甲基-¹³C苯基硫醚 | 91597-65-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 甲基-¹³C苯基硫醚
• 英文名称: [¹³C]methyl phenyl sulfide
• 英文别名: [13C]methyl phenyl sulfide；13C-methyl phenyl sulfide；thioanisole-α-13C；[1-(13)C]methyl phenyl sulfide；[1-13C]methyl phenyl sulfide；[13C]-methyl phenyl sulfide；(113C)methylsulfanylbenzene
• CAS: 91597-65-8
• 化学式: C₇H₈S
• 分子量: 125.196
• InChiKey: HNKJADCVZUBCPG-OUBTZVSYSA-N

物化性质

• 沸点：
  188 °C (lit.)
• 密度：
  1.065 g/mL at 25 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  甲基-¹³C苯基硫醚 在 N-氯代丁二酰亚胺 作用下， 以 苯 为溶剂， 反应 20.0h， 以97%的产率得到(13C)chloromethyl phenyl sulfide
  参考文献：
  名称：

  Design, synthesis, and in vitro inhibitory activity toward human leukocyte elastase, cathepsin G, and proteinase 3 of saccharin-derived sulfones and congeners

  摘要：

  The inhibitory activity toward human leukocyte elastase (HLE), cathepsin G (Cat G), and proteinase 3 (PR 3) of a series of saccharin derivatives having a sulfinate leaving group was investigated. The results of this study revealed that (a) inhibitory activity is dependent on the nature and pK(a) of the leaving group, and (b) the synthesized saccharin derivatives exhibit selective inhibition toward HLE and PR 3, with low or no activity toward cathepsin G. The results of exploratory biochemical, HPLC and high-field C-13 NMR studies are also described. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00133-2
• 作为产物：
  描述：

  碘甲烷-13C 、 苯硫酚 在 sodium hydroxide 作用下， 以 水 、 苯 为溶剂， 以95.6%的产率得到甲基-¹³C苯基硫醚
  参考文献：
  名称：

  [13C]甲醇一步法大规模制备[13C]甲基苯硫醚

  摘要：

  我们开发了一种大规模的“一锅法”程序，用于将市售的 [13C]- 或 [2H3,13C] 甲醇转化为 [13C]- 或 [2H3,13C] 甲基苯硫醚。[13C] 甲基苯硫醚是一种潜在的多功能、化学稳定且非挥发性的标记前体。此外，我们报道了一种将 [13C] 甲基苯硫醚氧化为 [13C] 甲基苯砜的有效方法。最后，我们使用 [13C] 甲基苯硫醚来生产 13C 标记的甲基碘，其中正好包含一两个氘核。

  DOI：

  10.1021/op025530p

文献信息

• SINGLE CARBON PRECURSOR SYNTHONS
  申请人：Martinez Rodolfo A.

  公开号：US20080255370A1

  公开（公告）日：2008-10-16

  The chemistry of [ 13 C]methyl phenyl sulfide is exploited to produce new isotopically labeled precursors that allow for the facile assembly of a wide range of labeled molecules from simple and relatively inexpensive starting materials. These compounds are applicable to a variety of research areas such as quantum computing, metabolism and materials science.

  [13 C]甲基苯基硫化物的化学性质被利用来生产新的同位素标记前体，这些前体允许从简单且相对便宜的起始材料轻松组装出各种标记分子。这些化合物适用于诸如量子计算、代谢和材料科学等多种研究领域。
• SYNTHESIS OF PHOSPHONIC ACID LABELED COMPOUNDS
  申请人：Martinez Rodolfo A.

  公开号：US20090259064A1

  公开（公告）日：2009-10-15

  High purity isotopically labeled phosphonic acid esters can be obtained from isotopically enriched Chloro[ 13 C]methyl phenyl sulfide The labeled phosphonic acid esters can then be used as precursors for the one step production of labeled vinyl sulfides, labeled vinyl sulfoxides, and labeled vinyl sulfones. The labeled phosphonic acid esters can also be reacted with a variety of aldehydes to produce extended vinyl systems that are isotopically labeled.

  高纯度同位素标记的膦酸酯可以从同位素富集的氯代[13C]甲基苯硫醚中获得。然后，这些标记的膦酸酯可以用作制备标记的乙烯硫醚、标记的乙烯亚砜和标记的乙烯砜的一步生产的前体。这些标记的膦酸酯也可以与各种醛反应，以产生同位素标记的扩展乙烯系统。
• Large-scale preparation of¹³C-labeled 2-(phenylthio)acetic acid and the corresponding labeled sulfoxides and sulfones
  作者：Rodolfo A. Martinez、David R. Glass、Erick G. Ortiz、Marc A. Alvarez、Ernesto Juarez、Siegfried N. Lodwig、Clifford J. Unkefer

  DOI：10.1002/jlcr.2991

  日期：2013.2

  We have developed large-scale efficient procedures for the conversion of commercially available [13C]- or [2H3,13C]methanol and 13CO2 or 13C-labeled bromoacetic acid to 2-(phenylthio)[1,2-13C2]-, [1-13C]-, and [2-13C]acetic acid. The resulting derivatives are versatile, chemically stable, and nonvolatile two-carbon labeling precursors. We have used the 13C-isotopomers of 2-(phenylthio)acetic acid in the synthesis of 13C-labeled acrylic acid, methacrylic acid, and trans-crotonic acid.

