4-乙氧基-3-碘苯甲醛 | 184033-45-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-乙氧基-3-碘苯甲醛
• 英文名称: 3-iodo-4-ethoxybenzaldehyde
• 英文别名: 4-Ethoxy-3-iodobenzaldehyde
• CAS: 184033-45-2
• 化学式: C₉H₉IO₂
• mdl: MFCD02629428
• 分子量: 276.074
• InChiKey: ZMSKRAIPMCFCQI-UHFFFAOYSA-N

物化性质

• 沸点：
  336.6±32.0 °C(Predicted)
• 密度：
  1.686±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2913000090

反应信息

• 作为反应物：
  描述：

  4-乙氧基-3-碘苯甲醛 、 2-(3,4-diaminophenyl)-6-(1-methyl-4-piperazinyl)benzimidazole 在 molecular sieve 作用下， 以 硝基苯 、 甲苯 为溶剂， 反应 36.0h， 生成 2-[2-(3-iodo-3-ethoxyphenyl)-6-benzimidazolyl]-6-(1-methyl-4-piperazinyl)benzimidazole
  参考文献：
  名称：

  [¹²⁵I/¹²⁷I]IodoHoechst 33342:  Synthesis, DNA Binding, and Biodistribution

  摘要：

  An iodinated analog of the DNA-minor-groove-binding agent Hoechst 33342 has been synthesized and evaluated for DNA binding and tumor targeting. The bis-benzimidazole ring system of the title compound was constructed from the piperazinyl terminus via a Pinner-type cyclization followed by oxidative cyclization of the diamine Schiff base. To synthesize radioiodoHoechst 33342, (trimethylstannyl)Hoechst 33342 was prepared by the same strategy and subjected to mild radioiodedestannylation in the presence of lactoperoxidase. After purification by HPLC, the radiochemical was separated in carrier-free form with >85% radiochemical yield and >99% chemical and radiochemical purity. Fluorescence spectrometric analysis of the binding of iodoHoechst 33342 calf thymus DNA gave an equilibrium association constant (K-a) of 2.57 x 10(7) M(-1) comparable to the K-a value of Hoechst 33342. Fluorescence microscopy of viable V79 cells demonstrated that the iodinated dye stained the nuclei with avidity similar to that of the noniodinated dye. The biodistribution of [I-125]-iodoHoechst 33342 in LS174T tumor-bearing athymic mice 4 h postadministration showed a tumor uptake of 3-4% injected dose per gram (ID/g), tumor/blood ratio of 6-8, and tumor/nontumor ratios above unity for most organs. A low thyroid uptake (similar to 2% ID/g) indicated that the radiochemical did not deiodinate and was stable in vivo.

  DOI：

  10.1021/jm9602672
• 作为产物：
  描述：

  4-乙氧基苯甲醛 在 iron(III) chloride 、 N-碘代丁二酰亚胺 、 1-丁基-3-甲基咪唑二(三氟甲基磺酰)酰亚胺 作用下， 反应 2.0h， 以81%的产率得到4-乙氧基-3-碘苯甲醛
  参考文献：
  名称：

  铁（III）催化的N-碘代琥珀酰亚胺活化对芳烃的高度区域选择性碘化

  摘要：

  已经开发了铁（III）催化的用于芳烃的快速和高度区域选择性碘化的方法。使用由氯化铁（III）原位生成的强力路易斯酸，三氟化铁（III）和易于获得的基于三氟化物的离子液体，可以在宽范围的温和条件下活化N-碘代琥珀酰亚胺（NIS）和有效的碘化作用底物，包括生物活性化合物和分子显像剂。

  DOI：

  10.1021/acs.orglett.5b02345

文献信息

• Highly Regioselective Iodination of Arenes via Iron(III)-Catalyzed Activation of <i>N</i>-Iodosuccinimide
  作者：Daugirdas T. Racys、Catherine E. Warrilow、Sally L. Pimlott、Andrew Sutherland

