4-(benzyloxy)-3-iodobenzaldehyde | 74994-62-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(benzyloxy)-3-iodobenzaldehyde
• 英文别名: 3-Iodo-4-phenylmethoxybenzaldehyde
• CAS: 74994-62-0
• 化学式: C₁₄H₁₁IO₂
• 分子量: 338.145
• InChiKey: LFBVGTWHSFEHHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(benzyloxy)-3-iodobenzaldehyde 在 sodium tetrahydroborate 、 三溴化磷 、 双(三甲基硅烷基)氨基钾 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 7-(benzyloxy)-1-[4-(benzyloxy)-3-iodobenzyl]-8-bromo-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  模块化获取（±）-Tubocurine和（±）-Curine-形式的全合成Tubocurarine

  摘要：

  两个连续的Cu催化的Ullmann型C–O偶联允许首次成功地进入库雷拉生物碱（±）-管状尿素和（±）-尿素。从香兰素开始，合成序列包括15个线性步骤，并且包括总共24个转化。此外，tubocurine的总合成代表了著名的箭毒生物碱tubocurarine的正式总合成。

  DOI：

  10.1021/acs.joc.6b02647
• 作为产物：
  描述：

  3-碘-4-甲氧基苯甲醛 在 三溴化硼 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 4-(benzyloxy)-3-iodobenzaldehyde
  参考文献：
  名称：

  模块化获取（±）-Tubocurine和（±）-Curine-形式的全合成Tubocurarine

  摘要：

  两个连续的Cu催化的Ullmann型C–O偶联允许首次成功地进入库雷拉生物碱（±）-管状尿素和（±）-尿素。从香兰素开始，合成序列包括15个线性步骤，并且包括总共24个转化。此外，tubocurine的总合成代表了著名的箭毒生物碱tubocurarine的正式总合成。

  DOI：

  10.1021/acs.joc.6b02647

文献信息

• Total Synthesis of 3′,3′′′-Binaringenin and Related Biflavonoids
  作者：Gustavo Seoane、Gabriel Sagrera

  DOI：10.1055/s-0030-1258140

  日期：2010.8

  The synthesis of natural 3′,3′′′-binaringenin and four related biflavonoids was performed in good overall yield (15-35%) starting from readily available phloroglucinol and 4-hydroxy- or 4-methoxybenzaldehyde. Preliminary results indicate that some of these compounds have an interesting activity against S. aureus. binaringenin - biapigenin - protecting groups - antibacterial activity

  从容易获得的间苯三酚和4-羟基-或4-甲氧基苯甲醛开始，以良好的总收率（15-35％）进行天然3'，3''-联萘宁和四种相关双黄酮的合成。初步结果表明，其中一些化合物对金黄色葡萄球菌具有有趣的活性。 Binaringenin-Biapigenin-保护基-抗菌活性
• Acidic Rearrangement of (Benzyloxy)chalcones: A Short Synthesis of Chamanetin
  作者：Gustavo Seoane、Gabriel Sagrera

  DOI：10.1055/s-0029-1217064

  日期：——

  Treatment of (benzyloxy)chalcones with trifluoroacetic acid in refluxing chloroform gave several new benzyl(hydroxy)flavanones in high yields and good regioselectivities. By using this procedure, we prepared the natural compound chamanetin in good yield from readily available reagents. benzylation - rearrangements - protecting groups - chamanetin - chalcones

  在回流的氯仿中用三氟乙酸处理（苄氧基）查耳酮以高收率和良好的区域选择性得到了几种新的苄基（羟基）黄酮。通过使用此程序，我们从容易获得的试剂中以高收率制备了天然化合物Chamanetin。 苄基化-重排-保护基-香豆素-查尔酮
• Metal-free iodination of arylaldehydes for total synthesis of aristogins A–F and hernandial
  作者：Fufang Wu、Chunmei Tang、Xuejian Li、Nan Li、Miao Liu、Danqin Li、Rongrong Dai、Xiaobao Shen、Hongbin Zhai

  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。
• Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure–activity relationships
  作者：Mauricio Cabrera、Macarena Simoens、Gabriela Falchi、M. Laura Lavaggi、Oscar E. Piro、Eduardo E. Castellano、Anabel Vidal、Amaia Azqueta、Antonio Monge、Adela López de Ceráin、Gabriel Sagrera、Gustavo Seoane、Hugo Cerecetto、Mercedes González

  DOI：10.1016/j.bmc.2007.03.031

  日期：2007.5

  A series of synthetic chalcones, flavanones, and flavones has been synthesized and evaluated for antitumor activity against the human kidney carcinoma cells TK-10, human mammary adenocarcinoma cells MCF-7 (estrogen receptor-positive), and human colon adenocarcinoma cells HT-29. The most active series is the chalcone ones with the best results against TK-10 and HT-29 cells. Fourteen out of 53 analyzed compounds resulted very active against at least two of the studied tumoral cells. Alkaline single cell gel electrophoresis, comet assay, was performed as a study of the chromosomal aberrations promoted by the compounds on normal cells. Four active and two inactive chalcones were studied in the comet assay against normal human kidney cells (HK-2). A structure-activity relationship analysis of these compounds was performed and for 4- and 3,4-disubstituted derivatives a quantitative correlation was obtained in the case of anti-HT-29 activity. (c) 2007 Published by Elsevier Ltd.
• Whiting, Donald A.; Wood, Andrew F., Journal of the Chemical Society. Perkin transactions I, 1980, p. 623 - 628
  作者：Whiting, Donald A.、Wood, Andrew F.

  DOI：——

  日期：——