5-methoxy-2-(methoxymethoxy)benzaldehyde | 73220-20-9

• 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: 5-methoxy-2-(methoxymethoxy)benzaldehyde
• 英文别名: 2-methoxymethoxy-5-methoxybenzaldehyde；5-methoxy-2-methoxymethoxybenzaldehyde
• CAS: 73220-20-9
• 化学式: C₁₀H₁₂O₄
• mdl: MFCD21195359
• 分子量: 196.203
• InChiKey: WSMHWPOBGUNBJR-UHFFFAOYSA-N

物化性质

• 沸点：
  132-134 °C(Press: 1.5 Torr)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methoxy-2-(methoxymethoxy)benzaldehyde 在 吡啶 、 六甲基磷酰三胺 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 二甲基硫 、 sodium hydride 、 对苯二酚 、 lithium hexamethyldisilazane 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 20.92h， 生成 2-((2,6-dimethyl-6-(4-methylpenta-1,3-dienyl)cyclohex-2-enyl)methyl)-4-methoxy-1-(methoxymethoxy)benzene
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel riccardiphenol analogs

  摘要：

  A novel, facile, high yield, and less cumbersome synthesis of riccardiphenol, analogs is described. The synthesized compounds were characterized and assessed for its in vitro activity in a panel of human cancer cell lines of differing origin: HuCCT-1, BxPC3, Panc-1, Mia-Paca, A431, Hep2, and HN006. HuCCT-1 was derived from an intrahepatic cholangiocarcinoma; BxPC3, Mia-Paca, and Panc-1 were derived from pancreatic cancers; A431 was derived from a vulvar epithelial carcinoma; and Hep2 and HN006 were derived from squamous cell carcinomas of the head and neck. The cytotoxicity of a newly developed riccardiphenol analog against human cancer cell lines was assessed. The cancer cells exhibited varying sensitivities to the compound, with IC50 values from 30 to 50 mu M. This susceptibility was particularly interesting in the case of lines such as Hep2 and BxPC3 that are resistant to classic cytotoxic drugs as well as some targeted agents. These results demonstrate that the novel riccardiphenol analog has effective action against human-derived cancer cell in vitro. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.010
• 作为产物：
  描述：

  4-甲氧基苯酚 在 正丁基锂 、 sodium hydride 作用下， 以 乙醚 为溶剂， 反应 3.5h， 生成 5-methoxy-2-(methoxymethoxy)benzaldehyde
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel riccardiphenol analogs

  摘要：

  A novel, facile, high yield, and less cumbersome synthesis of riccardiphenol, analogs is described. The synthesized compounds were characterized and assessed for its in vitro activity in a panel of human cancer cell lines of differing origin: HuCCT-1, BxPC3, Panc-1, Mia-Paca, A431, Hep2, and HN006. HuCCT-1 was derived from an intrahepatic cholangiocarcinoma; BxPC3, Mia-Paca, and Panc-1 were derived from pancreatic cancers; A431 was derived from a vulvar epithelial carcinoma; and Hep2 and HN006 were derived from squamous cell carcinomas of the head and neck. The cytotoxicity of a newly developed riccardiphenol analog against human cancer cell lines was assessed. The cancer cells exhibited varying sensitivities to the compound, with IC50 values from 30 to 50 mu M. This susceptibility was particularly interesting in the case of lines such as Hep2 and BxPC3 that are resistant to classic cytotoxic drugs as well as some targeted agents. These results demonstrate that the novel riccardiphenol analog has effective action against human-derived cancer cell in vitro. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.010

文献信息

• [EN] SUBSTITUTED BENZALDEHYDE COMPOUNDS AND METHODS FOR THEIR USE IN INCREASING TISSUE OXYGENATION<br/>[FR] COMPOSÉS BENZALDÉHYDE SUBSTITUÉS ET PROCÉDÉS D'UTILISATION DE CEUX-CI DANS L'AUGMENTATION DE L'OXYGÉNATION DES TISSUS
  申请人：GLOBAL BLOOD THERAPEUTICS INC

  公开号：WO2013102142A1

  公开（公告）日：2013-07-04

  Provided are substituted benzaldehydes and derivatives thereof that act as allosteric modulators of hemoglobin, methods and intermediates for their preparation, pharmaceutical compositions comprising the modulators, and methods for their use in treating disorders mediate by hemoglobin and disorders that would benefit from increased tissue oxygenation.