  我们开发了大规模高效程序，将市售的[13C]-或[2H3,13C]甲醇和 13CO2 或 13C 标记的溴乙酸转化为 2-(苯硫基)[1,2-13C2]-、[1-13C]- 和 [2-13C]乙酸。由此得到的衍生物是用途广泛、化学性质稳定且不挥发的双碳标记前体。我们利用 2-（苯硫基）乙酸的 13C 异构体合成了 13C 标记的丙烯酸、甲基丙烯酸和反式巴豆酸。
• Synthesis of labeled oxalic acid derivatives
  申请人：The Regents of the University of California

  公开号：US06753446B1

  公开（公告）日：2004-06-22

  The present invention is directed to labeled compounds, specifically where each C* is selected from the group consisting of a carbon-12, i.e., 12C, or a carbon-13, i.e., 13C and at least one C* is 13C, R1 is selected from the group of C1-C4 lower alkyl and aryl, and X is selected from the group of —NR2R3 where R2 and R3 are each independently selected from the group of C1-C4 lower alkyl, alkoxy and aryl, —SR4 where R4 is selected from the group of C1-C4 lower alkyl, alkoxy and aryl, and —OR5 where R5 is selected from the group of C1-C4 lower alkyl, alkoxy and aryl with the proviso that when R1 is methyl then R5 is other than methyl, when R1 is ethyl then R5 is other than ethyl, and when R1 is benzyl then R5 is other than benzyl.

  本发明涉及标记化合物，具体地说，其中每个C*选自群组，该群组由碳-12，即12C，或碳-13，即13C，至少有一个C*是13C，R1选自C1-C4低烷基和芳基群组，X选自—NR2R3群组，其中R2和R3分别独立选自C1-C4低烷基、烷氧基和芳基群组，—SR4群组，其中R4选自C1-C4低烷基、烷氧基和芳基群组，以及—OR5群组，其中R5选自C1-C4低烷基、烷氧基和芳基群组，但有一个条件，即当R1为甲基时，R5不是甲基，当R1为乙基时，R5不是乙基，当R1为苄基时，R5不是苄基。
• Synthesis of [13C] and [2H] susbstituted methacrylic acid, [13C] and [2H] substituted methyl methacrylate and/or related compounds
  申请人：Alvarez A. Marc

  公开号：US20070106085A1

  公开（公告）日：2007-05-10

  The present invention is directed to labeled compounds of the formulae wherein Q is selected from the group consisting of —S—, —S(═O)—, and —S(═O) 2 —, Z is selected from the group consisting of 1-naphthyl, substituted 1-naphthyl, 2-naphthyl, substituted 2-naphthyl, and phenyl groups with the structure wherein R 1 , R 2 , R 3 , R 4 and R 5 are each independently selected from the group consisting of hydrogen, a C 1 -C 4 lower alkyl, a halogen, and an amino group selected from the group consisting of NH 2 , NHR and NRR′ where R and R′ are each independently selected from the group consisting of a C 1 -C 4 lower alkyl, an aryl, and an alkoxy group, and X is selected from the group consisting of hydrogen, a C 1 -C 4 lower alkyl group, and a fully-deuterated C 1 -C 4 lower alkyl group. The present invention is also directed to a process of preparing labeled compounds, e.g., process of preparing [ 13 C]methacrylic acid by reacting a (CH 3 CH 2 O— 13 C(O)— 13 CH 2 )— aryl sulfone precursor with 13 CHI to form a (CH 3 CH 2 O— 13 C(O)— 13 C( 13 CH 3 ) 2 )— aryl sulfone intermediate, and, reacting the (CH 3 CH 2 O— 13 C(O)— 13 C( 13 CH 3 ) 2 )— aryl sulfone intermediate with sodium hydroxide, followed by acid to form [ 13 C]methacrylic acid. The present invention is further directed to a process of preparing [ 2 H 8 ]methyl methacrylate by reacting a (HOOC—C(C 2 H 3 ) 2 — aryl sulfinyl intermediate with CD 3 I to form a ( 2 H 3 COOC—C(C 2 H 3 ) 2 )— aryl sulfinyl intermediate, and heating the( 2 H 3 COOC—C(C 2 H 3 ) 2 )— aryl sulfinyl intermediate at temperatures and for time sufficient to form [ 2 H 8 ]methyl methacrylate.

  本发明涉及公式的标记化合物，其中Q从所述组中选择，所述组由—S—、—S(═O)—和—S(═O)2—组成，Z从所述组中选择，所述组由1-萘基、取代的1-萘基、2-萘基、取代的2-萘基和苯基与结构的取代物组成，其中R1、R2、R3、R4和R5各自独立地从氢、C1-C4低烷基、卤素和NH2、NHR和NRR'组成的氨基团中选择，其中R和R'各自独立地从C1-C4低烷基、芳基和烷氧基组成的组中选择，X从氢、C1-C4低烷基和全氘代C1-C4低烷基组成的组中选择。本发明还涉及制备标记化合物的方法，例如通过将(CH3CH2O—13C(O)—13CH2)—芳基砜前体与13CHI反应以形成(CH3CH2O—13C(O)—13C(13CH3)2)—芳基砜中间体，并且通过将(CH3CH2O—13C(O)—13C(13CH3)2)—芳基砜中间体与氢氧化钠反应，随后酸化以形成[13C]丙烯酸的制备过程。本发明还涉及制备[2H8]甲基丙烯酸甲酯的方法，通过将(HOOC—C(C2H3)2—芳基亚砜中间体与CD3I反应以形成(2H3COOC—C(C2H3)2)—芳基亚砜中间体，并且在足够温度和时间下加热(2H3COOC—C(C2H3)2)—芳基亚砜中间体以形成[2H8]甲基丙烯酸甲酯。