2-(2-氯乙氧基)苯甲醛 | 54373-14-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(2-氯乙氧基)苯甲醛
• 英文名称: 2-(2-chloroethoxy)benzaldehyde
• CAS: 54373-14-7
• 化学式: C₉H₉ClO₂
• mdl: MFCD01961271
• 分子量: 184.622
• InChiKey: VJQZLVZNOAKWKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2913000090

反应信息

• 作为反应物：
  描述：

  2-(2-氯乙氧基)苯甲醛 在 sodium hydroxide 、 四丁基氟化铵 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  A Novel Approach to Dual-Acting Thromboxane Receptor Antagonist/Synthase Inhibitors Based on the Link of 1,3-Dioxane-Thromboxane Receptor Antagonists and -Thromboxane Synthase Inhibitors

  摘要：

  A new class of dual-acting racemic thromboxane receptor antagonist/thromboxane synthase inhibitors is reported, based on the novel approach of linking the known thromboxane synthase inhibitors (TXSI) dazoxiben (2) or isbogrel(11) (separately) to thromboxane receptor antagonists (TXRA) from the 1,3-dioxane series, such as ICI 192605 (10). Dual activity was observed in vitro with inhibition of human microsomal thromboxane synthase in the range IC50 = 0.01-1.0 mu M and receptor antagonist activity by inhibition of U46619-induced human platelet aggregation in the range pA(2) = 5.5-7.0. The in vitro results also showed that very large groups could be tolerated at the selected substitution positions of the TXRA and TXSI components. Oral activity was observed in ex vivo tests in both rats and dogs at a dose of 10 mg/kg. Thus, (E)-7-[4-[[4-[(2SR,4SR,5RS)-5-[(Z)-5-carboxypent-2-enyl]-4-(2-hydroxyphenyl)-1,3-dioxan-2-yl]benzyl]oxy]phenyl]-7-(3-pyridyl)hept-6-enoic acid (110) was both an antagonist (pA(2) = 6.7) and a synthase inhibitor (IC50 = 0.02 mu M). On oral dosing (10 mg/kg) to rats and dogs, 110 showed significant TXRA activity [concentration ratio >64 (rat, 3 h) and >59 +/- 11.3 (dog, 2 h) vs ex vivo U46619-induced platelet aggregation]. Inhibition of thromboxane synthase at the respective time points in these experiments was 81 +/- 4.4% (rat) and 69 +/- 4.8% (dog).

  DOI：

  10.1021/jm00010a005
• 作为产物：
  描述：

  2-氯乙基对甲苯磺酸酯 、 水杨醛 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 68.0h， 以86%的产率得到2-(2-氯乙氧基)苯甲醛
  参考文献：
  名称：

  Synthesis of 2-phenylthiazolidine derivatives as cardiotonic agents. II. 2-(Phenylpiperazinoalkoxyphenyl)thiazolidine-3-thiocarboxamides and the corresponding carboxamides.

  摘要：

  大量2-（苯基哌嗪基烷氧苯基）噻唑烷-3-硫代羧酰胺及其相应羧酰胺（II）被合成并在麻醉犬中测试其强心活性。化合物II通过羟基苯甲醛（III）及其中间体（IV、V和X）制备。通过改变结构参数来研究结构-活性关系（SAR）。将哌嗪基烷氧基团从邻位位置移至间位或对位导致活性显著下降。将硫代羧酰胺转变为羧酰胺基团导致活性显著增加。这种趋势在这一系列化合物中普遍存在，并构成与简单2-苯基噻唑烷系列SAR的主要偏离。关于氨基烷氧链长度的影响，乙氧基衍生物通常比更高级的类似物更有效。在（硫代）羧酰胺基团中延长N-烷基通常导致活性下降。在合成的各种衍生物中，II15被发现其效力约为氨力农的一百倍，且作用时间较长。

  DOI：

  10.1248/cpb.35.2394

文献信息

• Improved glucose tolerance in rats treated with oxazolidinediones
  作者：Rodney C. Schnur、Malcolm Morville

  DOI：10.1021/jm00155a030

  日期：1986.5

  5-(2-Chloro-6-methoxyphenyl)oxazolidine-2,4-dione (49) is the most potent agent selected from a series of 5-substituted oxazolidinediones that were found to cause improvements in glucose tolerance in previously fasted rats and potentiation of insulin release in response to a glucose challenge. These compounds were unique in not producing hypoglycemia below the normal fasting glycemia levels. Substituent

  5-（2-氯-6-甲氧基苯基）恶唑烷-2,4-二酮（49）是选自一系列5-取代的恶唑烷二酮类中最有效的药物，已发现这些物质可改善先前禁食的大鼠的葡萄糖耐量和增强能力响应葡萄糖激发的胰岛素释放。这些化合物的独特之处在于不会产生低于正常空腹血糖水平的低血糖。研究了苯环2-6位的取代基效应。发现替代的最佳位置是2-，5-和6-位。恶唑烷二酮环的变化通常导致活性降低。详细介绍了该系列的合成和构效关系。
• N-substituted-2-[2-[2-(4-p
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：US04689327A1

  公开（公告）日：1987-08-25

  A novel thiazolidine derivative of the formula: ##STR1## wherein R.sup.1 is a substituted or unsubstituted phenyl group, Q is a single bond, a lower alkylene group or a lower alkenylene group, R.sup.2 and R.sup.3 are the same or different and each is hydrogen atom, a lower alkyl group, a cycloalkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group, a lower alkylsulfonyl group, a benzoyl group, a phenyl group or a di(lower alkyl)phosphoryl group, Alk is a lower alkylene group, and Y and Z are the same or different and each is oxygen atom or sulfur atom, or a pharmaceutically acceptable salt thereof, which is useful as a cardiotonic agent is disclosed together with processes for the preparation of the compound and a pharmaceutical composition containing said compound.

