二硫化碳-14C | 63262-76-0

• 分子结构分类: 有机化合物 - 有机硫化合物
• 中文名称: 二硫化碳-14C
• 英文名称: [14C]carbon disulfide
• 英文别名: [¹⁴C]carbon disulfide；¹⁴C-Schwefelkohlenstoff；Carbon disulfide, [14C]
• CAS: 63262-76-0
• 化学式: CS₂
• 分子量: 78.132
• InChiKey: QGJOPFRUJISHPQ-NJFSPNSNSA-N

物化性质

• 闪点：
  -30 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  3
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  F,T,R
• 危险品运输编号：
  UN 2910 7

反应信息

• 作为反应物：
  描述：

  二硫化碳-14C 、 苯肼 以 乙醚 为溶剂， 反应 0.5h， 生成 [thiocarbonyl-14C]-β-phenyldithiocarbazic acid phenylhydrazine salt
  参考文献：
  名称：

  Dithizone-14C labelling and characterization

  摘要：

  制备了[硫代羰基-14C] 二硫酮，并对其进行了光谱表征。Copyright © 2003 John Wiley & Sons, Ltd. All Rights Reserved.

  DOI：

  10.1002/jlcr.778

文献信息

• Carbon-14 labeling of a trifluoromethoxy group: synthesis of a substance P antagonist
  作者：Conrad E. Raab、Dennis C. Dean、David G. Melillo

  DOI：10.1002/jlcr.502

  日期：2001.10.30

  Synthesis of a carbon-14 labeled trifluoromethoxy group has been accomplished using the stepwise oxidative fluorination–desulfurization of a readily prepared [14C]xanthate (5). This novel labeling procedure allowed a rapid synthesis of substance P antagonist candidate 1 that avoided potentially more complex ring-labeling procedures. Similar procedures have been used to prepare C-14 labeled trifluoromethyl and trifluoromethylamine groups. Copyright © 2001 John Wiley & Sons, Ltd.

  通过对容易制备的[14C]黄原酸盐（5）进行逐步氧化氟化-脱硫，合成了碳-14 标记的三氟甲氧基。这种新颖的标记程序可以快速合成候选的 P 物质拮抗剂 1，避免了可能更为复杂的环标记程序。类似的程序也被用于制备 C-14 标记的三氟甲基和三氟甲胺基团。Copyright © 2001 John Wiley & Sons, Ltd. All Rights Reserved.
• Synthesis and characterization of [Cr(CO)₅{SCHCHC(SEt)₂}] and [Cr(CO)₅{SC(SCHCH₂)SEt}] by ring-opening of 1,3-dithiolane-2-thione: crystal and molecular structure of [Cr(CO)₅{SCHCHC(SEt)₂}]
  作者：Gert J. Kruger、Lorna Linford、Helgard G. Raubenheimer

  DOI：10.1039/dt9840002337

  日期：——

  The compound [Cr(CO)5S[graphic omitted]}] reacted with Li(NPri2), CS2, and [Et3O][BF4] to afford either [Cr(CO)5SCHCHC(SEt)2}](1) or [Cr(CO)5SC(SCHCH2)SEt}](2) depending upon the reaction conditions employed. The crystal structure of the co-ordinated thioaldehyde (1) was determined [orthorhombic, space group Pbcm, a= 11.530(5), b= 18.745(9), c= 7.889(4)Å, and Z= 4] and refined to R= 0.040 and R′=

  化合物[Cr（CO）5 S [未显示图形]}]与Li（NPr i 2），CS 2和[Et 3 O] [BF 4 ]反应，制得[Cr（CO）5 S CHCH C（SEt）2 }]（1）或[Cr（CO）5 SC （SCH CH 2）SEt}]（2）取决于所采用的反应条件。确定了配位的硫醛（1）的晶体结构[斜方晶，空间群Pbcm，a = 11.530（5），b = 18.745（9），c = 7.889（4）Å，Z = 4]，并进行了精制到R＝ 0.040且R ′＝ 0.038。除了四个轴向CO配体的原子和一些氢以外，所有原子都位于一个平面上。
• Carbon 14 and stable isotope synthesis of two potent and selective phosphodiesterase type 4 inhibitors
  作者：Bachir Latli、Matt J. Hrapchak、Thomas G. Tampone、Rogelio P. Frutos、Heewon Lee

