methyl 4-(dimethylamino)benzodithioate | 6120-82-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: methyl 4-(dimethylamino)benzodithioate
• 英文别名: Methyl 4-(dimethylamino)benzenecarbodithioate
• CAS: 6120-82-7
• 化学式: C₁₀H₁₃NS₂
• 分子量: 211.352
• InChiKey: KMSOGTNIHILHJR-UHFFFAOYSA-N

物化性质

• 沸点：
  325.0±44.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  60.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-(dimethylamino)benzodithioate 在 sodium ethanolate 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 Dimethyl 10-[4-(dimethylamino)phenyl]-11-thia-8,9-diazatricyclo[5.4.0.04,8]undeca-2,5,9-triene-1,2-dicarboxylate
  参考文献：
  名称：

  Preparation of New Nitrogen-Bridged Heterocycles. 43.¹ Synthesis and Reaction of 5aH-Pyrido[1,2-d][1,3,4]thiadiazepine Derivatives

  摘要：

  Reactions of some 1-pyridinio- and 1-(4-methylpyridinio)(arenethiocarbonyl) with dimethyl acetylenedicarboxylate in chloroform afforded neither the expected dimethyl 2-aryl-5aH-pyrido-[1,2-d][1,3,4]thiadiazepine-4,5-dicarboxylates nor their intramolecular Diels-Alder adducts, but gave novel rearranged products, dimethyl 4-aryl-5-thia-2,3-diazatricyclo[4.3.2.0(2,7)]undeca-3,8,10-triene-6,11-dicarboxylates in low to moderate yields. On the other hand, similar reactions of 1-(3-methylpyridinio)- and 1-(2-methylquinolinio)(arenethiocarbonyl)amidates with the same reagent provided 1:1 primary adducts, dimethyl 2-aryl-6-methyl-5aH-pyrido[1,2-d][1,3,4]thiadiazepine-4,5-dicarboxylates and dimethyl 2-aryl-5a-methyl-5aH-[1,3,4]thiadiazepino[4,5-alpha]quinoline-4,5-dicarboxylates, respectively.

  DOI：

  10.1021/jo971066o
• 作为产物：
  描述：

  碘甲烷 、 4-[[4-(二甲氨基)苯基]硫代甲基]-吗啉 生成 methyl 4-(dimethylamino)benzodithioate
  参考文献：
  名称：

  Mayer,R. et al., Chemische Berichte, 1966, vol. 99, p. 1393 - 1413

  摘要：

  DOI：

文献信息

• Synthesis of 2,4,5-Trisubstituted Oxazoles with Complementary Regioselectivity from α-Oxoketene Dithioacetals and β-(Methylthio)-β-(het)aryl-2-propenones
  作者：Siripuram Vijay Kumar、Anand Acharya、Hiriyakkanavar Ila

  DOI：10.1021/acs.joc.8b00900

  日期：2018.6.15

  An efficient protocol for the synthesis of 2,5-substituted 4-acyloxazoles and the related 2,4-substituted 5-acyloxazoles with complementary regioselectivity from the corresponding α-oxoketene dithioacetals or β-(het)aryl/(methylthio)enone precursors has been reported. In the first protocol, the α-oxoketene dithioacetals or β-(methylthio)enones were converted to the corresponding α-bromo-β-(methylthio)enones

  从相应的α-氧杂环丁烯二硫缩醛或β-（杂）芳基/（甲硫基）烯酮前体合成具有互补区域选择性的2,5-取代的4-酰基恶唑和相关的2,4-取代的5-酰基恶唑的有效方案是被报道。在第一个方案中，将α-氧杂环丁烯二硫缩醛或β-（甲硫基）烯酮转化为相应的α-溴-β-（甲硫基）烯酮，然后用各种伯酰胺将这些中间体进行铜催化的中间/分子内环化，得到2- （杂）芳基/烷基-4-（杂）芳酰基-5-（甲硫基）/（杂）芳基恶唑是通过酰胺中间体同时形成C4-N和C5-O键。在第二种方法中 首先，将起始的α-氧杂环丁烯二硫缩醛或β-（甲硫基）-β-（杂）芳基酮与各种伯酰胺进行碱诱导的共轭加成消除反应，以提供β-芳烯酰胺，随后碘将其催化的分子内氧化C–H官能化/ CO键的形成，以优异的收率提供了相应的区域异构体2-（杂）芳基/烷基-4-（甲硫基）/（杂）芳基-5-（杂）芳酰基恶唑。该方法也已扩展到合成区域异构的4-或5-
• Single-Pot Preparation of 4-Amino-2-(het)aryl-5-Substituted Thiazoles Employing Functionalized Dithioesters as Thiocarbonyl Precursors
  作者：Anusha Avadhani、Pethaperumal Iniyavan、Yogendra Kumar、Hiriyakkanavar Ila

