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Hydroxytrimethylstannane 三甲基氢氧化锡

规格: 98%
CAS: 56-24-6
产品编号: H15248
MDL: MFCD00013929
品牌: INFI

一种温和的选择性水解试剂

酯类化合物的水解在有机合成中至关重要,但常用的水解方法存在以下问题:1)其他酯基同时水解;2)化合物的立体中心消旋化;3)发生不必要的消除反应。而三甲基氢氧化锡(Me3SnOH)作为一种温和的碱,可以实现化合物中酯基的选择性水解。

该方法首次发现是Scripps研究所K. C. Nicolaou课题组在研究硫链蛋白(一种高度复杂的硫肽抗生素)过程中,中间体敏感不能耐受普通水解条件,而Me3SnOH以高产率实现了乙酸甲酯和异丙酯的选择性水解[1]。自此他们课题组对Me3SnOH在酯水解应用中进行了深入的研究,实验结果表明,Me3SnOH在温和的进行酯基水解的同时,保护了在碱性条件下易消旋化的立体中心(如图一);除此之外底物存在甲酯、乙酯和异丙酯等多种酯基时,可以实现选择性优先水解甲酯(如图二)。

图一:(R)-4-羟基苯甘氨酸衍生物的甲酯水解

图二:选择性酯水解

以上图片均来自参考文献

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参考文献:Nicolaou, K.C., Estrada, A.A., Zak, M., Lee, S.H. and Safina, B.S. A Mild and Selective Method for the Hydrolysis of Esters with Trimethyltin Hydroxide. Angewandte Chemie International Edition, 2005, 44, 1378-1382.

Chemical NameTrimethyltinhydroxide
Synonym Hydroxytrimethylstannane Trimethylstannanol Stannane, hydroxytrimethyl- Trimethyl tin hydroxide Tin, hydroxytrimethyl- Trimethylstannyl hydroxide 三甲基氢氧化锡, 98% Hydroxytrimethyltin; Trimethylhydroxytin; Trimethylstannanol; Trimethylstannyl hydroxide Trimethyltin hydroxide Trimethylstannylhydroxid Trimethylzinnhydroxid Trimethylzinn-hydroxid Tin, trimethyl-, hydroxide Trimethylhydroxytin Hydroxytrimethyltin
MDL NumberMFCD00013929
CAS Number56-24-6
Chemical Name Translation三甲基氢氧化锡
Wiswesser Line NotationQ-SN-1&1&1
LabNetwork Molecule IDLN01301690
TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1800 ug/kg
TOXIC EFFECTS :
   Cardiac - pulse rate increase, without fall in BP
   Vascular - BP elevation not characterized in autonomic section
REFERENCE :
   JPETAB Journal of Pharmacology and Experimental Therapeutics.  (Williams &
   Wilkins Co., 428 E. Preston St., Baltimore, MD 21202)  V.1-    1909/10-
   Volume(issue)/page/year: 28,367,1926

RTECSWH8400000
Safety Statements
  • S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置;
  • S61 Avoid release to the environment. Refer to special instructions/safety data sheet 避免释放到环境中,参考特别指示/安全收据说明书;
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时,立即求医(可能时出示标签);
  • S27/28
    Packing GroupII
    UN Number UN3146
    Risk Statements
    • R26/27/28 Very toxic by inhalation, in contact with skin and if swallowed 吸入,皮肤接触及吞食都有剧毒
    • R50/53
      Storage condition Moisture Sensitive
      Restrict 剧毒
    • {uni_hamburg} Short: III/5a
    • Title: Structure Data of Organic Crystals: C ... C 13
    • Author: Schudt, E.; Weitz, G.
    • Editor: Hellwege, K.-H.; Hellwege, A.M.
    • Source: Landolt-Börnstein, New Series
    • Volume: III/5a
    • Year: 1971
    • ISBN: 3-540-05177-5
    • ISBN: 978-3-540-05177-0
    • Internet Resource: DOI:10.1007/b19970
    • RefComment: XXI, 736 pages, and VII, 890 pages. Hardcover
    • Abstract: Volume III/5 offers a compitation as complete as possible of the space groups and lattice con-stants of all crystals which have been studied by means of X-rays, neutron and electron diffraction.
    • 56-24-6 H15248 Hydroxytrimethylstannane
三甲基氢氧化锡

      化学属性

      Mol. Formula(CH3)3SnOH
      Mol. Weight181
      Melting Point114-118°
      TSCANo
      Flash Point26 ºC
      Boiling Point119 ºC
      Density1.0

      *以上化合物性质及应用等信息仅供参考