2-iodo-4-(dimethylamino)benzaldehyde | 207789-57-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-iodo-4-(dimethylamino)benzaldehyde
• 英文别名: 4-(dimethylamino)-2-iodobenzaldehyde
• CAS: 207789-57-9
• 化学式: C₉H₁₀INO
• 分子量: 275.089
• InChiKey: OEUAIXNQSGERNH-UHFFFAOYSA-N

物化性质

• 沸点：
  353.4±37.0 °C(Predicted)
• 密度：
  1.706±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-iodo-4-(dimethylamino)benzaldehyde 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 吡啶 、 4-二甲氨基吡啶 、 1,4-环己二烯 、 水 、 sodium cyanoborohydride 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 6.0h， 生成 Dimethyl-[3-trimethylsilanylethynyl-4-(3-trimethylsilanyl-prop-2-ynyl)-phenyl]-amine
  参考文献：
  名称：

  Towards a New Type of Aromatic Diynes Activation: Synthesis of a Novel Bicyclic Enediyne

  摘要：

  我们合成了芳香族无环二炔 2 和 3，以测试对其环化进行新活化的可行性。此外，当芳香环是否具有分子内触发装置时，13 和 20 在 Nozaki-Kishi 环化反应中的稳定性就会出现差异。因此，芳香族双环烯二炔 14 是稳定的，而 21 尚未分离出来。

  DOI：

  10.1055/s-1998-1693
• 作为产物：
  描述：

  3-iodo-N,N-dimethylaniline 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以91 %的产率得到2-iodo-4-(dimethylamino)benzaldehyde
  参考文献：
  名称：

  一种基于取代罗丹明的可逆荧光探针，用于谷胱甘肽的体内定量

  摘要：

  通过生物成像量化细胞和生物体中的谷胱甘肽 (GSH) 是通过使用Zp SiP 实现的，Zp SiP 是一种基于取代罗丹明的比例探针，与 GSH 具有可靠的反应性。该探针成功监测了肿瘤组织、慢性肾功能衰竭和肝纤维化生物体中GSH的动态变化，揭示了相关的病理过程和机制。

  DOI：

  10.1002/anie.202217326

文献信息

• Stereoselective synthesis of a <i>Podophyllum</i> lignan core by intramolecular reductive nickel-catalysis
  作者：Jian Xiao、Xiao-Wei Cong、Gui-Zhen Yang、Ya-Wen Wang、Yu Peng

  DOI：10.1039/c8cc00001h

  日期：——

  A Ni-catalyzed reductive cascade to a diastereocontrolled construction of THN[2,3-c]furan, is developed. The mild reaction conditions led to the tolerance of broad functional groups that can be placed in almost every position of this skeleton with good yields. The conformational control for the observed trans- or cis-fused selectivity during this tandem cyclization-coupling is also proposed.

  镍催化还原还原级联的非对映体控制的THN [2,3-c]呋喃。温和的反应条件导致了宽泛的官能团的耐受性，这些官能团几乎可以以良好的产率置于该骨架的每个位置。还提出了在串联环化偶联过程中观察到的反式或顺式融合选择性的构象控制。
• In Situ Generation of 1-Propyne: A Useful Introduction of 1-Propyne on Unsaturated Halogenated Compounds through the Sonogashira Reaction
  作者：Estelle Abraham、Jean Suffert

  DOI：10.1055/s-2002-19769

  日期：——

  Reaction of (E/Z)-1-bromopropene with exactly 1.42 equivalents of nBuLi followed by addition of water produces in situ a THF solution of propyne. Addition of a vinylic or aromatic halogenated substrates, Pd(PPh3)2Cl2, CuI and an amine to this solution give high yield of the corresponding coupling product bearing a propyne moiety. This practical procedure avoids the use of expensive and inflammable propyne gas which need a special apparatus for bubbling it into the reaction flask.

