4-Benzyloxy-phthalsaeure-dimethylester | 5840-67-5

• 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: 4-Benzyloxy-phthalsaeure-dimethylester
• 英文别名: Dimethyl 4-(benzyloxy)phthalate；dimethyl 4-phenylmethoxybenzene-1,2-dicarboxylate
• CAS: 5840-67-5
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: RNGQUAIRELDUCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-Benzyloxy-phthalsaeure-dimethylester 在 lithium aluminium tetrahydride 、 戴斯-马丁氧化剂 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 4-Phenylmethoxyphthalaldehyde
  参考文献：
  名称：

  Convenient syntheses of fluorous phenols of the formula HOC6H5−n((CH2)3(CF2)7CF3)n (n=1, 2) and the corresponding triarylphosphites

  摘要：

  The aldehydic benzyl ethers PhCH2OC6H4CHO (2; a/b = para/meta series) are readily available from the corresponding phenols and react with Wittig reagents derived from LPh3PCH2CH2Rf8]I-+(-) (R-f8 = (CF2)(7)CF3) to give PhCH2OC6H4CH=CHCH2Rf8 (86-93%, Z major). Reactions with H-2 over Pd/C give the fluorous phenols HOC6H4(CH2)(3)R-f8 (4a,b; 87-91%). Condensations with PCl3 and NEt3 (3.0:1.0:3.3 mol ratio) give the fluorous phosphites P[OC6H4(CH2)(3)R-f8](3) (5a,b; 92-94%), but traces of 4a,b are difficult to remove. The phthalate-based benzyl ethers PhCH2OC6H3 (COOR)(2) (7; c/d = 3,5/3,4 -OC6H3-3,n-(R)(2) series) are easily accessed and reduced with LiAlH4 to the diols PhCH2OC6H3(CH2OH)(2) (8c,d; 89-90%). Diol 8c and the Dess-Martin periodinane react to give the dialdehyde PhCH2OC6H3(CHO)(2) (9C; 95%). This is elaborated by a sequence analogous to 2 --> 4 --> 5 to the fluorous phenol HOC6H3((CH2)(3)R-f8)(2) (11C; 97%/96%, two steps) and phosphite P[OC6H3((CH2)(3)R-f8)(2)](3) (12c, 92%), from which traces of 11c are difficult to remove. Diol 8d can be similarly elaborated to 11d, but the dialdehyde 9d is labile and the combined yield of the Dess-Martin[Wittig steps is 32%. The CF3C6F11/toluene partition coefficients of 11c,d, and 12c (two pony tails; 70:30, 72:28, 92:8) are much higher than those of 4a and b (one pony tail; 12:88, 14:86). (C) 2002 Elsevier Science B.V.. All rights reserved.

  DOI：

  10.1016/s0022-1139(02)00242-7
• 作为产物：
  描述：

  4-羟基邻苯二甲酸 在 硫酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 15.0h， 生成 4-Benzyloxy-phthalsaeure-dimethylester
  参考文献：
  名称：

  Convenient syntheses of fluorous phenols of the formula HOC6H5−n((CH2)3(CF2)7CF3)n (n=1, 2) and the corresponding triarylphosphites

  摘要：

  The aldehydic benzyl ethers PhCH2OC6H4CHO (2; a/b = para/meta series) are readily available from the corresponding phenols and react with Wittig reagents derived from LPh3PCH2CH2Rf8]I-+(-) (R-f8 = (CF2)(7)CF3) to give PhCH2OC6H4CH=CHCH2Rf8 (86-93%, Z major). Reactions with H-2 over Pd/C give the fluorous phenols HOC6H4(CH2)(3)R-f8 (4a,b; 87-91%). Condensations with PCl3 and NEt3 (3.0:1.0:3.3 mol ratio) give the fluorous phosphites P[OC6H4(CH2)(3)R-f8](3) (5a,b; 92-94%), but traces of 4a,b are difficult to remove. The phthalate-based benzyl ethers PhCH2OC6H3 (COOR)(2) (7; c/d = 3,5/3,4 -OC6H3-3,n-(R)(2) series) are easily accessed and reduced with LiAlH4 to the diols PhCH2OC6H3(CH2OH)(2) (8c,d; 89-90%). Diol 8c and the Dess-Martin periodinane react to give the dialdehyde PhCH2OC6H3(CHO)(2) (9C; 95%). This is elaborated by a sequence analogous to 2 --> 4 --> 5 to the fluorous phenol HOC6H3((CH2)(3)R-f8)(2) (11C; 97%/96%, two steps) and phosphite P[OC6H3((CH2)(3)R-f8)(2)](3) (12c, 92%), from which traces of 11c are difficult to remove. Diol 8d can be similarly elaborated to 11d, but the dialdehyde 9d is labile and the combined yield of the Dess-Martin[Wittig steps is 32%. The CF3C6F11/toluene partition coefficients of 11c,d, and 12c (two pony tails; 70:30, 72:28, 92:8) are much higher than those of 4a and b (one pony tail; 12:88, 14:86). (C) 2002 Elsevier Science B.V.. All rights reserved.

