4-(3-溴丙氧基)苯甲酸乙酯 | 74226-00-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(3-溴丙氧基)苯甲酸乙酯
• 英文名称: ethyl 4-(3-bromopropoxy)benzoate
• CAS: 74226-00-9
• 化学式: C₁₂H₁₅BrO₃
• 分子量: 287.153
• InChiKey: CBDJGPFGNAKUAM-UHFFFAOYSA-N

物化性质

• 沸点：
  128-132 °C(Press: 0.1 Torr)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3-溴丙氧基)苯甲酸乙酯 在 乙醇 、 sodium ethanolate 、 sodium 作用下， 以 乙醇 为溶剂， 反应 10.17h， 生成 4-[3-(2,4-Diamino-6-oxo-1,6-dihydro-pyrimidin-5-yl)-propoxy]-benzoic acid ethyl ester
  参考文献：
  名称：

  5,6,7,8-四氢叶酸-潜在抗肿瘤药的开链类似物的合成和生物学活性。

  摘要：

  这项研究描述了嘌呤从头生物合成抑制剂的合成及其体外抗肿瘤活性，这些抑制剂是N- [4-[[3-（2,4-diamino-1,6-dihydro-6-oxo-5-pyrimidinyl ）丙基]氨基]苯甲酰基-L-谷氨酸（5-DACTHF）。通过关键的还原胺化步骤，由保护的嘧啶基丙醛和取代的谷氨酸苯甲酸酯部分合成苯环取代的类似物。由对氨基苯甲酸或类似物逐步构建嘧啶和连接链取代的类似物。测试这些化合物作为甲氨蝶呤摄取的抑制剂，作为与减少的叶酸转运系统的结合的量度，作为甘氨酰胺核糖核苷酸转化酶的抑制剂，作为叶酰聚谷氨酸合成酶的底物，以及作为细胞培养中肿瘤细胞生长的抑制剂。除了2' -F取代基，环取代的类似物的活性低于母体化合物。用碳，硫或氧替代10-氮对体外生物活性的影响不到2倍。嘧啶环上2位的四原子连接链和一个氨基对于良好的活性很重要。

  DOI：

  10.1021/jm00086a008
• 作为产物：
  描述：

  过氧化氢酶 、 1,3-二溴丙烷 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 4-(3-溴丙氧基)苯甲酸乙酯
  参考文献：
  名称：

  Novel 3-dodecanoylindole-2-carboxylic acid inhibitors of cytosolic phospholipase A2

  摘要：

  Derivatives of 1-[2-(4-carboxyphenoxy)ethyl]-3-dodecanoylindole-2-carboxylic acid (4) with modified substituents at the indole-1-position were synthesized and evaluated for their ability to inhibit the arachidonic acid release in human platelets mediated by the cytosolic phospholipase A(2). One of the most active compounds obtained was 26 with an IC50 of 0.44 muM. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00472-3

文献信息

• Copper-Promoted Trifluoromethylation of Primary and Secondary Alkylboronic Acids
  作者：Jun Xu、Bin Xiao、Chuan-Qi Xie、Dong-Fen Luo、Lei Liu、Yao Fu

  DOI：10.1002/anie.201206681

  日期：2012.12.7

  New couple: The Cu‐promoted trifluoromethylation of primary and secondary alkylboronic acids with TMSCF3 extends the scope of transition‐metal‐catalyzed trifluoromethylation reactions to sp3‐hybridized carbon centers. It also represents one of the first examples for Cu‐catalyzed CC cross‐coupling reactions of alkylboronic acid derivatives.

  新夫妇：用TMSCF 3的铜促进的伯烷基硼酸和仲烷基硼酸的三氟甲基化将过渡金属催化的三氟甲基化反应的范围扩展到了sp 3杂化的碳中心。它也代表的用于第一实施例中一个的Cu催化的Ç  C交叉耦合烷基硼酸衍生物的反应。
• Structure-Activity Relationship Studies of 1-Substituted 3-Dodecanoylindole-2-carboxylic Acids as Inhibitors of Cytosolic Phospholipase A2-Mediated Arachidonic Acid Release in Intact Platelets
  作者：Klaus Griessbach、Monika Klimt、Alwine Schulze Elfringhoff、Matthias Lehr

  DOI：10.1002/ardp.200290008

  日期：2002.12

  A series of 3‐dodecanoylindole‐2‐carboxylic acid derivatives with varied carboxylic acid substituents at the indole 1‐position were synthesized and evaluated for their ability to inhibit arachidonic acid release in human platelets mediated by the cytosolic phospholipase A2. Structure‐activity relationship studies revealed that increasing the polarity of these substituents by the introduction of additional