  提供了替代苯甲醛及其衍生物，其作为血红蛋白的变构调节剂，以及其制备的方法和中间体，包括这些调节剂的药物组合物，以及在治疗由血红蛋白介导的疾病和需要增加组织氧合的疾病中使用它们的方法。
• Pt(IV)-catalyzed generation and [4+2]-cycloaddition reactions of o-quinone methides
  作者：Suttipol Radomkit、Pakornwit Sarnpitak、Jumreang Tummatorn、Paratchata Batsomboon、Somsak Ruchirawat、Poonsakdi Ploypradith

  DOI：10.1016/j.tet.2011.03.059

  日期：2011.5

  Novel intermolecular and intramolecular generations of ortho-quinone methides and their formal [4+2]-cycloaddition reactions with olefins catalyzed by PtCl4 and AuCl3 under mild conditions have been developed. Good to excellent yields (up to 99%) and diastereoselectivity (up to >99:1) of the chromans were obtained. PtCl4 was found to be effective and compatible with various functional groups present

  已经开发了新的分子间和分子内生成的邻醌甲基化物及其在温和条件下与PtCl 4和AuCl 3催化的烯烃的正式[4 + 2]-环加成反应。获得了良好的品色（高达99％）和非对映体选择性（高达> 99：1）的苯并二氢吡喃。发现PtCl 4是有效的并且与存在于底物中的各种官能团相容。提出并讨论了其催化循环的机理。
• The Baeyer-Villiger Oxidation of Aromatic Aldehydes and Ketones with Hydrogen Peroxide Catalyzed by Selenium Compounds. A Convenient Method for the Preparation of Phenols
  作者：Ludwik Syper

  DOI：10.1055/s-1989-27183

  日期：——

  A series of organoselenium compounds was investigated as activators of hydrogen peroxide in the Baeyer-Villiger oxidation. As a result, a convenient and cheap method for transformation of aromatic aldehydes, having polycondensed ring systems or electron-donating substituents, and polymethoxy derivatives of acetophenone, into phenols was elaborated. This method utilizes hydrogen peroxide activated by areneseleninic acids, as oxidizing agent.

  一系列有机硒化合物被研究作为过氧化氢在拜耳-维利格氧化反应中的活化剂。结果发现，这是一种方便且经济的转化具有聚合环系或供电子取代基的芳香醛、乙酰苯的多甲氧基衍生物为酚类的方法。该方法使用由芳硒酸活化的过氧化氢作为氧化剂。
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  作者：Olga A. Ivanova、Vladimir A. Andronov、Vladimir S. Vasin、Alexey N. Shumsky、Victor B. Rybakov、Leonid G. Voskressensky、Igor V. Trushkov

  DOI：10.1021/acs.orglett.8b03491

  日期：2018.12.21

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• Ni-Catalyzed Cycloisomerization between 3-Phenoxy Acrylic Acid Derivatives and Alkynes via Intramolecular Cleavage and Formation of the C–O Bond To Give 2,3-Disubstituted Benzofurans
  作者：Shohei Ohno、Jiawei Qiu、Ray Miyazaki、Hiroshi Aoyama、Kenichi Murai、Jun-ya Hasegawa、Mitsuhiro Arisawa

  DOI：10.1021/acs.orglett.9b03170

  日期：2019.10.18

  based on transition-metal-catalyzed C-O bond cleavage have attracted much attention as a new synthetic method. Until now, several intermolecular reactions via C-O bond cleavage of aryl ethers, alkenyl ethers, esters, and others have been reported. Here we report an unprecedented C-O bond cleavage of 3-phenoxy acrylic acid derivatives, followed by intramolecular C-O bond formation with alkynes. This reaction

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