  DOI：10.1021/acs.orglett.5b02345

  日期：2015.10.2

  An iron(III)-catalyzed method for the rapid and highly regioselective iodination of arenes has been developed. Use of the powerful Lewis acid, iron(III) triflimide, generated in situ from iron(III) chloride and a readily available triflimide-based ionic liquid allowed activation of N-iodosuccinimide (NIS) and efficient iodination under mild conditions of a wide range of substrates including biologically

  已经开发了铁（III）催化的用于芳烃的快速和高度区域选择性碘化的方法。使用由氯化铁（III）原位生成的强力路易斯酸，三氟化铁（III）和易于获得的基于三氟化物的离子液体，可以在宽范围的温和条件下活化N-碘代琥珀酰亚胺（NIS）和有效的碘化作用底物，包括生物活性化合物和分子显像剂。
• [¹²⁵I/¹²⁷I]IodoHoechst 33342:  Synthesis, DNA Binding, and Biodistribution
  作者：Ravi S. Harapanhalli、Larry W. McLaughlin、Roger W. Howell、Dandamudi V. Rao、S. James Adelstein、Amin I. Kassis

  DOI：10.1021/jm9602672

  日期：1996.1.1

  An iodinated analog of the DNA-minor-groove-binding agent Hoechst 33342 has been synthesized and evaluated for DNA binding and tumor targeting. The bis-benzimidazole ring system of the title compound was constructed from the piperazinyl terminus via a Pinner-type cyclization followed by oxidative cyclization of the diamine Schiff base. To synthesize radioiodoHoechst 33342, (trimethylstannyl)Hoechst 33342 was prepared by the same strategy and subjected to mild radioiodedestannylation in the presence of lactoperoxidase. After purification by HPLC, the radiochemical was separated in carrier-free form with >85% radiochemical yield and >99% chemical and radiochemical purity. Fluorescence spectrometric analysis of the binding of iodoHoechst 33342 calf thymus DNA gave an equilibrium association constant (K-a) of 2.57 x 10(7) M(-1) comparable to the K-a value of Hoechst 33342. Fluorescence microscopy of viable V79 cells demonstrated that the iodinated dye stained the nuclei with avidity similar to that of the noniodinated dye. The biodistribution of [I-125]-iodoHoechst 33342 in LS174T tumor-bearing athymic mice 4 h postadministration showed a tumor uptake of 3-4% injected dose per gram (ID/g), tumor/blood ratio of 6-8, and tumor/nontumor ratios above unity for most organs. A low thyroid uptake (similar to 2% ID/g) indicated that the radiochemical did not deiodinate and was stable in vivo.
• 10.1039/d4ob00603h
  作者：Wu, Fufang、Tang, Chunmei、Li, Xuejian、Li, Nan、Liu, Miao、Li, Danqin、Dai, Rongrong、Shen, Xiaobao、Zhai, Hongbin

  DOI：10.1039/d4ob00603h

  日期：——

  iodination. The selection of appropriate environmentally friendly and cost-effective oxidants in combination with iodine for the iodination of aromatic rings, along with its application in the synthesis of natural products, holds significant importance. A highly efficient method utilizing I(III) as the initiator has been successfully developed for monoiodination of arylaldehydes. The method demonstrates good

  碘是芳香族化合物碘化最有效的来源之一；然而，其亲电性不足以直接碘化。选择合适的环保且经济有效的氧化剂与碘结合用于芳环的碘化，及其在天然产物合成中的应用具有重要意义。已成功开发出一种利用 I( III ) 作为引发剂进行芳醛单碘化的高效方法。该方法与多种（杂）芳香醛具有良好的相容性，从而产生中等至优异的产率，且无需任何有毒、挥发性或爆炸性试剂。通过碘化和乌尔曼型偶联，合成了七种天然产物，即 aristogins A–F 和 Hernandial。