1-甲基肼-1-二硫代羧酸甲酯 | 20184-94-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫基化合物
• 中文名称: 1-甲基肼-1-二硫代羧酸甲酯
• 英文名称: N-methyl-hydrazinecarbodithioic acid methyl ester
• 英文别名: methyl 1-methylhydrazine carbodithioate；S-methyl 2-methyldithiocarbazate；N-methyl-S-methyldithiocarbazate；2-methyldithiocarbazic acid methyl ester；2-N-methyl-S-methyldithiocarbazate；2-Methyl-dithiocarbazidsaeure-methylester；methyl 1-methyl-1-hydrazinecarbodithioate；S-methyl-N-methyl-dithiocarbazate；methyl 2-methyldithiocarbazate；Hydrazinecarbodithioic acid, 1-methyl-, methyl ester；methyl N-amino-N-methylcarbamodithioate
• CAS: 20184-94-5
• 化学式: C₃H₈N₂S₂
• 分子量: 136.242
• InChiKey: QCEOBXKEQKMIAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  86.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  1-甲基肼-1-二硫代羧酸甲酯 、 二溴三苯基膦 在 三乙胺 作用下， 以 苯 为溶剂， 反应 16.0h， 以61%的产率得到methyl 2-methyl-3-(triphenylphosphoranylidene)dithiocarbazate
  参考文献：
  名称：

  Synthesis of 1,2,4-Triazole and 1,3,4-Thiadiazole Derivatives from Methyl 2-Methyldithiocarbazate and Heterocumulenes

  摘要：

  甲基2-甲基二硫代卡巴胺1与二芳基碳二亚胺反应生成4-芳基-3-芳胺基-1-甲基-5-硫酮-4,5-二氢-1H-1,2,4-三唑3。化合物1还能与异硫氰酸酯反应，生成相应的5-芳胺基-3-甲基-2-硫酮-2,3-二氢-1,3,4-噻二唑6。1的3-三苯基膦亚胺衍生物与芳香异氰酸酯反应，生成中离子安缩-2-芳胺基-4-甲基-5-甲硫基-1,3,4-噻二唑锍氢氧化物10。由1和异氰酸酯可得的甲基3-氨基羰基-2-甲基二硫代卡巴胺11在氯磺酰反应下发生环化，生成1,3,4-噻二唑衍生物12或1,2,4-三唑衍生物13。

  DOI：

  10.1055/s-1989-27431
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 肼 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以85%的产率得到1-(5-Benzylamino-3-morpholino-1 H-1,2,4-triazol-1-yl)carbothiohydrazide
  参考文献：
  名称：

  Barkoczy, Jozsef; Reiter, Jozsef, Journal of Heterocyclic Chemistry, 1992, vol. 29, p. 1677 - 1683

  摘要：

  DOI：

文献信息

• New thiadiazoles and their use as phosphodiesterase-7 inhibitors
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP1193261A1

  公开（公告）日：2002-04-03

  The invention provides 1,3,4-thiadiazoles having the following formula (I): in which, R1 is alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, cycloalkenyl, aryl, heteroaryl or a polycyclic group, optionally substituted, R2 is alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, cycloalkenyl or aryl optionally substituted, R3 is X2-R'3, in which X2 is a binding group and R'3 is cycloalkyl, heterocycloalkyl, cycloalkenyl, aryl, heteroaryl, or a polycyclic group; optionally substituted, or their pharmaceutically acceptable derivatives, the process for their preparation and their use for the manufacture of a medicament for the treatment of disorders for which a treatment by a PDE7 inhibitor is relevant.

  该发明提供具有以下式（I）的1,3,4-噻二唑： 其中， R1是烷基，烯基，炔基，环烷基，杂环烷基，环烯基，芳基，杂芳基或多环基团，可选择性取代， R2是烷基，烯基，炔基，环烷基，杂环烷基，环烯基或芳基，可选择性取代， R3是X2-R'3，其中X2是一个结合基团，R'3是环烷基，杂环烷基，环烯基，芳基，杂芳基或多环基团；可选择性取代，或它们的药学上可接受的衍生物， 它们的制备方法及其用于制备治疗PDE7抑制剂相关疾病的药物的用途。
• Discovery of thiadiazoles as a novel structural class of potent and selective PDE7 inhibitors. Part 1: Design, synthesis and structure–activity relationship studies
  作者：Fabrice Vergne、Patrick Bernardelli、Edwige Lorthiois、Nga Pham、Emmanuelle Proust、Chrystelle Oliveira、Abdel-Kader Mafroud、Frederique Royer、Roger Wrigglesworth、Jennifer Schellhaas、Mark Barvian、François Moreau、Moulay Idrissi、Anita Tertre、Bernadette Bertin、Magali Coupe、Patrick Berna、Patricia Soulard

  DOI：10.1016/j.bmcl.2004.07.008

  日期：2004.9

  The synthesis and SAR studies of a series of structurally novel small molecule inhibitors of PDE7 are discussed. The best compounds from the series displayed low nanomolar inhibitory activity and are selective versus PDE4.

