3,4-diiodopyrrole | 56821-81-9

• 分子结构分类: 有机化合物 - 有机卤素化合物
• 英文名称: 3,4-diiodopyrrole
• 英文别名: 3,4-diiodo-1H-pyrrole
• CAS: 56821-81-9
• 化学式: C₄H₃I₂N
• 分子量: 318.884
• InChiKey: XDQMCAVVNFFYNC-UHFFFAOYSA-N

物化性质

• 熔点：
  40 °C(Solv: ligroine (8032-32-4))
• 沸点：
  340.6±27.0 °C(Predicted)
• 密度：
  2.849±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3,4-diiodopyrrole 、 2-(三甲基硅烷基)乙氧甲基氯 在 sodium hydride 作用下， 以80%的产率得到3,4-Diiodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole
  参考文献：
  名称：

  Heck reactions of amino acid building blocks: application to the synthesis of pyrrololine analogues

  摘要：

  Heck reactions of unsaturated amino acid building blocks are described which allow acess to homo- and bis-homophenylalanine derivatives and to gamma,delta-unsaturated amino acids. Preliminary synthetic studies utilising this chemistry for the preparation of pyrrololine and deoxypyrrololine analogues are also reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00512-9
• 作为产物：
  描述：

  1-(triisopropylsilyl)-3,4-diiodopyrrole 在 potassium phosphate 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到3,4-diiodopyrrole
  参考文献：
  名称：

  Heck reactions of amino acid building blocks: application to the synthesis of pyrrololine analogues

  摘要：

  Heck reactions of unsaturated amino acid building blocks are described which allow acess to homo- and bis-homophenylalanine derivatives and to gamma,delta-unsaturated amino acids. Preliminary synthetic studies utilising this chemistry for the preparation of pyrrololine and deoxypyrrololine analogues are also reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00512-9

文献信息

• N-(Triisopropylsilyl)pyrrole. A progenitor "par excellence" of 3-substituted pyrroles
  作者：Brian L. Bray、Peter H. Mathies、Reto Naef、Dennis R. Solas、Thomas T. Tidwell、Dean R. Artis、Joseph M. Muchowski

  DOI：10.1021/jo00313a019

  日期：1990.12

  A very effective strategy has been devised for the synthesis of 3-substituted pyrroles based on the use of the triisopropylsilyl (TIPS) moiety as a sterically demanding nitrogen substituent to obstruct the attack of electrophilic reagents at the alpha-positions. 1-(Triisopropylsilyl)pyrrole (1) undergoes highly preferential kinetic electrophilic substitution at the beta-position with a variety of electrophiles (Br+, I+, NO2+, RCO+, etc.) and fluoride ion induced desilylation of the products provides the corresponding 3-substituted pyrroles in good overall yields. Competitive trifluoroacetylation experiments demonstrate that substitution of TIPS-pyrrole at the alpha-positions is decelerated by a factor of > 10(4), vs pyrrole at the same sites, without affecting reactivity at the beta-positions. 1-(Triisopropylsilyl)-3-bromopyrrole (2) is readily converted into the 3-lithio compound 44 by bromine-lithium interchange with alkyllithium reagents. This previously unavailable, formal equivalent of 3-lithiopyrrole is itself an excellent source of a wide range of beta-substituted pyrroles, many of which would not be directly preparable from 1. TIPS-pyrrole can be 3,4-dihalogenated and these compounds undergo sequential halogen-metal interchange trapping reactions. This process is exemplified by an efficient, three-step synthesis of the antibiotic verrucarin E (63) from the dibromo compound 5.
• Octaiodoporphyrin
  作者：Ivar K. Thomassen、Hugo Vazquez-Lima、Kevin J. Gagnon、Abhik Ghosh

  DOI：10.1021/acs.inorgchem.5b02127

  日期：2015.12.7

  Interaction of 3,4-diiodopyrrole with 4-trifluoromethylbenzaldeyde under carefully optimized, Lindsey-type conditions at -10 degrees C has led to the synthesis of the first beta-octaiodoporphyrin, H-2[I(8)TpCF(3)PP]. The free ligand readily yielded Ni, Cu, and Zn complexes, which all proved amenable to single-crystal X-ray structure analyses. The zinc complex Zn[I8TpCF3PP] exhibits the most saddled porphyrin core for any simple porphyrin known to date and a dramatically red-shifted optical spectrum with a Soret maximum at 495 nm.
• BRAY, BRIAN L.;MATHIES, PETER H.;NAEF, RETO;SOLAS, DENNIS R.;TIDWELL, THO+, J. ORG. CHEM., 55,(1990) N6, C. 6317-6328
  作者：BRAY, BRIAN L.、MATHIES, PETER H.、NAEF, RETO、SOLAS, DENNIS R.、TIDWELL, THO+

  DOI：——

  日期：——
• FARNIER M.; FOURNARI P., J. HETEROCYCL. CHEM. <JHTC-AD>, 1975, 12, NO 2, 373-374
  作者：FARNIER M.、 FOURNARI P.

  DOI：——

  日期：——