1,4-双(2-氯乙氧基)苯 | 37142-37-3

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 芳香烃
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1,4-双(2-氯乙氧基)苯
• 英文名称: 1,4-Bis(2-chloroethoxy)benzene
• 英文别名: p-bis(2-chloroethoxy)benzene；1,4-Bis-(β-chlorethoxy)-benzol
• CAS: 37142-37-3
• 化学式: C₁₀H₁₂Cl₂O₂
• mdl: MFCD00222550
• 分子量: 235.11
• InChiKey: DKPKDJGAQOVXJC-UHFFFAOYSA-N

物化性质

• 熔点：
  92-93°
• 沸点：
  121-124 °C(Press: 0.03 Torr)
• 密度：
  1.216±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮、氯仿、二氯甲烷、乙酸乙酯、四氢呋喃

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  1,4-双(2-氯乙氧基)苯 在 palladium on activated charcoal 正丁基锂 、 氢气 、 溴 、 四氯化锡 、 铁粉 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 29.25h， 生成 8-Methyl-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-4-carbaldehyde
  参考文献：
  名称：

  Dihydrobenzofuran Analogues of Hallucinogens. 3. Models of 4-Substituted (2,5-Dimethoxyphenyl)alkylamine Derivatives with Rigidified Methoxy Groups

  摘要：

  Tetrahydrobenzodifuran functionalities were employed as conformationally restricted bioisosteres of the aromatic methoxy groups in prototypical hallucinogenic phenylalkylamines 1 and 2. Thus, a series of 8-substituted 1-(2,3,6,7-tetrahydrobenzo[ 1,2-b:4,5-b']difuran-4-yl)-2-aminoalkanes (7a-e) were prepared and evaluated for activity in the two-lever drug discrimination paradigm in rats trained to discriminate saline from LSD tartrate (0.08 mg/kg) and for the ability to displace [H-3]ketanserin from rat cortical homogenate 5-HT2A receptors and [(3)H3-8-OH-DPAT from rat hippocampal homogenate 5-HT1A receptors. In addition, 1-(8-(bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5- (7b), which was found to be extremely potent in the rat in vivo assays, was evaluated for its ability to compete with [I-125][DOI and [H-3]ketanserin binding to cells expressing cloned human 5-HT2A, 5-H-2B, and 5-HT2C receptors. All of the dihydrofuranyl compounds having a hydrophobic substituent para to the alkylamine side chain had activities in both the in vitro and in vivo assays that equaled or surpassed the activity of the analogous conformationally flexible parent compounds. For example, 7b substituted for LSD in the drug discrimination assay with an ED(50) Of 61 nmol/kg and had K-i values in the nanomolar to subnanomolar range for the displacement of radioligand from rat and human 5-HT2 receptors, making it one of the most potent hallucinogen-like phenylalkylamine derivatives reported to date. The results suggest that the dihydrofuran rings in these pew analogues effectively model the active binding conformations of the methoxy groups of the parent compounds 1 and 2. In addition, the results provide information about the topography and relative orientation of residues involved in agonist binding in the serotonin 5-HT2 receptors.

  DOI：

  10.1021/jm960199j
• 作为产物：
  描述：

  对苯二酚二羟乙基醚 在 吡啶 、 氯化亚砜 作用下， 以88%的产率得到1,4-双(2-氯乙氧基)苯
  参考文献：
  名称：

  对映体的合成和一系列超强，构象受限的5-HT（2A / 2C）受体激动剂的药理学评价。

  摘要：

  配体对5-HT（2A）或5-HT（2C）激动剂结合位点的亲和力通过修饰典型的致幻性苯丙胺（如4b（DOB））中的2,5-氧取代基来增强。相对于母体2，5-二甲氧基化合物，构象柔性的2，5-二甲氧基取代基限制为稠合的二氢呋喃环通常导致效力增加。这些芳基烷基胺的纯对映体是通过对映体特异性合成得到的，该合成涉及用N-三氟乙酰基保护的D-或L-丙氨酰氯对杂环核7进行酰化，然后进行酮还原和N-脱保护。对映异构体在两个受体上显示适度的立体选择性。在它们的药理研究过程中，观察到了这些新化合物类别中的一些一般趋势。对于大多数测试的光学异构体对，在5-HT（2A）和5-HT（2C）受体上，含杂环7的化合物的R-对映体仅比其S-对映体具有更高的亲和力。同样，功能研究表明，与S-对映体相比，R-对映体通常显示出更高的效价。这些芳基烷基胺的二氢呋喃环的芳香化进一步增加了亲和力和效力。仅有少数化合物是完全激动剂，其

  DOI：

  10.1021/jm000491y

文献信息

• Synthesis and cytotoxic activity of novel tetrahydrobenzodifuran–imidazolium salt derivatives
  作者：Chao-Bo Zhang、Yang Liu、Zheng-Fen Liu、Sheng-Zu Duan、Min-Yan Li、Wen Chen、Yan Li、Hong-Bin Zhang、Xiao-Dong Yang

