3-(bromomethyl)-2-iodothiophene | 902147-10-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 3-(bromomethyl)-2-iodothiophene
• 英文别名: 3-bromomethyl-2-iodothiophene；3-(Bromomethyl)-2-iodothiophene
• CAS: 902147-10-8
• 化学式: C₅H₄BrIS
• 分子量: 302.961
• InChiKey: MRMFWMJEQJZRGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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-(bromomethyl)-2-iodothiophene 在 氢氧化钾 、 叔丁基锂 作用下， 以 四氢呋喃 、 二甲基亚砜 、 正戊烷 为溶剂， 反应 10.0h， 生成 N,N-diethyl-1-(thiophen-3-ylmethyl)pyrrole-2-carboxamide
  参考文献：
  名称：

  Intramolecular cyclisation of functionalised heteroaryllithiums. Synthesis of novel indolizinone-based compounds

  摘要：

  The intramolecular cyclisation of heteroaryllithiums derived from N-heteroarylmethylpyrrole-2-carboxam ides takes place smoothly at low temperature when N-methoxy-N-methyl and morpholine amides are used as internal electrophiles. Halogen-lithium exchange using n-BuLi is the method of choice to achieve metalation on the quinoline and pyridine derivatives, while directed lithiation (LDA) works better for furan. In the case of thiophene both methodologies can be applied. These metalation-cyclisation sequences provide a useful entry to several types of indolizidine based compounds (pyrrolo[1,2-b]acridinones, pyrrolo[1,2-g]quinolones, thieno and furo[3,2-f]indolizinones). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.057
• 作为产物：
  描述：

  3-噻吩甲醇 在 碘 、 silver trifluoroacetate 、 三溴化磷 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 16.5h， 生成 3-(bromomethyl)-2-iodothiophene
  参考文献：
  名称：

  Intramolecular cyclisation of functionalised heteroaryllithiums. Synthesis of novel indolizinone-based compounds

  摘要：

  The intramolecular cyclisation of heteroaryllithiums derived from N-heteroarylmethylpyrrole-2-carboxam ides takes place smoothly at low temperature when N-methoxy-N-methyl and morpholine amides are used as internal electrophiles. Halogen-lithium exchange using n-BuLi is the method of choice to achieve metalation on the quinoline and pyridine derivatives, while directed lithiation (LDA) works better for furan. In the case of thiophene both methodologies can be applied. These metalation-cyclisation sequences provide a useful entry to several types of indolizidine based compounds (pyrrolo[1,2-b]acridinones, pyrrolo[1,2-g]quinolones, thieno and furo[3,2-f]indolizinones). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.057

文献信息

• Enantioselective Palladium-Catalyzed Heck-Heck Cascade Reactions: Ready Access to the Tetracyclic Core of Lycorane Alkaloids
  作者：Estibaliz Coya、Nuria Sotomayor、Esther Lete

  DOI：10.1002/adsc.201500431

  日期：2015.10.12

  A rapid and efficient access to a wide variety of enantiomerically enriched C-11b substituted lycorane analogues can be achieved via a catalytic asymmetric Heck–Heck 6-exo/6-endo cascade reaction in the presence of (R)-BINAP.

  在（R）-BINAP存在下，可通过催化不对称的Heck-Heck 6- exo / 6-内消旋级联反应，快速有效地获得各种对映体富集的C-11b取代的二十烷基类似物。
• Intramolecular Direct Arylation and Heck Reactions in the Formation of Medium-Sized Rings: Selective Synthesis of Fused Indolizine, Pyrroloazepine and Pyrroloazocine Systems
  作者：Estibaliz Coya、Nuria Sotomayor、Esther Lete

  DOI：10.1002/adsc.201400075

  日期：2014.5.26

  The intramolecular palladium‐catalyzed reaction of N‐(iodoarylalkyl)pyrroles can be applied for the selective synthesis of medium‐sized rings by choosing the appropriate catalytic systems to direct the reaction to the alkene or to the pyrrole nucleus. These reactions can also be extended to the corresponding heteroaryl halides. Thus, reaction conditions have been established to access selectively to

  N-（碘代芳基烷基）吡咯的分子内钯催化反应可通过选择合适的催化体系，将反应导向烯烃或吡咯核，用于中型环的选择性合成。这些反应也可以扩展至相应的杂芳基卤化物。因此，已经建立了反应条件以选择性地进入（杂）融合的吲哚嗪，吡咯并氮杂和吡咯并偶氮嗪系统。
• Intramolecular cyclisation of functionalised heteroaryllithiums. Synthesis of novel indolizinone-based compounds
  作者：Javier Ruiz、Esther Lete、Nuria Sotomayor

  DOI：10.1016/j.tet.2006.04.057

  日期：2006.6

  The intramolecular cyclisation of heteroaryllithiums derived from N-heteroarylmethylpyrrole-2-carboxam ides takes place smoothly at low temperature when N-methoxy-N-methyl and morpholine amides are used as internal electrophiles. Halogen-lithium exchange using n-BuLi is the method of choice to achieve metalation on the quinoline and pyridine derivatives, while directed lithiation (LDA) works better for furan. In the case of thiophene both methodologies can be applied. These metalation-cyclisation sequences provide a useful entry to several types of indolizidine based compounds (pyrrolo[1,2-b]acridinones, pyrrolo[1,2-g]quinolones, thieno and furo[3,2-f]indolizinones). (c) 2006 Elsevier Ltd. All rights reserved.