  DOI：10.1021/acs.joc.1c00616

  日期：2021.6.18

  4-amino-2-(het)aryl/alkyl-5-functionalized thiazoles has been disclosed, utilizing aryl/heteroaryl/alkyl dithioesters as thiocarbonyl coupling partners in a modified Thorpe–Ziegler type cyclization. The reaction proceeds at room temperature, under mild conditions, in excellent yields, displaying broad functional group compatibility at 2 and 5 positions of thiazoles. This synthetic strategy has been further

  已经公开了一种有效的、面向多样性的、4-氨基-2-（杂）芳基/烷基-5-官能化噻唑的一锅反应，利用芳基/杂芳基/烷基二硫酯作为改性索普-齐格勒型中的硫代羰基偶联伙伴环化。该反应在室温、温和条件下以优异的产率进行，在噻唑的 2 位和 5 位显示出广泛的官能团相容性。这种合成策略已进一步扩展用于高产率的一锅法构建两种高效微管蛋白聚合抑制剂，即 2-(het)aryl-4-amino-5-(3,4,5-trimethoxyaroyl) thiazoles .
• Reaction of 1,3-Bis(het)arylmonothio-1,3-diketones with Sodium Azide: Regioselective Synthesis of 3,5-Bis(het)arylisoxazoles via Intramolecular N–O Bond Formation
  作者：Mary Antony P、Gantala L. Balaji、Pethaperumal Iniyavan、Hiriyakkanavar Ila

  DOI：10.1021/acs.joc.0c02216

  日期：2020.12.4

  An efficient new synthesis of 3,5-bis(het)arylisoxazoles, involving the reaction of 1,3-bis(het)arylmonothio-1,3-diketones with sodium azide in the presence of IBX catalyst, has been reported. The reaction proceeds at room temperature in high yields and is applicable to a broad range of substrates including the synthesis of 5-methyl-3-arylisoxazoles, a key subunit present in several β-lactamase-resistant

  据报道，在IBX催化剂存在下，一种有效的新的3,5-双（杂）芳基异恶唑合成涉及1,3-双（杂）芳基单硫-1,3-二酮与叠氮化钠的反应。该反应在室温下以高收率进行，适用于多种底物，包括5-甲基-3-芳基异恶唑的合成，5-甲基-3-芳基异恶唑是几种抗β-内酰胺酶的抗生素中存在的关键亚基。已经提出了形成异恶唑的可能机理。还通过使相应的1-（杂）芳基-1-（甲硫基）-4-（杂）亚芳基-丁-1-烯-反应而合成了一些5-苯乙烯基/芳基丁二烯基-3-（杂）芳基异恶唑。在较高温度下与叠氮化钠共3个。β-酮二硫酯与叠氮化钠的反应显示出可提供高产率的β-酮腈。
• Sequential One-Pot Synthesis of Tri- and Tetrasubstituted Thiophenes and Fluorescent Push–Pull Thiophene Acrylates Involving (Het)aryl Dithioesters as Thiocarbonyl Precursors
  作者：Anand Acharya、G. Parameshwarappa、B. Saraiah、H. Ila

  DOI：10.1021/jo502429c

  日期：2015.1.2

  An efficient, one-pot three component synthesis of highly functionalized tri- and tetrasubstituted thiophenes has been reported involving (het)aryl dithioesters as thiocarbonyl precursors. Thus, sequential base mediated condensation of readily available (het)aryl active methylene ketones with (het)aryl dithioesters followed by S-alkylation of the resulting enethiolate salts with activated halomethylene

  已经报道了一种高效，一锅三组分的高度官能化的三和四取代噻吩的合成方法，其中涉及（杂）芳基二硫代酯作为硫代羰基前体。因此，容易获得的（杂）芳基活性亚甲基酮与（杂）芳基二硫代酯的顺序碱介导的缩合，然后用活化的卤代亚甲基化合物对所得的烯硫醇盐进行S-烷基化，同时S-烷基化的化合物的分子内醇醛缩合型提供了取代基。噻吩的收率极高。通过使用溴巴豆酸酯作为活化的亚甲基烷基化剂，该方法也已扩展到合成高荧光推挽式取代的噻吩-5-丙烯酸酯。
• Synthesis of Substituted Benzo[<i>b</i>]thiophenes via Base-Promoted Domino Condensation–Intramolecular C–S Bond Formation
  作者：Yogendra Kumar、Hiriyakkanavar Ila

  DOI：10.1021/acs.orglett.1c00085

  日期：2021.3.5

  A novel synthesis of 2,3-substituted benzothiophenes is reported, involving a tandem base-mediated condensation of o-iodoarylacetonitriles/acetates/ketones with (hetero)aryldithioesters and an intramolecular C–S bond formation. The reaction affords diversely substituted benzothiophenes and heterofused thiophenes in excellent yields.

  据报道，有一种新颖的2，3-取代的苯并噻吩的合成方法，涉及到邻位碘代芳基乙腈/乙酸酯/酮与（杂）芳基二硫代酸酯的串联碱基介导的缩合反应以及分子内C-S键的形成。该反应以优异的产率提供了各种取代的苯并噻吩和杂稠的噻吩。