3-methyl-2-trimethylstannyl-thiophene | 133787-28-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 金属芳基
• 英文名称: 3-methyl-2-trimethylstannyl-thiophene
• 英文别名: 3-methyl-2-trimethylstannylthiophene；Trimethyl-(3-methylthiophen-2-yl)stannane
• CAS: 133787-28-7
• 化学式: C₈H₁₄SSn
• 分子量: 260.975
• InChiKey: CHOLCHSPSGWAIG-UHFFFAOYSA-N

物化性质

• 沸点：
  110-111 °C(Press: 13 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methyl-2-trimethylstannyl-thiophene 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3-methyl-2-thiophenyl lithium
  参考文献：
  名称：

  Solution Structure and Chelation Properties of 2-Thienyllithium Reagents

  摘要：

  The solution and chelation properties of 2-thienyllithium reagents with potential amine and ether chelating groups in the 3-position and related model systems have been investigated using low temperature Li-6, Li-7, C-13, and P-31 NMR spectroscopy, N-15-labeling, and the effect of solvent additives. In THF-ether mixtures at low temperature 3-(N,N-dimethylaminomethyl)-2-thienyllithium (4) is ca. 99% dimer (which is chelated) and 1% monomer (unchelated), whereas 3-(methoxymethyl)-2thienyllithium (5) is < 10% dimer. Compound 5 crystallizes as a THF-solvated dimer, but there is no indication that the ether side chain is chelated in solution. Both 4 and 5 form PMDTA-complexed monomers almost stoichiometrically, similar to the model compound 2, in sharp contrast to phenyl analogues, which show very different behavior. The barriers to dimer interconversion are ca. 2 kcal/mol lower and chelation is significantly weaker in the 2-thienyllithium reagents than in their phenyl analogues.

  DOI：

  10.1021/jo050592+
• 作为产物：
  描述：

  三甲基氯化锡 、 2-溴-3-甲基噻吩 以68%的产率得到
  参考文献：
  名称：

  PETERS, DAN;HORNFELDT, ANNA-BRITTA;GRONOWITZ, SALO;JOHANSSON, NILS GUNNAR, J. HETEROCYCL. CHEM., 28,(1991) N, C. 529-531

  摘要：

  DOI：

文献信息

• Synthesis of various 5-substituted 2′-deoxy-3′-5′-di-<i>O</i>-acetyluridines
  作者：Dan Peters、Anna-Britta Hörnfeldt、Salo Gronowitz、Nils Gunnar Johansson

  DOI：10.1002/jhet.5570280262

  日期：1991.2

  The Pd(0)-catalyzed coupling reaction of β-5-iodo-2′-deoxy-3′,5′-di-O-acetyluridine with various heteroaryltrimethylstannyl compounds gave the corresponding β-5-heteroaryl-2′-deoxy-3′,5′-di-O-acetyluridines in moderate yields. This direct coupling approach for nucleosides represented an interesting alternative to the 5-heteroaryl functionalization of pyrimidines followed by the Hilbert-Johnson glycosylation

  Pd（0）催化的β-5-碘-2'-脱氧-3'，5'-二-O-乙酰尿苷与各种杂芳基三甲基锡烷基化合物的偶联反应得到相应的β-5-杂芳基-2'-脱氧- 3'，5'-二-O-乙酰尿苷，产率中等。这种直接连接核苷的方法代表了一个有趣的替代方法，可替代嘧啶的5-杂芳基官能化，然后进行希尔伯特-约翰逊糖基化反应，该反应通常会产生α和β端基异构体的混合物。
• PETERS, DAN;HORNFELDT, ANNA-BRITTA;GRONOWITZ, SALO;JOHANSSON, NILS GUNNAR, J. HETEROCYCL. CHEM., 28,(1991) N, C. 529-531
  作者：PETERS, DAN、HORNFELDT, ANNA-BRITTA、GRONOWITZ, SALO、JOHANSSON, NILS GUNNAR

  DOI：——

  日期：——
• Solution Structure and Chelation Properties of 2-Thienyllithium Reagents
  作者：Kevin L. Jantzi、Craig L. Puckett、Ilia A. Guzei、Hans J. Reich

  DOI：10.1021/jo050592+

  日期：2005.9.1

  The solution and chelation properties of 2-thienyllithium reagents with potential amine and ether chelating groups in the 3-position and related model systems have been investigated using low temperature Li-6, Li-7, C-13, and P-31 NMR spectroscopy, N-15-labeling, and the effect of solvent additives. In THF-ether mixtures at low temperature 3-(N,N-dimethylaminomethyl)-2-thienyllithium (4) is ca. 99% dimer (which is chelated) and 1% monomer (unchelated), whereas 3-(methoxymethyl)-2thienyllithium (5) is < 10% dimer. Compound 5 crystallizes as a THF-solvated dimer, but there is no indication that the ether side chain is chelated in solution. Both 4 and 5 form PMDTA-complexed monomers almost stoichiometrically, similar to the model compound 2, in sharp contrast to phenyl analogues, which show very different behavior. The barriers to dimer interconversion are ca. 2 kcal/mol lower and chelation is significantly weaker in the 2-thienyllithium reagents than in their phenyl analogues.