bis[1,3-S-(N,N-diethylthiocarbamoyl)]-1,3-dideoxyglycerol | 179342-22-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 二硫代氨基甲酸及其衍生物
• 英文名称: bis[1,3-S-(N,N-diethylthiocarbamoyl)]-1,3-dideoxyglycerol
• 英文别名: bis-1,3-S-(N,N-diethyldithiocarbamoyl)-1,3-dideoxyglycerol；[3-(diethylcarbamothioylsulfanyl)-2-hydroxypropyl] N,N-diethylcarbamodithioate
• CAS: 179342-22-4
• 化学式: C₁₃H₂₆N₂OS₄
• 分子量: 354.626
• InChiKey: ANWPTDBVVSOUNK-UHFFFAOYSA-N

物化性质

• 沸点：
  459.015±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.209±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  辛酰氯 、 bis[1,3-S-(N,N-diethylthiocarbamoyl)]-1,3-dideoxyglycerol 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以75%的产率得到2-O-octanoyl-1,3-dideoxy-1,3-di-S-(N,N-diethylthiocarbamoyl)glycerol
  参考文献：
  名称：

  碳水化合物的新型双二硫代氨基甲酸酯衍生物的合成及其对尖孢镰刀菌的抗真菌活性。sp。莉妮。

  摘要：

  合成了具有衍生自具有两个N，N-二乙基二硫代氨基甲酰基的甘油或D-葡萄糖的碳水化合物部分的新型氨基甲酸酯和一系列具有酮或烷基酯的双二硫代氨基甲酸酯。评估了这些新化合物对尖孢镰刀菌f的体外活性。sp。莉妮。一些化合物[双[1,3-S-（N，N-二乙基二硫代氨基甲酰基）]-1，3-二脱氧甘油）和二乙基N，N'-（1,3-二脱氧甘油-1，3-二基）双（ （二硫代氨基甲酸酯）]分别比市售N，N-二乙基二硫代氨基甲酸钠盐和Maneb更具抑制菌丝体生长的活性。讨论了这些新化合物的结构活性。

  DOI：

  10.1021/jf0003698
• 作为产物：
  描述：

  1,3-二氯丙醇 、 N,N-diethyldithiocarbamic acid lithium salt 以 丙酮 为溶剂， 反应 1.0h， 以95%的产率得到bis[1,3-S-(N,N-diethylthiocarbamoyl)]-1,3-dideoxyglycerol
  参考文献：
  名称：

  Synthesis and Antifungal Activity of Novel Bis(dithiocarbamate) Derivatives of Glycerol

  摘要：

  Three bis(dithiocarbamate) derivatives of glycerol were obtained in 30-95% yields by reaction of a dithiocarbamic acid salt with 1,3-dichloro-1,3-dideoxyglycerol. The in vitro antifungal activity of the new compounds was evaluated against Alternaria brassicae, Pseudocercosporella herpotrichoides, Septoria nodorum, and Phytophtora cinnamomi. Some of the compounds displayed greater activity than commercial fungicides. Bis(N,N-diethyldithiacarbamoyl)-1,3-dideoxyglycerol (4) was found to maintain its pesticidal activity up to 24 days in open field tests against A. brassicae.

  DOI：

  10.1021/jf950751y

文献信息

• METHOD FOR PREPARING DITHIOCARBAMATES IN PARTICULAR FROM POLYOLS OF THE GLYCEROL TYPE
  申请人：Jerome Francois

  公开号：US20120264941A1

  公开（公告）日：2012-10-18

  The present invention concerns a method for the synthesis of glycerol dithiocarbamates or bis-dithiocarbamates (GDTCs) in which a reaction medium comprising (1) a carbonate selected from diethyl carbonate, dimethyl carbonate and ethylene or propylene carbonate associated with a glycerol type polyol in the presence of a basic catalyst or (2) a cyclic carbonate comprising five ring members, in a solvent medium, is supplemented with a primary or secondary amine in the presence of carbon disulphide, and the GDTC formed is recovered. In particular, a glycerol type polyol is brought into the presence of diethyl carbonate in the presence of a catalyst, then a primary or secondary amine is added to the reaction medium in the presence of carbon disulphide, and the GDTC formed is recovered. The invention can be used for one-step synthesis of glycerol dithiocarbamates directly from glycerol as the starting material and solvent. This method involves glycerol, diethyl carbonate, carbon disulphide (CS 2 ) and a primary or secondary amine to produce glycerol dithiocarbamates; the glycerol/NaOH phase can be recycled 6 times without a noticeable drop in yield; the ethyl acetate is also recycled after each extraction.