  一种新的噻唑啉衍生物的化学式为：##STR1## 其中R.sup.1是取代或未取代的苯基，Q是一个单键，一个较低的烷基链或一个较低的烯基链，R.sup.2和R.sup.3相同或不同，每个都是氢原子，一个较低的烷基链，一个环烷基链，一个较低的烷酰基链，一个较低的烷氧羰基链，一个较低的烷基磺酰基链，一个苯甲酰基链，一个苯基或一个二(较低烷基)磷酰基链，Alk是一个较低的烷基链，Y和Z相同或不同，每个是氧原子或硫原子，或其药学上可接受的盐，该化合物可用作心力衰竭药物，还公开了制备该化合物的方法以及含有该化合物的药物组合物。
• [EN] BENZIMIDAZOLES AND RELATED ANALOGS AS SIRTUIN MODULATORS<br/>[FR] BENZIMIDAZOLES ET ANALOGUES ASSOCIÉS EN TANT QUE MODULATEURS DE SIRTUINE
  申请人：SIRTRIS PHARMACEUTICALS INC

  公开号：WO2010003048A1

  公开（公告）日：2010-01-07

  Provided herein are sirtuin-modulating compounds of formula (II) The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

  本文提供了公式（II）的调节sirtuin的化合物。这些调节sirtuin的化合物可用于延长细胞的寿命，并用于治疗和/或预防各种疾病和紊乱，包括与衰老或压力有关的疾病或紊乱、糖尿病、肥胖、神经退行性疾病、心血管疾病、血液凝块紊乱、炎症、癌症、潮红以及那些会受益于增加线粒体活性的疾病或紊乱。还提供了包含调节sirtuin化合物与另一治疗剂结合的组合物。
• Origins of Initiation Rate Differences in Ruthenium Olefin Metathesis Catalysts Containing Chelating Benzylidenes
  作者：Keary M. Engle、Gang Lu、Shao-Xiong Lennon Luo、Lawrence M. Henling、Michael K. Takase、Peng Liu、K. N. Houk、Robert H. Grubbs

  DOI：10.1021/jacs.5b01144

  日期：2015.5.6

  A series of second-generation ruthenium olefin metathesis catalysts was investigated using a combination of reaction kinetics, X-ray crystallography, NMR spectroscopy, and DFT calculations in order to determine the relationship between the structure of the chelating o-alkoxybenzylidene and the observed initiation rate. Included in this series were previously reported catalysts containing a variety

  结合反应动力学、X 射线晶体学、核磁共振光谱和 DFT 计算，研究了一系列第二代钌烯烃复分解催化剂，以确定螯合邻烷氧基亚苄基的结构与观察到的引发率之间的关系. 该系列包括先前报道的含有多种亚苄基改性的催化剂以及四种含有环丙氧基、新戊氧基、1-金刚烷氧基和2-金刚烷氧基的新型催化剂。这一系列催化剂的引发速率是使用 UV/vis 测定法确定的。观察到所有四种新催化剂都比相应的异丙氧基对照物更快引发，并且发现 2-金刚烷氧基催化剂是迄今为止报道的引发最快的 Hoveyda 型催化剂之一。对这些催化剂的 X 射线晶体结构和计算出的能量最小化结构的分析表明，Ru-O 键长和 Ru-O 键强度之间没有相关性。另一方面，发现引发速率与计算的 Ru-O 键强度密切相关。后一个发现通过计算单个热力学参数使催化剂引发的合理化和预测成为可能，其中没有对引发步骤的机制进行假设。
• 2,3-DIHYDROBENZO(<i>f</i>)-l,4-OXATHIEPIN AND DERIVATIVES
  作者：Marshall Kulka

  DOI：10.1139/v55-173

  日期：1955.9.1

  A method has been developed for the synthesis of a new heterocyclic system III. When 2-β-chloroethoxybenzyl chloride (XI) was heated with thiourea in alcohol solution, S-(2-β-chloroethoxybenzyl)isothiuronium chloride (XII) was formed which on cleavage with aqueous alkali in high dilution yielded 2,3-dihydrobenzo(f)-1,4-oxathiepin (III). Derivatives of III with substituents such as methyl, t-butyl, chlorine, and nitro in the 7 and 9 positions were prepared in high yields from the corresponding substituted 2-β-chloroethoxybenzyl chlorides. The presence of substituents in the position ortho to the chloroethoxy group of XII had no retarding effect on the cyclization to XIV.

  已开发出一种合成新杂环系统 III 的方法。当 2-β-氯乙氧基苄氯（XI）在醇溶液中与硫脲加热时，形成了 S-(2-β-氯乙氧基苄)异硫脲盐酸盐（XII），在高稀释条件下与水性碱裂解，生成了2,3-二氢苯并(f)-1,4-噁硫杂环（III）。通过对应的取代的 2-β-氯乙氧基苄氯制备了 III 的衍生物，这些衍生物在 7 和 9 位置带有甲基、叔丁基、氯和硝基等取代基，并且产率很高。XII 的氯乙氧基基团正交位上的取代基对生成 XIV 的环化反应没有延缓作用。