trans-3-(methylthio) methylene-2-pyrrolidinethione | 128463-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫代内酰胺类
• 英文名称: trans-3-(methylthio) methylene-2-pyrrolidinethione
• 英文别名: 3-(E)-(methylthio)methylene-2-pyrrolidinethione；E-raphanusanin；trans-raphanusanin；(E)-3-(Methylthiomethylene)pyrrolidine-2-thione；(3E)-3-(methylsulfanylmethylidene)pyrrolidine-2-thione
• CAS: 128463-44-5
• 化学式: C₆H₉NS₂
• 分子量: 159.276
• InChiKey: BVYUPEKENRMVJK-SNAWJCMRSA-N

物化性质

• 沸点：
  243.9±50.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-3-(methylthio) methylene-2-pyrrolidinethione 以 甲醇 为溶剂， 反应 6.0h， 生成 cis-3-(methylthio) methylene-2-pyrrolidinethione
  参考文献：
  名称：

  Structure-activity relationships of raphanusanins and their analogues

  摘要：

  The structure-activity relationship of raphanusanins A and B {(3R*,6R*)-and (3R*,6S*)-3-[methoxy(methylthio)methyl]-2-pyrrolidinethione, respectively} and their analogues has been studied for the inhibition of the growth of lettuce hypocotyls and Amaranthus roots. Pyrrolidinethione compounds showed higher activity than pyrrolidinones. The presence of a methoxy(methylthio)methyl group or of a methylthiomethylene moiety at C-3 of pyrrolidinethione was a dominant factor for higher activity. The bis(methylthio)methyl derivative also gave a similar inhibitory activity. It was established that the active sites in the chemical structure of the raphanusanins and their analogues were the thioamide moiety at C-2 of the skeleton and a methoxy(methylthio)methyl, bis(methylthio)methyl, or methylthiomethylene group in the C-3 position of the side chain.

  DOI：

  10.1016/0031-9422(93)85140-m
• 作为产物：
  描述：

  4-methylthio-3-butenyl isothiocyanate 在 aluminum oxide 作用下， 以 二氯甲烷 为溶剂， 反应 92.0h， 以41.9%的产率得到trans-3-(methylthio) methylene-2-pyrrolidinethione
  参考文献：
  名称：

  Synthesis and bioactivity of 4-methylthio-3-butenylisothiocyanate and raphanusanin, phototropism-regulating substances of radish hypocotyls

  摘要：

  DOI：

  10.1016/j.tetlet.2021.153025

文献信息

• Chemical studies on 4-methylthio-3-butenyl isothiocyanate from roots of japanese radish(Raphanus sativus L.) in connection with raphanusanins, phototropism-regulating substances of radish hypocotyls
  作者：Seji Kosemura、Shosuke Yamamura、Koji Hasegawa

  DOI：10.1016/0040-4039(93)85107-8

  日期：1993.1

  4-Methylthio-3-butenyl isothiocyanate as the direct precursor of raphanusanins has been isolated from the commercially available radish (Raphanus sativus L.), and some chemical studies on 4-methylthio-3-butenyl isothiocyanate (MTB-ITC) have been carried out, where it has been spontaneously converted into raphanusanins, phototropism-regulating substances of radish hypocotyls, in MeOH-H2O as well as

  已经从市售萝卜（Raphanus sativus L.）中分离出了作为萝卜硫烷素直接前体的4-甲硫基-3-丁烯基异硫氰酸酯，并对4-甲硫基-3-丁烯基异硫氰酸酯（MTB-ITC）进行了一些化学研究。然后，在MeOH-H 2 O以及H 2 O溶液中，它被自发地转化为萝卜甜菊素，萝卜下胚轴的向光性调节物质。
• Matsuoka, Hiroki; Toda, Yoshinori; Yanagi, Kenji, Bioscience, Biotechnology and Biochemistry, 1997, vol. 61, # 12, p. 2109 - 2112
  作者：Matsuoka, Hiroki、Toda, Yoshinori、Yanagi, Kenji、Takahashi, Asaka、Yoneyama, Koichi、Uda, Yasushi

  DOI：——

  日期：——