  讨论了一系列结构新颖的PDE7小分子抑制剂的合成和SAR研究。该系列中最好的化合物显示出较低的纳摩尔抑制活性，并且相对于PDE4具有选择性。
• A Convenient Synthesis of 2-Alkylthio-4,5-dihydro-5-methoxythiazoles
  作者：Kee-Jung Lee、Jae Uk Jeong、Dae Ock Choi、Seong Heon Kim、Hokoon Park

  DOI：10.1055/s-1991-26504

  日期：——

  A series of 2-alkylthio-4,5-dihydro-5-methoxythiazoles 3 were prepared by thermal or diethyl ether-boron trifluoride mediated intramolecular cyclization of the corresponding N-(2,2-dimethoxyethyl)dithiocarbamic acid esters 2. Methyl N-(2,2-dimethoxyethyl)dithiocarbamate (2b) and 4,5-dihydro-5-methoxy-2-methylthiothiazole (3b) were converted by a two-step sequence to methyl 2-methyl-3-thioxo-1,2,3,4-tetrahydro-1,2,4-triazine-4-carbodithioate (6).

  一系列2-烷硫基-4,5-二氢-5-甲氧基噻唑3通过相应的N-(2,2-二甲氧基乙基)二硫代氨基甲酸酯2的热或二乙醚-三氟化硼介导的分子内环化反应制备而成。甲基N-(2,2-二甲氧基乙基)二硫代氨基甲酸酯(2b)和4,5-二氢-5-甲氧基-2-甲基硫基噻唑(3b)通过两步序列转化为甲基2-甲基-3-硫酮-1,2,3,4-四氢-1,2,4-三嗪-4-羰二硫代酸酯(6)。
• Unexpected transalkylation on 3-alkyl-2-alkylthio-1,3,4-thiadiazolium-5-thiolates: A computational and experimental mechanistic study
  作者：Arturo Espinosa、Rafaela García、Pedro Molina、Alberto Tárraga

  DOI：10.1039/b923243e

  日期：——

  5-Alkylthio-3-methyl-2-thioxo-1,3,4-thiadiazolines have been obtained on heating alkyl 1-methyl-1-hydrazinecarbodithioates with CS2. A DFT-based computational mechanistic study suggests an initial pseudopericyclic [1,4]H shift as a key step, as well as the intermediacy of the otherwise expected isomers 2-alkylthio-3-methyl-1,3,4-thiadiazolium-5-thiolates, from which the final products are formed by

  通过用CS 2加热1-甲基-1-肼碳二硫代烷基酯，获得了5-烷硫基-3-甲基-2-硫代氧杂1,3,4-噻二唑啉。基于DFT的计算机理研究表明，初始的伪周环[1,4] H位移是关键步骤，以及其他预期的异构体2-烷硫基-3-甲基-1,3,4-噻二唑-5的中间体-硫醇盐，通过逐步的S，S-烷基转移反应形成最终产物。
• Thiadiazoles and oxadiazoles and their use as phosphodiesterase-7 inhibitors
  申请人：——

  公开号：US20030045557A1

  公开（公告）日：2003-03-06

  The invention provides 1,3,4-thiadiazoles and 1,3,4-oxadiazoles having the following Formula I: 1 in which, Y is S or O, R 1 is alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, cycloalkenyl, aryl, heteroaryl or a polycyclic group, optionally substituted, R 2 is alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, cycloalkenyl or aryl optionally substituted, R 3 is X 2 —R′ 3 , in which X 2 is a binding group and R′ 3 is cycloalkyl, heterocycloalkyl, cycloalkenyl, aryl, heteroaryl, or a polycyclic group; optionally substituted, or their pharmaceutically acceptable derivatives, a compound of Formula I, for their preparation, and processes for pharmaceutical compositions containing methods of using the compounds for the treatment of disorders for which a treatment by a PDE7 inhibitor is relevant.

  该发明提供具有以下式I的1,3,4-噻二唑和1,3,4-氧二唑：其中，Y为S或O，R1为烷基、烯烃基、炔烃基、环烷基、杂环烷基、环烯基、芳基、杂芳基或多环基，可选地取代，R2为烷基、烯烃基、炔烃基、环烷基、杂环烷基、环烯基或芳基，可选地取代，R3为X2—R′3，其中X2为结合基团，R′3为环烷基、杂环烷基、环烯基、芳基、杂芳基或多环基；可选地取代，或其药学上可接受的衍生物，式I的化合物，用于它们的制备，以及含有该化合物的制药组合物的处理方法，用于治疗需要通过PDE7抑制剂进行治疗的疾病。

表征谱图