2-Hydroxy-4-<(2-methoxyethoxy)methoxy>benzaldehyd | 141330-33-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Hydroxy-4-<(2-methoxyethoxy)methoxy>benzaldehyd
• 英文别名: 4-((2-methoxyethoxy)methoxy)-2-hydroxybenzaldehyde；2-hydroxy-4-(2-methoxyethoxymethoxy)benzaldehyde
• CAS: 141330-33-8
• 化学式: C₁₁H₁₄O₅
• 分子量: 226.229
• InChiKey: PLKIFSBDVMEFGA-UHFFFAOYSA-N

物化性质

• 沸点：
  363.2±37.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  左旋-反式-1,2-环己二胺盐酸盐 、 2-Hydroxy-4-<(2-methoxyethoxy)methoxy>benzaldehyd 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以96%的产率得到2-[[(1R,2R)-2-[[2-hydroxy-4-(2-methoxyethoxymethoxy)phenyl]methylideneamino]cyclohexyl]iminomethyl]-5-(2-methoxyethoxymethoxy)phenol
  参考文献：
  名称：

  设计形成多金属配合物的手性塞伦配体

  摘要：

  已经设计了能够形成多金属络合物的手性salen配体。所述配体在4,4'-位具有取代基，但在3,3'-位不具有取代基，以允许第二金属离子接近所述沙伦氧原子。制备了其中聚醚链连接4,4'-位的配体，并与铜络合。另外，制备了在4,4'-位具有潜在金属配位取代基的无环配体，并与铜和钴络合。一种钴配合物的晶体结构表明它是三金属配合物，其中Co（II）（OAc）2基团与两个Co（III）（salen）（OAc）单元的赛伦氧原子配位。相反，Co的晶体结构（沙仑）复合物与叔发现连接到3,3'-位的丁基是单核的。测试了所有络合物作为丙氨酸甲酯不对称烷基化的不对称相转移催化剂，形成了具有高达85％ee的（R）-α-甲基苯基丙氨酸甲酯。

  DOI：

  10.1016/j.tet.2011.10.084
• 作为产物：
  描述：

  2,4-Bis<(2-methoxyethoxy)methoxy>benzaldehyd 在 zinc(II) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 以26%的产率得到2-Hydroxy-4-<(2-methoxyethoxy)methoxy>benzaldehyd
  参考文献：
  名称：

  Positional chemoselectivity in the Zn(II)-mediated removal of phenol protecting groups

  摘要：

  A protocol was developed for the chemoselective ortho-deprotection of polyphenolic substrates using readily available (ZnX2)-X-II salts. This procedure provides exceptional positional selectivity for the deprotection of phenols that reside adjacent to directing carbonyl functionality in the presence of similar protecting groups at the meta and para positions. Good to excellent yields of the desired free phenols were obtained (<= 96%), and a wide assortment of protecting groups was readily removed under the reaction conditions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.103

文献信息

• Synthese und Reaktionsverhalten 2′-substituierter Isoflavone
  作者：Manfred Süsse、Siegfried Johne、Manfred Hesse

  DOI：10.1002/hlca.19920750205

  日期：1992.3.18

  Synthesis and Behaviour of Isoflavones Substituted in 2′-Position

  异黄酮在2′-位取代的合成及行为
• Inhibitors of DNA polymerase β: Activity and mechanism
  作者：Zhijie Gao、David J. Maloney、Larisa M. Dedkova、Sidney M. Hecht

  DOI：10.1016/j.bmc.2008.02.071

  日期：2008.4

  Bioassay-guided fractionation of extracts prepared from Couepia polyandra and Edgeworthia gardneri resulted in the isolation of the DNA polymerase beta (pol beta) inhibitors oleanolic acid (1), edgeworin (2), betulinic acid (3), and stigmasterol (4). Study of these pol b inhibitors revealed that three of them inhibited both the lyase and polymerase activities of DNA polymerase beta, while stigmasterol inhibited only the lyase activity. Further investigation indicated that the four inhibitors had substantially different effects on the DNA-pol beta binary complex that is believed to be an obligatory intermediate in the lyase reaction. It was found that the inhibitors potentiated the inhibitory action of the anticancer drug bleomycin in cultured A549 cells, without any influence on the expression of pol beta in the cells. The results of the unscheduled DNA synthesis assay support the thesis that the potentiation of bleomycin cytotoxicity by DNA pol beta inhibitors was a result of an inhibition of DNA repair synthesis. (C) 2008 Elsevier Ltd. All rights reserved.
• Benzofuran-Derived Cyclic β-Amino Acid Scaffold for Building a Diverse Set of Flavonoid-Like Probes and the Discovery of a Cell Motility Inhibitor
  作者：Jyoti P. Nandy、Bojana Rakic、Bugga V. N. B. Sarma、Nallareddy Babu、Marc Lefrance、Gary D. Enright、Donald M. Leek、Kate Daniel、Luc A. Sabourin、Prabhat Arya

  DOI：10.1021/ol800050g

  日期：2008.3.1

  We report here a practical, enantioselective synthesis of benzofuran-derived, cyclic trans-beta-amino acid scaffold. In two cases, tricyclic derivatives having six- and eight-membered unsaturated lactams were obtained from this versatile scaffold. To explore the biological applications, these compounds were subjected to cell-based assays, using NIH3T3 mouse cells to examine their potency as cell motility inhibitors and identified 18 as a potent cell motility inhibitor (IC(50) approximate to 40 mu M in chamber cell migration assay).