1,2-(methylenedioxy)-3-methoxy-4-<(1,3-propylenedithio)methyl>benzene | 163779-32-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1,2-(methylenedioxy)-3-methoxy-4-<(1,3-propylenedithio)methyl>benzene
• 英文别名: 5-(1,3-Dithian-2-yl)-4-methoxy-1,3-benzodioxole
• CAS: 163779-32-6
• 化学式: C₁₂H₁₄O₃S₂
• 分子量: 270.373
• InChiKey: SHOQCKPGWVFBMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1,2-(methylenedioxy)-3-methoxy-4-<(1,3-propylenedithio)methyl>benzene 在 氢氧化钾 、 sodium tetrahydroborate 、 正丁基锂 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 (R)-4-[2-(4-Methoxy-benzo[1,3]dioxol-5-yl)-[1,3]dithian-2-yl]-dihydro-furan-2-one
  参考文献：
  名称：

  Synthesis and Cytotoxicity of Novel Lignans

  摘要：

  In this study the syntheses of 11 novel lignans are described. Their cytotoxicities are studied in GLC(4), a human small cell lung carcinoma cell line, using the microculture tetrazolium (MTT) assay. Ten of these compounds were substituted with a menthyloxy group on the 5-position of the lactone. These compounds can easily be prepared in (novel) 'one-pot', three- or four-step syntheses. In addition, methods for controlling the stereogenic centers are described. Furthermore, five naturally occurring podophyllotoxin-related compounds were tested. The cytotoxicities of all lignan compounds, and of three non-lignan intermediates originating from the syntheses, were compared with the clinically applied anticancer agents etoposide, teniposide, and cisplatin. Most compounds showed moderate to high activities against GLC(4), and two of the compounds containing a menthyloxy group showed activities comparable to the reference cytotoxic agents.

  DOI：

  10.1021/jm00012a010
• 作为产物：
  描述：

  4-甲氧基-1,3-苯并二氧戊环-5-甲醛 、 1,3-propanedithiol 在 盐酸 作用下， 以 氯仿 为溶剂， 以98%的产率得到1,2-(methylenedioxy)-3-methoxy-4-<(1,3-propylenedithio)methyl>benzene
  参考文献：
  名称：

  Mallaiah, M.; Hazra, B. G.; Das, K. G., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 5, p. 434 - 435

  摘要：

  DOI：