  DOI：10.1002/jlcr.4054

  日期：2023.9

  (R)‐2‐(4‐(Benzo[d]oxazol‐2‐yl)piperazin‐1‐yl)‐4‐((tetrahydro‐2H‐pyran‐4‐yl)amino)‐6,7‐dihydrothieno[3,2‐d]pyrimidine 5‐oxide (1) and (R)‐2‐(4‐(4‐chlorophenoxy)piperidin‐1‐yl)‐4‐((tetrahydro‐2H‐pyran‐4‐yl)amino)‐6,7‐dihydrothieno[3,2‐d]pyrimidine 5‐oxide (2) are two potent and selective inhibitors of phosphodiesterase type 4 (PDE4). In this manuscript, we report the detailed synthesis of these two compounds labeled with carbon 14 and with stable isotopes. The core (R)‐4‐((tetrahydro‐2H‐pyran‐4‐yl)amino)‐6,7‐dihydrothieno[3,2‐d]pyrimidine 5‐oxide is common in both inhibitors. In the radioactive synthesis, the carbon 14 atom was introduced in the benzoxazole moiety using [¹⁴C]carbon disulfide to obtain [¹⁴C]‐1 in five steps at a 55% overall yield. [¹⁴C]Urea was used to incorporate the carbon 14 atom in two steps in the dihydrothieno[3,2‐d]pyrimidine intermediate, which was then transformed in four more steps to [¹⁴C]‐2 at a 30% overall yield. Both compounds were isolated with specific activities higher than 54 mCi/mmol, radio‐ and chemical‐purities higher than 99%, and with excellent enantiomeric excess. In the stable isotope synthesis, [²H₈]piperazine was used to prepare [²H₈]‐1 in three steps in 72% overall yield, while [¹³C₆]phenol was used to prepare [¹³C₆]‐2 in four steps in 18% overall yield.

  (R)-2-(4-(苯并[d]恶唑-2-基)哌嗪-1-基)-4-((四氢-2H-吡喃-4-基)氨基)-6,7-二氢噻吩并[3、(1)和(R)-2-(4-(4-氯苯氧基)哌啶-1-基)-4-((四氢-2H-吡喃-4-基)氨基)-6,7-二氢噻吩并[3,2-d]嘧啶 5-氧化物(2)是两种强效的 4 型磷酸二酯酶 (PDE4) 选择性抑制剂。）在本手稿中，我们报告了这两种用碳 14 和稳定同位素标记的化合物的详细合成过程。(R)-4-((tetrahydro-2H-pyran-4-yl)amino)-6,7-dihydrothieno[3,2-d]pyrimidine 5-oxide 是这两种抑制剂的共同核心。在放射性合成中，使用[14C]二硫化碳在苯并恶唑分子中引入碳 14 原子，通过五个步骤得到[14C]-1，总收率为 55%。用[14C]脲分两步在二氢噻吩并[3,2-d]嘧啶中间体中加入碳 14 原子，然后再分四步转化为[14C]-2，总收率为 30%。分离出的这两种化合物的比活度均高于 54 mCi/mmol，放射性和化学纯度均高于 99%，对映体过量性极佳。在稳定同位素合成中，用[2H8]哌嗪分三步制备了[2H8]-1，总收率为 72%，而用[13C6]苯酚分四步制备了[13C6]-2，总收率为 18%。
• CROWE, A. M.;IFE, R. J.;MITCHELL, M. B.;SAUNDERS, D., J. LABELLED COMPOUNDS AND RADIOPHARM., 1986, 23, N 1, 21-33
  作者：CROWE, A. M.、IFE, R. J.、MITCHELL, M. B.、SAUNDERS, D.

  DOI：——

  日期：——
• TANAKA A.; FUKUOKA M.; ADACHI T.; YAMAHA T., J. LABELLED COMPOUNDS AND RADIOPHARM., 23,(1986) N 4, 405-413
  作者：TANAKA A.、 FUKUOKA M.、 ADACHI T.、 YAMAHA T.

  DOI：——

  日期：——