  (E/Z)-1-溴丙烯与正好 1.42 个当量的 nBuLi 反应，然后加水，在原位生成丙炔的 THF 溶液。在该溶液中加入乙烯基或芳香族卤化底物、Pd(PPh3)2Cl2、CuI 和胺，可得到高产率的带有丙炔分子的相应偶联产物。这种实用的方法避免了使用昂贵且易燃的丙炔气体，因为这种气体需要一种特殊的装置将其鼓入反应烧瓶中。
• NEAR INFRARED FLUOROGEN AND FLUORESCENT ACTIVATING PROTEINS FOR IN VIVO IMAGING AND LIVE-CELL BIOSENSING
  申请人：Carnegie Mellon University

  公开号：US20140243509A1

  公开（公告）日：2014-08-28

  Tissue slices and whole organisms offer substantial challenges to fluorescence imaging. Autofluorescence and absorption via intrinsic chromophores, such as flavins, melanin, and hemoglobins, confound and degrade output from all fluorescent tags. An “optical window,” farther red than most autofluorescence sources and in a region of low hemoglobin and water absorbance, lies between 650 and 900 nm. This valley of relative optical clarity is an attractive target for fluorescence-based studies within tissues, intact organs, and living organisms. Novel fluorescent tags were developed herein, based upon a genetically targeted fluorogen activating protein and cognate fluorogenic dye that yields emission with a peak at 733 nm exclusively when complexed as a “fluoromodule”. This tool improves substantially over previously described far-red/NIR fluorescent proteins in terms of brightness, wavelength, and flexibility by leveraging the flexibility of synthetic chemistry to produce novel chromophores.

  组织切片和整个生物体对荧光成像提出了重大挑战。自发荧光和内在色素（如黄酮，黑色素和血红蛋白）的吸收会干扰和降解所有荧光标记的输出。在650到900纳米之间，比大多数自发荧光源更远的“光学窗口”处于低血红蛋白和水吸收区域内，是组织，完整器官和活体内荧光研究的有吸引力的目标。本文开发了一种新型荧光标记，基于基因定向荧光原活化蛋白和相应的荧光原染料，仅当复合为“荧光模块”时，才产生峰值为733纳米的发射。通过利用合成化学的灵活性来生产新的色素，该工具在亮度，波长和灵活性方面显着优于先前描述的远红外/近红外荧光蛋白。
• Synthesis of 4-(1-Alkenyl)isoquinolines by Palladium(II)-Catalyzed Cyclization/Olefination
  作者：Qinhua Huang、Richard C. Larock

  DOI：10.1021/jo0261303

  日期：2003.2.1

  A variety of 4-(l-alkenyl)-3-arylisoquinolines have been prepared in moderate to excellent yields by the Pd(II)-catalyzed cyclization of 2-(1-alkynyl)arylaldimines in the presence of various alkenes. The introduction of an o-methoxy group on the arylaldimine promotes the Pd-catalyzed cyclization and stabilizes the resulting Pd(II) intermediate, improving the yields of the isoquinoline products. Ketone-containing isoquinolines 36 and 49-51 have also been prepared by this process when unsaturated alcohols are employed as the alkenes.
• Synthesis of Isoquinolines and Pyridines by the Palladium-Catalyzed Iminoannulation of Internal Alkynes
  作者：Kevin R. Roesch、Haiming Zhang、Richard C. Larock

  DOI：10.1021/jo0105540

  日期：2001.11.1

  A wide variety of substituted isoquinoline, tetrahydroisoquinoline, 5,6-dihydrobenz[f]isoquinoline, pyrindine, and pyridine heterocycles have been prepared in good to excellent yields via annulation of internal acetylenes with the tert-butylimines of o-iodobenzaldehydes and 3-halo-2-alkenals in the presence of a palladium catalyst. The best results are obtained by employing 5 mol % of Pd(OAc)(2), an excess of the alkyne, 1 equiv of Na2CO3 as a base, and 10 mol % of PPh3 in DMF as the solvent. This annulation methodology is particularly effective for aryl- or alkenyl-substituted alkynes. When electron-rich imines are employed, this chemistry can be extended to alkyl-substituted alkynes. Trimethylsilyl-substituted alkynes also undergo this annulation process to afford monosubstituted heterocyclic products absent the silyl group.