双(甲硫基)乙酸 | 58925-98-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 双(甲硫基)乙酸
• 英文名称: bis(methylthio)acetic acid
• 英文别名: bis-methylsulfanyl-acetic acid；Bis-methylmercapto-essigsaeure；Bis(methylthio)essigsaeure；2,2-Bis(methylsulfanyl)acetic acid
• CAS: 58925-98-7
• 化学式: C₄H₈O₂S₂
• 分子量: 152.238
• InChiKey: AAIKDESBMTXGNW-UHFFFAOYSA-N

物化性质

• 熔点：
  77-79 °C
• 沸点：
  265.8±30.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  87.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  双(甲硫基)乙酸 在 氢氧化钾 、 草酰氯 作用下， 生成 bis(methylthio)acetyl chloride
  参考文献：
  名称：

  A new synthetic entry to pentacyclic Strychnos alkaloids. Total synthesis of (.+-.)-tubifolidine, (.+-.)-tubifoline, and (.+-.)-19,20-dihydroakuammicine

  摘要：

  A new strategy for the synthesis of pentacyclic Strychnos alkaloids has been developed. It consists in the closure of the five-membered E ring by cyclization upon the indole 3-position from a suitably N-substituted tetracyclic system embodying rings ABCD of the alkaloids. Attempts to effect the key cyclization either by Pummerer rearrangement of sulfinylacetamides 4 and 6, from chloroacetamide 12, or from bis(methylthio)acetamide 10b (exocyclic amide carbonyl group) resulted in failure. In the first case dithioacetals 9 and 10, respectively, were formed in good yields. Cyclization from alcohol 13 or from the indole-deactivated acetal 15 and dithiocetal 18 were also unsuccessful: noncyclized products coming from the initially formed oxonium or thionium intermediates 16 were obtained. Cyclization was satisfactorily accomplished in 49% yield by treatment of the N-unsubstituted indole dithioacetal 23 with DMTSF. The resulting pentacycle 25 was converted to 20-deethyltubifolidine (27). A similar treatment from dithioacetal 41a, prepared from the secondary amine 32a, afforded pentacycle 42a, from which the alkaloids tubifoline, tubifolidine, and 19,20-dihydroakuammicine were synthesized.

  DOI：

  10.1021/jo00313a017
• 作为产物：
  描述：

  (甲硫基)乙酸 生成 双(甲硫基)乙酸
  参考文献：
  名称：

  嘌呤，嘧啶和咪唑。第XXXIII部分。5-甲基磺酰基尿苷及其5'-单和焦磷酸酯的合成

  摘要：

  已经制备了5-甲硫基尿酸三-O-苯甲酸酯和5-甲基磺酰基尿苷。后者产生结晶的三乙酸酯和异亚丙基衍生物，当通过不同方法进行磷酸化时，其经由中间体2'，3'-异亚丙基-5-甲基磺酰基尿苷5'-磷酸，产生5-甲基磺酰基尿苷5'-磷酸。将单磷酸酯以各种方式转化为相应的焦磷酸酯。讨论了一些中间体的反应和制备。

  DOI：

  10.1039/j39700002016

文献信息

• Tananger, Arkiv foer Kemi, 1947, vol. 24 A, # 10, p. 4
  作者：Tananger

  DOI：——

  日期：——
• Hellstroem; Holmberg, Arkiv foer Kemi, 1936, vol. 12 A, # 2, p. 6
  作者：Hellstroem、Holmberg

  DOI：——

  日期：——
• AMAT, MERCEDES;LINARES, ANA;BOSCH, JOAN, J. ORG. CHEM., 55,(1990) N6, C. 6299-6312
  作者：AMAT, MERCEDES、LINARES, ANA、BOSCH, JOAN

  DOI：——

  日期：——