| 1228385-73-6

• CAS: 1228385-73-6
• 化学式: C₁₀H₈BrFeI
• 分子量: 390.829
• InChiKey: JAIWDFOQGWDUBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  、 三甲基乙炔基硅 在 copper(l) iodide 、 二(三叔丁基膦)钯 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以91%的产率得到((3-bromoferrocenyl)ethynyl)trimethylsilane
  参考文献：
  名称：

  二取代的二茂铁基碘和硫属炔烃作为手性卤素和硫属元素键的供体

  摘要：

  基于卤素和硫族元素键（XB和ChB）的不对称催化仍处于起步阶段，寻找新的手性XB和ChB供体代表了其发展的关键一步。在这种情况下，我们设计并准备了包含三个关键子结构的新基序：即，以碘和硫属元素原子为中心的电子电荷密度耗尽区域，乙炔基官能度和平面手性二茂铁基平台。通过不对称合成将九个二茂铁基碘炔烃制备为纯对映体。外消旋二茂铁基碘炔的XB供体性质在溶液中通过两个基准反应得到证明：Ritter反应和硫代酰胺合成苯并恶唑。相反，二茂铁基硫属炔烃在这些反应中活性低得多。

  DOI：

  10.1021/acs.organomet.0c00633
• 作为产物：
  描述：

  溴代二茂铁 、 碘 在 (2,2,6,6-tetramethylpiperidino)2Zn 、 (2,2,6,6-tetramethylpiperidinato)Li 作用下， 以 tetrahydrofuran 为溶剂， 以64%的产率得到2-bromo-1-iodoferrocene
  参考文献：
  名称：

  Deprotonative metallation of ferrocenes using mixed lithium–zinc and lithium–cadmium combinations

  摘要：

  一种混合锂-镉酰胺与锂和锌酰胺的组合与一系列二茂铁进行反应；通常在室温下，通过随后用碘淬灭可以证明，发生了选择性的去质子化单金属化或双金属化反应。

  DOI：

  10.1039/b924939g

文献信息

• Halide-Mediated<i>Ortho</i>-Deprotonation Reactions Applied to the Synthesis of 1,2- and 1,3-Disubstituted Ferrocene Derivatives
  作者：Afrooz Zirakzadeh、Alexander Herlein、Manuela A. Groß、Kurt Mereiter、Yaping Wang、Walter Weissensteiner

  DOI：10.1021/acs.organomet.5b00464

  日期：2015.8.10

  The ortho-deprotonation of halide-substituted ferrocenes by treatment with lithium tetramethylpiperidide (LiTMP) has been investigated. Iodo-, bromo-, and chloro-substituted ferrocenes were easily deprotonated adjacent to the halide substituents. The synthetic applicability of this reaction was, however, limited by the fact that, depending on the temperature and the degree of halide substitution, scrambling of both iodo and bromo substituents at the ferrocene core took place. Iodoferrocenes could not be transformed selectively into ortho-substituted iodoferrocenes since, in the presence of LiTMP, the iodo substituents scrambled efficiently even at -78 degrees C, and this process had occurred before electrophiles had been added. Bromoferrocene and certain monobromo-substituted derivatives, however, could be efficiently ortho-deprotonated at low temperature and reacted with a number of electrophiles to afford 1,2- and 1,2,3-substituted ferrocene derivatives. For example, 2-bromo-1-iodoferrocene was synthesized by ortho-deprotonation of bromoferrocene and reaction with the electrophiles diiodoethane and diiodotetrafluoroethane, respectively. In this and related cases the iodide scrambling process and further product deprotonation due to the excess LiTMP could be suppressed efficiently by running the reaction at low temperature and in inverse mode. In contrast to the low-temperature process, at room temperature bromo substituents in bromoferrocenes scrambled in the presence of LiTMP. Chloro- and 1,2-dichloroferrocene could be ortho-deprotonated selectively, but in neither case was scrambling of a chloro substituent observed. As a further application of this ortho-deprotonation reaction, a route for the synthesis of 1,3-disubstituted ferrocenes was developed. 1,3-Diiodoferrocene was accessible from bromoferrocene in four steps. On a multigram scale an overall yield of 41% was achieved. 1,3-Diiodoferrocene was further transformed into symmetrically 1,3-disubstituted ferrocenes (1,3-R(2)Fc; R = CHO, COOEt, CN, CH=CH2).