3,4-二氢-4-碘甲基-2H-1-苯并吡喃 | 107616-56-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 3,4-二氢-4-碘甲基-2H-1-苯并吡喃
• 英文名称: 3-(iodomethyl)chromane
• 英文别名: 4-(iodomethyl)chroman；4-iodomethylchroman；3,4-Dihydro-4-(iodomethyl)-2h-1-benzopyran；4-(iodomethyl)-3,4-dihydro-2H-chromene
• CAS: 107616-56-8
• 化学式: C₁₀H₁₁IO
• 分子量: 274.101
• InChiKey: WUBBCYRDJZNINH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  3,4-二氢-4-碘甲基-2H-1-苯并吡喃 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以83%的产率得到4-methylenechromane
  参考文献：
  名称：

  烯烃的分子内芳基化反应：一种灵活的方法来处理色曼和四氢喹啉衍生物

  摘要：

  描述了一种通过不同烯丙基苯基醚与 Ipy2BF4 反应制备色满衍生物的无金属方法。通过起始材料的直接环化，可以顺利地获得该框架。此外，还可以完成包括初始重排和进一步环化在内的不寻常的选择性序列，温度是一个极好的控制因素。当使用烯丙胺时，该过程可以扩展到四氢喹啉的合成。此外，还设计了两个级联反应，导致相关的含氧和含氮骨架。

  DOI：

  10.1021/ja0397299
• 作为产物：
  描述：

  (3,4-dihydro-2H-chromen-4-yl)methanol 在 咪唑 、 三苯基膦二碘化物 作用下， 以 二氯甲烷 为溶剂， 生成 3,4-二氢-4-碘甲基-2H-1-苯并吡喃
  参考文献：
  名称：

  2-Substituted (2SR)-2-Amino-2-((1SR,2SR)-2-carboxycycloprop-1-yl)glycines as Potent and Selective Antagonists of Group II Metabotropic Glutamate Receptors. 1. Effects of Alkyl, Arylalkyl, and Diarylalkyl Substitution

  摘要：

  In this paper, we describe the synthesis of a series of a-substituted analogues of the potent and selective group II metabotropic glutamate receptor (mGluR) agonist (1S,1'S,2'S)-carboxy-cyclopropylglycine (2, L-CCG 1). Incorporation of a substituent on the amino acid carbon converted the agonist 2 into antagonist. Ail of the compounds were prepared and tested as a series of four isomers, i.e., two racemic diastereomers. We explored alkyl substitution, both normal and terminally branched; phenylalkyl and diphenylalkyl substitution; and a variety of aromatic and carbocyclic surrogates for phenyl. Affinity for group II mGluRs was measured using [H-3]glutamic acid (Glu) binding in rat forebrain membranes. Antagonist activity was confirmed for these compounds by measuring their ability to antagonize (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid-induced inhibition of forskolin-stimulated cyclic-AMP in RGT cells transfected with human mGluR2 and mGluR3. We found that while alkyl substitution provided no increase in affinity relative to 2, phenylethyl and diphenylethyl substitution, as in 105 and 109, respectively, were quite beneficial, The affinity of 109 was further enhanced when the two aromatic rings were joined by an oxygen or sulfur atom to form the tricyclic xanthylmethyl and thioxanthylmethyl amino acids 113 and 114, respectively. Amino acid 113, with an IC50 of 0.10 mu M in the [H-3]Glu binding assay, was 52-fold more patent than 2, whose IC50 was 0.47 mu M.

  DOI：

  10.1021/jm970497w

文献信息

• Photo-induced Carboiodination: A Simple Way to Synthesize Functionalized Dihydrobenzofurans and Indolines
  作者：Xiaobo Yang、Wenbo Liu、Lu Li、Wei Wei、Chao-Jun Li

  DOI：10.1002/chem.201603608

  日期：2016.10.17

  readily available and cheap aryl bromides and sodium iodide as the starting materials to synthesize valuable functionalized dihydrobenzofurans and indolines in good to excellent yields with broad functional‐group compatibility. As examples to demonstrate the utility of this protocol, gram‐scale reactions and further transformations of the products were accomplished towards the synthesis of bioactive

  在此，我们报告了在非常温和的条件下发生的简单的氧化还原中性和pH中性光诱导的碳碘化反应。该方案采用容易获得且便宜的芳基溴化物和碘化钠作为起始原料，以良好的产率和优异的产率以及广泛的官能团相容性来合成有价值的官能化二氢苯并呋喃和二氢吲哚。作为证明该方案实用性的实例，完成了克级反应和产物的进一步转化，以合成生物活性药物候选物。最重要的是，据我们所知，该反应是级联原子-自由基转移加成反应的第一个例子，涉及芳族C-Br键的裂解。
• Cyclizing Radical Carboiodination, Carbotelluration, and Carboaminoxylation of Aryl Amines
  作者：Marcel Hartmann、Armido Studer

  DOI：10.1002/anie.201403968

  日期：2014.7.28

  Radical carboiodination of various aryl amines is reported. Aryl diazonium salts, generated in situ from the corresponding aryl amines, are reacted with Bu4NI to provide the corresponding aryl radicals which undergo 5‐exo or 6‐exo cyclization. Iodine abstraction eventually affords the carboiodinated products in good to excellent yields. If TEMPO is added, the cascade provides the cyclized carboaminoxylation

  报道了各种芳基胺的自由基碳碘化。由相应的芳基胺原位生成的芳基重氮盐与Bu 4 NI反应生成相应的芳基，这些芳基经过5-exo或6-exo环化。碘的提取最终以良好或优异的收率提供了碳碘化产品。如果添加TEMPO，则级联反应会提供环化的氨基碳酰化产物。在PhTeTePh存在下进行反应可得到苯基碲化的环化产物。
• Iododediazoniation of arenediazonium salts accompanied by aryl radical ring closure
  作者：Athelstan L. J. Beckwith、Gordon F. Meijs

  DOI：10.1021/jo00386a007

  日期：1987.5
• BECKWITH A. L. J.; MEIJS G. F., J. ORG. CHEM., 52,(1987) N 10, 1922-1930
  作者：BECKWITH A. L. J.、 MEIJS G. F.

  DOI：——

  日期：——
• Mechanistic and kinetic studies on the iododediazoniation reaction
  作者：Anil N. Abeywickrema、Athelstan L. J. Beckwith

  DOI：10.1021/jo00388a040

  日期：1987.6