4-(diethylamino)-2-(methoxymethoxy)benzaldehyde

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(diethylamino)-2-(methoxymethoxy)benzaldehyde
• 英文别名: 4-diethylamino-2-(methoxymethoxy)benzaldehyde
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: SSQHIQVCLHTCIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6-dimethoxy-2,2-dimethyl-2H-benzopyran 、 4-(diethylamino)-2-(methoxymethoxy)benzaldehyde 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以20 mg的产率得到8-(Diethylamino)-5-methoxy-2,2-dimethylpyrano[2,3-b]xanthen-11-one
  参考文献：
  名称：

  Multidimensional optimization of promising antitumor xanthone derivatives

  摘要：

  A promising antitumor xanthone derivative was optimized following a multidimensional approach that involved the synthesis of 17 analogues, the study of their lipophilicity and solubility, and the evaluation of their growth inhibitory activity on four human tumor cell lines. A new synthetic route for the hit xanthone derivative was also developed and applied for the synthesis of its analogues. Among the used cell lines, the HL-60 showed to be in general more sensitive to the compounds tested, with the most potent compound having a GI(50) of 5.1 mu M, lower than the hit compound. Lipophilicity was evaluated by the partition coefficient (K-p) of a solute between buffer and two membrane models, namely liposomes and micelles. The compounds showed a log K-p between 3 and 5 and the two membrane models showed a good correlation (r(2) = 0.916) between each other. Studies concerning relationship between solubility and structure were developed for the hit compound and 5 of its analogues. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.079
• 作为产物：
  描述：

  4-(二乙氨基)水杨醛 、 氯甲基甲基醚 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到4-(diethylamino)-2-(methoxymethoxy)benzaldehyde
  参考文献：
  名称：

  EP2123637

  摘要：

  公开号：

文献信息

• Formation of Furan Derivatives from Phenacyl Bromides and Sodium Telluride; Attempted Extension to Coumarin Synthesis
  作者：Seetharamaiyer Padmanabhan、Takuji Ogawa、Hitomi Suzuki

  DOI：10.1246/bcsj.62.2114

  日期：1989.6

  The enolates, generated from phenacyl bromides by sodium telluride, yield 2,4-diarylfurans in addition to the expected dehalogenation products. No 1,4-dicarbonyl compounds could be isolated even in the presence of excess oxidizing agent, copper(II) chloride. Condensation of 2-(methoxymethoxy)arenecarbaldehydes with ethyl bromoacetate in the presence of sodium telluride gave the expected α,β-unsaturated

  除了预期的脱卤产物外，由碲化钠从苯甲酰溴生成的烯醇化物还产生 2,4-二芳基呋喃。即使存在过量的氧化剂氯化铜 (II)，也无法分离出 1,4-二羰基化合物。在碲化钠存在下，2-(甲氧基甲氧基)芳烃甲醛与溴乙酸乙酯的缩合得到预期的α,β-不饱和酯，其抵抗环化以产生所需的香豆素衍生物。尝试进行 2-(溴乙酰氧基) 苯甲醛的分子内 Reformatsky 型反应，仅得到 6,12-环氧-6H,12H-二苯并[b,f]-[1,5] 二恶星作为主要产物。
• Pd(0)-Catalyzed Direct C−H Functionalization of 2-<i>H</i>-4-Benzylidene Imidazolones: Friendly and Large-Scale Access to GFP and Kaede Protein Fluorophores
  作者：Mickaël Muselli、Christine Baudequin、Cécile Perrio、Christophe Hoarau、Laurent Bischoff

  DOI：10.1002/chem.201600602

  日期：2016.4.11

  The first one‐pot synthesis of N‐substituted 2‐H‐4‐benzylidene imidazolones and their subsequent palladium‐catalyzed and copper‐assisted direct C2−H arylation and alkenylation with aryl‐ and alkenylhalides are described. This innovative synthesis is step‐economical, azide‐free, high yielding, highly flexible in the introduction of a variety of electronically different groups, and can be operated on

  描述了N-取代的2 H -4亚苄基咪唑酮的首次单锅合成及其随后的钯催化和铜辅助的直接C2-H芳基化和芳基和烯基卤化物的烯基化反应。这种创新的合成方法经济，省力，无叠氮化物，高收率，在引入各种电子形式不同的基团时具有高度的灵活性，并且可以大规模操作。此外，该方法允许直接访问基于C2芳基化或烯基化的咪唑酮绿色荧光蛋白（GFP）和Kaede蛋白荧光团，包括邻羟基化模型。
• NOVEL CURCUMIN DERIVATIVE
  申请人：Takahashi Takashi

  公开号：US20100048901A1

  公开（公告）日：2010-02-25

  The present invention provides a novel compound that is structurally similar to curcumin and has a suppressive effect on Aβ aggregation, a degradative effect on Aβ aggregates, an inhibitory effect on β-secretase, and a protective effect on neurons. The novel compound is a compound represented by the following general formula (Ia) or a salt thereof: wherein R 1 represents a 4-hydroxy-3-methoxyphenyl group or the like, and R 2 represents a 1H-indol-6-yl group or the like.

  本发明提供了一种新型化合物，其结构类似于姜黄素，并具有抑制Aβ聚集、降解Aβ聚集体、抑制β-分泌酶以及保护神经元的作用。该新型化合物是由以下通式(Ia)或其盐所表示的化合物：其中，R1表示4-羟基-3-甲氧基苯基或类似基团，R2表示1H-吲哚-6-基基或类似基团。
• Curcumin derivative
  申请人：Takahashi Takashi

  公开号：US08962674B2

  公开（公告）日：2015-02-24

  The present invention provides a novel compound that is structurally similar to curcumin and has a suppressive effect on Aβ aggregation, a degradative effect on Aβ aggregates, an inhibitory effect on β-secretase, and a protective effect on neurons. The novel compound is a compound represented by the following general formula (Ia) or a salt thereof: wherein R1 represents a 4-hydroxy-3-methoxyphenyl group or the like, and R2 represents a 1H-indol-6-yl group or the like.

  本发明提供了一种新型化合物，其结构类似于姜黄素，并具有抑制Aβ聚集、降解Aβ聚集物、抑制β-分泌酶和保护神经元的作用。该新型化合物是由以下一般式(Ia)表示的化合物或其盐：其中R1代表4-羟基-3-甲氧基苯基或类似物，R2代表1H-吲哚-6-基基或类似物。
• PADMANABHAN, SEETHARAMAIYER;OGAWA, TAKUJI;SUZUKI, HITOMI, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 2114-2116
  作者：PADMANABHAN, SEETHARAMAIYER、OGAWA, TAKUJI、SUZUKI, HITOMI

  DOI：——

  日期：——