  本发明涉及一种合成甘油二硫代氨基甲酸酯或双硫代氨基甲酸酯（GDTCs）的方法，其中在反应介质中加入（1）选择自乙酸二乙酯、甲酸二甲酯和乙二醇或丙二醇碳酸酯的碳酸盐与一种甘油型多元醇，在碱性催化剂的存在下，或者（2）包含五个环成员的环状碳酸盐，在溶剂介质中，加入一种一次或二次胺和碳二硫化物，然后回收形成的GDTC。特别地，将一种甘油型多元醇与乙酸二乙酯在催化剂的存在下混合，然后在碳二硫化物的存在下向反应介质中加入一种一次或二次胺，最后回收形成的GDTC。该发明可用于直接从甘油作为起始物和溶剂一步合成甘油二硫代氨基甲酸酯。该方法涉及甘油、乙酸二乙酯、碳二硫化物（CS2）和一种一次或二次胺来产生甘油二硫代氨基甲酸酯；甘油/氢氧化钠相可循环使用6次而不会明显降低产率；每次萃取后乙酸乙酯也可回收利用。
• US8772526B2
  申请人：——

  公开号：US8772526B2

  公开（公告）日：2014-07-08
• Synthesis and Antifungal Activity of Novel Bisdithiocarbamate Derivatives of Carbohydrates against <i>Fusarium oxysporum</i> f. sp. <i>l</i><i>ini</i>
  作者：Catherine Rafin、Etienne Veignie、Michel Sancholle、Denis Postel、Christophe Len、Pierre Villa、Gino Ronco

  DOI：10.1021/jf0003698

  日期：2000.11.1

  from glycerol or D-glucose with two N,N-diethyldithiocarbamoyl groups and a series of bisdithiocarbamic esters having a ketone or an alkyl ester have been synthesized. The in vitro activity of these new compounds was evaluated against Fusarium oxysporum f. sp. lini. Some of the compounds [bis[1,3-S-(N,N-diethyldithiocarbamoyl)]-1, 3-dideoxyglycerol) and diethyl N,N'-(1,3-dideoxyglycer-1, 3-diyl)bis(dithiocarbamate)]

  合成了具有衍生自具有两个N，N-二乙基二硫代氨基甲酰基的甘油或D-葡萄糖的碳水化合物部分的新型氨基甲酸酯和一系列具有酮或烷基酯的双二硫代氨基甲酸酯。评估了这些新化合物对尖孢镰刀菌f的体外活性。sp。莉妮。一些化合物[双[1,3-S-（N，N-二乙基二硫代氨基甲酰基）]-1，3-二脱氧甘油）和二乙基N，N'-（1,3-二脱氧甘油-1，3-二基）双（ （二硫代氨基甲酸酯）]分别比市售N，N-二乙基二硫代氨基甲酸钠盐和Maneb更具抑制菌丝体生长的活性。讨论了这些新化合物的结构活性。
• Synthesis and Antifungal Activity of Novel Bis(dithiocarbamate) Derivatives of Glycerol
  作者：Christophe Len、Anne-S. Boulogne-Merlot、Denis Postel、Gino Ronco、Pierre Villa、Christel Goubert、Eric Jeufrault、Bernard Mathon、Hervé Simon

  DOI：10.1021/jf950751y

  日期：1996.1.1

  Three bis(dithiocarbamate) derivatives of glycerol were obtained in 30-95% yields by reaction of a dithiocarbamic acid salt with 1,3-dichloro-1,3-dideoxyglycerol. The in vitro antifungal activity of the new compounds was evaluated against Alternaria brassicae, Pseudocercosporella herpotrichoides, Septoria nodorum, and Phytophtora cinnamomi. Some of the compounds displayed greater activity than commercial fungicides. Bis(N,N-diethyldithiacarbamoyl)-1,3-dideoxyglycerol (4) was found to maintain its pesticidal activity up to 24 days in open field tests against A. brassicae.