  合成了一系列在吲哚 1-位具有不同羧酸取代基的 3-十二酰基吲哚-2-羧酸衍生物，并评估了它们抑制细胞溶质磷脂酶 A2 介导的人血小板中花生四烯酸释放的能力。构效关系研究表明，通过在羧酸部分附近引入额外的极性基团来增加这些取代基的极性会降低活性。吲哚-1-羧酸替代物在不同位置的构象限制以及这些残基的长度延长导致化合物的效力没有显着差异。
• Glutamic acid derivatives
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0409382A1

  公开（公告）日：1991-01-23

  The present invention relates to compounds of formula (I): wherein Y is sulphur or oxygen; R² and R³ are the same or different and are hydrogen or C₁₋₄ alkyl; R⁴ is NR¹¹R¹²; R¹¹, R¹², R⁵ and R⁶ are the same or different and are hydrogen, C₁₋₄ alkyl or C₁₋₁₂ acyl; R⁷, R⁸, R⁹ and R¹⁰ are the same or different and are hydrogen, halo, C₁₋₄ haloalkyl, C₁₋₄ alkyl and C₁₋₄ alkoxy; and n is 2, 3, 4 or 5; m is 0 or an integer from 1 to 5; or a salt thereof, methods for the preparation of the compounds of the formula (I), pharmaceutical formulations containing them, and their use in the treatment of neoplastic growth.

  本发明涉及式(I)化合物： 其中 Y 是硫或氧；R² 和 R³ 相同或不同，并且是氢或 C₁₋₄ 烷基；R⁴ 是 NR¹¹R¹²；R¹¹、R¹²、R⁵和R⁶相同或不同，并且是氢、C₁₋₄烷基或 C₁₋₁₂酰基；R⁷、R⁸、R⁹和R¹⁰相同或不同，并且是氢、卤代、C₁₋₄卤代烷基、C₁₋₄烷基和C₁₋₄烷氧基；以及n是2、3、4或5；m是0或1至5的整数；或其盐，式（I）化合物的制备方法，含有它们的药物制剂，以及它们在治疗肿瘤生长中的用途。
• Fluorination Triggers Fluoroalkylation: Nucleophilic Perfluoro‐ <i>tert</i> ‐butylation with 1,1‐Dibromo‐2,2‐bis(trifluoromethyl)ethylene (DBBF) and CsF
  作者：Qian Wang、Quan Tao、Hui Dong、Chuanfa Ni、Xiaoming Xie、Jinbo Hu

  DOI：10.1002/anie.202113727

  日期：2021.12.20

  AbstractPerfluoro‐tert‐butylation reaction has long remained a challenging task. We now report the use of 1,1‐dibromo‐2,2‐bis(trifluoromethyl)ethylene (DBBF) as a practical reagent for perfluoro‐tert‐butylation reactions for the first time. Through a consecutive triple‐fluorination process with DBBF and CsF, the (CF3)3C− species can be liberated and observed, which is able to serve as a robust nucleophilic perfluoro‐tert‐butylating agent for various electrophiles. The power of this synthetic protocol is evidenced by the efficient synthesis of structurally diverse perfluoro‐tert‐butylated molecules. Multiple applications demonstrate the practicability of this method, as well as the superiority of perfluoro‐tert‐butylated compounds as sensitive probes. The perfluoro‐tert‐butylated product was successfully applied in 1H‐ and 19F‐magnetic resonance imaging (MRI) experiment with an ultra‐low field (ULF) MRI system.
• Selective thromboxane synthetase inhibitors. 1. 1-[(Aryloxy)alkyl]-1H-imidazoles
  作者：Peter E. Cross、Roger P. Dickinson、M. John Parry、Michael J. Randall

  DOI：10.1021/jm00148a009

  日期：1985.10

  1-(2-Phenoxyethyl)-1H-imidazole was found to be an inhibitor of thromboxane (TxA2) synthetase, but it also inhibited the adrenal cytochrome P-450 enzyme steroid 11 beta-hydroxylase. The preparation of a series of analogues is described, and activity against TxA2 synthetase, PGI2 synthetase, cyclooxygenase, and steroid 11 beta-hydroxylase is discussed. Potency against TxA2 synthetase was increased by introduction of a carboxyl group at a suitable distance from the imidazole ring. A distance of 8.1-8.8 A between N-1 of the imidazole and the carboxyl carbon was found to be optimal. Introduction of a carboxyl group also had the effect of reducing activity against steroid 11 beta-hydroxylase. The most potent and selective compound was found to be 4-[2-(1H-imidazol-1-yl) ethoxy]benzoic acid (14).