  日期：2001.4

  The conjugate addition-alkylation to 5H-furan-2-one followed by cyclization and controlled epimerizations have been applied to the synthesis of new furo- and thieno-lignan analogues. Podophyllotoxin and thuriferic acid heteroanalogues have been obtained by this methodology, as representative members of these families. (C) 2001 Elsevier Science Ltd. All rights reserved.