  DOI：

  10.1016/s0022-1139(02)00242-7

文献信息

• Small Molecule Inhibitors of the BfrB–Bfd Interaction Decrease <i>Pseudomonas aeruginosa</i> Fitness and Potentiate Fluoroquinolone Activity
  作者：Achala N. D. Punchi Hewage、Huili Yao、Baskar Nammalwar、Krishna Kumar Gnanasekaran、Scott Lovell、Richard A. Bunce、Kate Eshelman、Sahishna M. Phaniraj、Molly M. Lee、Blake R. Peterson、Kevin P. Battaile、Allen B. Reitz、Mario Rivera

  DOI：10.1021/jacs.9b00394

  日期：2019.5.22

  inhibitors of the BfrB–Bfd protein–protein interaction. The process was initiated by screening a fragment library and followed by obtaining the structure of a fragment hit bound to BfrB. The structural insights were used to develop a series of 4-(benzylamino)- and 4-((3-phenylpropyl)amino)-isoindoline-1,3-dione analogs that selectively bind BfrB at the Bfd binding site. Challenging P. aeruginosa cells with

  储铁蛋白细菌铁蛋白 (BfrB) 是细菌铁稳态的核心。从 BfrB 中动员铁，这需要通过同源铁氧还蛋白 (Bfd) 结合，对于调节铜绿假单胞菌中的细胞溶质铁水平至关重要。本文描述了 BfrB-Bfd 蛋白质-蛋白质相互作用的小分子抑制剂的结构引导开发。该过程通过筛选片段文库开始，然后获得与 BfrB 结合的片段命中结构。结构见解用于开发一系列 4-(苄基氨基)-和 4-((3-苯基丙基)氨基)-isoindoline-1,3-dione 类似物，它们在 Bfd 结合位点选择性结合 BfrB。用 4 取代异二氢吲哚类似物挑战铜绿假单胞菌细胞显示出剂量依赖性生长表型。进一步的研究确定，这些类似物引发了一种pyoverdin 过度生产表型，这与 BfrB-Bfd 相互作用的阻断和随之而来的铁在 BfrB 中的不可逆积累一致，伴随着细胞质中铁的消耗。通过在天然 PAGE 凝胶上分离的铜绿假单胞菌细胞裂解物中的
• A Systematic Study of Peripherally Multiple Aromatic Ester-Functionalized Poly(benzyl ether) Dendrons for the Fabrication of Organogels: Structure-Property Relationships and Thixotropic Property
  作者：Yu Feng、Zhi-Xiong Liu、Hui Chen、Zhi-Chao Yan、Yan-Mei He、Chen-Yang Liu、Qing-Hua Fan

  DOI：10.1002/chem.201400157

  日期：2014.6.2

  A new class of peripherally multiple aromatic ester‐functionalized poly(benzyl ether) dendrons and/or dendrimers with different focal point substituents, surface groups, interior structures, as well as different generations have been synthesized and their structure–property relationships with respect to their gelation ability have been investigated systematically. Most of these dendrons are able to

  合成了具有不同焦点取代基，表面基团，内部结构以及不同世代的一类新型的由外围芳族酯官能化的聚（苄基醚）树枝状和/或树枝状大分子，并且它们之间的结构-性质关系系统地研究了胶凝能力。这些树突中的大多数都能够在很宽的极性范围内凝胶化有机溶剂。不仅在胶凝能力上而且在热致，形态和流变学特征中均观察到明显的树突作用。公开了外围酯官能度和内部树状结构的细微变化显着影响了树突的胶凝行为。在研究的所有树突中，第二代和第三代树突以邻苯二甲酸间苯二甲酸二甲酯（DMIP）为外围基团的G 0 G 2 -Me和G 0 G 3 -Me表现出最佳的胶凝能力，并且在22种以上的芳香族和极性有机溶剂中形成了稳定的凝胶。最低临界胶凝浓度（CGC）达到2.0 mg mL -1，表明一个树枝状分子可截留约1.35×10 4个溶剂分子。通过结合单晶/粉末X射线衍射（XRD）分析和浓度依赖性（CD）/温度依赖性（TD）1来进一步研究凝胶形成的驱动力11