[methylthio-2H3]-3-(methylthio)propionic acid methyl ester | 710354-48-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [methylthio-2H3]-3-(methylthio)propionic acid methyl ester
• 英文别名: Propanoic acid, 3-(methyl-d3-thio)-, methyl ester；methyl 3-(trideuteriomethylsulfanyl)propanoate
• CAS: 710354-48-6
• 化学式: C₅H₁₀O₂S
• 分子量: 137.175
• InChiKey: DMMJVMYCBULSIS-BMSJAHLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [methylthio-2H3]-3-(methylthio)propionic acid methyl ester 、 2-萘基三氟甲烷磺酸 在 palladium(II) trifluoroacetate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 以94 %的产率得到2-(trideuteromethylthio)naphthalene
  参考文献：
  名称：

  稳健的 d3-甲基硫醇化试剂的设计、合成和应用†

  摘要：

  巧妙地配制了一种具有广谱的氘代甲基硫醇化试剂，命名为DMTP。这种新型试剂可以通过市售的 3-硫代丙酸甲酯和 CD 3 I 的简单组合来高效生产。这种新型 SCD 3试剂与烷基碘、苄基氯、芳基卤 (I, Br) 等亲电试剂表现出优异的反应活性和芳基三氟甲磺酸酯，导致氘含量高（99% D）。代表性的氘化甲硫基生物分子，例如磺胺氟草胺，已被合成用于药物发现和开发。

  DOI：

  10.1002/cjoc.202300349
• 作为产物：
  描述：

  氘代碘甲烷 、 3-巯基丙酸甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以88 %的产率得到[methylthio-2H3]-3-(methylthio)propionic acid methyl ester
  参考文献：
  名称：

  稳健的 d3-甲基硫醇化试剂的设计、合成和应用†

  摘要：

  巧妙地配制了一种具有广谱的氘代甲基硫醇化试剂，命名为DMTP。这种新型试剂可以通过市售的 3-硫代丙酸甲酯和 CD 3 I 的简单组合来高效生产。这种新型 SCD 3试剂与烷基碘、苄基氯、芳基卤 (I, Br) 等亲电试剂表现出优异的反应活性和芳基三氟甲磺酸酯，导致氘含量高（99% D）。代表性的氘化甲硫基生物分子，例如磺胺氟草胺，已被合成用于药物发现和开发。

  DOI：

  10.1002/cjoc.202300349

文献信息

• Glucosinolate biosynthesis: demonstration and characterization of the condensing enzyme of the chain elongation cycle in Eruca sativa
  作者：K Falk

  DOI：10.1016/j.phytochem.2004.02.021

  日期：2004.4

  Glucosinolates are a group of sulfur-rich thioglucoside natural products common in the Brassicaceae and related plant families. The first phase in the formation of many glucosinolates involves the chain extension of the amino acid methionine. Additional methylene groups are inserted into the side chain of methionine by a three-step elongation cycle involving 2-oxo acid intermediates. This investigation demonstrated the first step of this chain elongation cycle in a partially-purified preparation from arugula (Eruca sativa). The 2-oxo acid derived from methionine, 4-methylthio-2-oxobutanoic acid, was shown to condense with acetyl-CoA to form 2-(2'-methylthioethyl)malate. The catalyst, designated as a 2-(omega-methylthioalkyl)malate synthase, belongs to a family of enzymes that mediate the condensation of acyl-CoAs with 2-oxo acids, including citrate synthase of the citric acid cycle, and 2-iso-propylmalate synthase of leucine biosynthesis. The 2-(omega-methylthioalkyl)malate synthase studied here shares properties with other enzymes of this class, but appears chromatographically distinct and is found only in extracts of plant species producing glucosinolates from chain-elongated methionine derivatives. Although the principal glucosinolates of arugula are formed from methionine that has undergone two rounds of chain elongation to form dihomomethionine, studies with substrates and substrate analogs of different chain lengths showed that the isolated enzyme is responsible only for the condensation step of the first round of elongation. (C) 2004 Elsevier Ltd. All rights reserved.
• Design, Synthesis and Application of a Robust <scp><i>d</i>₃‐Methylthiolating</scp> Reagent^†
  作者：Yanyang Zhang、Yishuo Ren、Jian Zhang、Shaoli Liu、Yahui Li

  DOI：10.1002/cjoc.202300349

  日期：2023.11.15

  can be produced with high efficiency through the simple combination of commercially available methyl 3-thiopropanoate and CD3I. This novel SCD3 reagent exhibits excellent reactivity with electrophiles such as alkyl iodides, benzyl chlorides, aryl halides (I, Br) and aryl triflates, resulting in high levels of deuterium content (99% D). Representative deuterated methylthiolated biomolecules, such as

  巧妙地配制了一种具有广谱的氘代甲基硫醇化试剂，命名为DMTP。这种新型试剂可以通过市售的 3-硫代丙酸甲酯和 CD 3 I 的简单组合来高效生产。这种新型 SCD 3试剂与烷基碘、苄基氯、芳基卤 (I, Br) 等亲电试剂表现出优异的反应活性和芳基三氟甲磺酸酯，导致氘含量高（99% D）。代表性的氘化甲硫基生物分子，例如磺胺氟草胺，已被合成用于药物发现和开发。