  DOI：10.1016/j.bmcl.2017.02.053

  日期：2017.4

  substituent or 2-naphthylacyl substituent, were important to the cytotoxic activity. Notably, 3-(2-Naphthylmethyl)-1-((2,3,6,7-tetrahydrobenzo[1,2-b;4,5-b']difuran-4-yl)methyl)-1H-5,6-dimethyl-benzimidazol-3-ium bromide (42) was found to be the most potent derivative against five human tumor cell lines with IC50 values of 1.06-4.34μM and more selective towards SMMC-7721, A549 and SW480 cell lines. 3-(2-Naphthylacyl)-1-((2

  提出了一系列新颖的4-取代的2,3,6,7-四氢苯并[1,2-b; 4,5-b']二呋喃-1H-咪唑鎓盐的合成。在体外针对一组人类肿瘤细胞系评估了化合物的生物学特性。结果表明5，6-二甲基苯并咪唑环或2-甲基苯并咪唑环以及用2-萘甲基取代基或2-萘甲酰基取代基取代咪唑基-3-位对于细胞毒性活性是重要的。值得注意的是，3-（2-萘基甲基）-1-（（（2,3,6,7-四氢苯并[1,2-b; 4,5-b']二呋喃-4-基）甲基）-1H-5，发现六甲基二甲基苯并咪唑-3-溴化铵（42）是针对五种人类肿瘤细胞系的最有效衍生物，IC50值为1.06-4.34μM，对SMMC-7721，A549和SW480细胞系更具选择性。3-（2-萘甲酰基）-1-（（（2,3,6,7-四氢苯并[1,2-b; 4，5-b']二呋喃-4-基）甲基）-1H-2-甲基苯并咪唑-3-溴化铵（37）对SMMC-7721和MCF-
• Synthesis of concave receptors derived from diphenylglycoluril
  作者：R. P. Sijbesma、R. J. M. Nolte

  DOI：10.1002/recl.19931121207

  日期：——

  Improved synthetic methods are described for the synthesis of concave receptor molecules. These receptors consist of a diphenylglycoluril unit, flanked by two aromatic moieties. The most versatile synthetic method consists of Lewis-acid-catalyzed reaction of a tetrakis(chloromethyl) derivative of diphenylglycoluril with the appropriate benzene or naphthalene derivative.

  描述了用于合成凹形受体分子的改进的合成方法。这些受体由二苯基甘氨酰脲单元构成，其两侧是两个芳族部分。最通用的合成方法包括路易斯酸催化的二苯基甘脲的四（氯甲基）衍生物与适当的苯或萘衍生物的反应。
• Synthesis of a new class of difunctional tetraphenylene crown ethers
  作者：Harry W Gibson、Devdatt S Nagvekar、Yadollah Delaviz、William S Bryant

  DOI：10.1139/v98-188

  日期：1998.10.1

  Three new substituted tetraphenylene crown ethers have been made. Bis(5-carbomethoxy-1,3-phenylene)-bis(p-phenylene)-(3x + 6)-crown-x, where x = 12, 16, and 20 (11b-11d) were synthesized via [1 + 1] cyclization of methyl 3,5-bis[omega-chloro(oligoethyleneoxy)]benzoates (13b-3d) with methyl 3,5-bis[omega-(p-hydroxyphenoxy)(oligoethyleneoxy)]benzoates (16b-6d) using K2CO3 as base and tetrabutylammonium

  已经制备了三种新的取代四亚苯基冠醚。双（5-碳甲氧基-1,3-亚苯基）-双（对-亚苯基）-(3x + 6)-冠-x，其中 x = 12、16 和 20 (11b-11d) 通过 [1 + 1] 3,5-双[ω-氯（低聚亚乙氧基）]苯甲酸甲酯（13b-3d）与3,5-双[ω-（对羟基苯氧基）（低聚亚乙氧基）]苯甲酸甲酯（16b-6d）环化K2CO3 作为碱和四丁基碘化铵作为二甲基甲酰胺 (DMF) 中的相转移剂。相应的 30 元 (x = 8) 大环 11a 不能通过这种方法制成；仅分离出消除产物 3,5-双（乙烯基氧基）苯甲酸 (19)。16a-16d 分别通过对苄氧基苯酚 (14) 与 13a-13d 的烷基化反应制备，然后用 Pd/C 作为催化剂进行氢解。
• Effect of the linker nature on the antibacterial activity of structural analogs of octenidine
  作者：I. K. Yakushchenko、N. N. Pozdeeva、A. A. Terentiev、S. Y. Gadomsky

  DOI：10.1007/s11172-022-3456-8

  日期：2022.3

  Four new octenidine analogs with different nature of the linkers between two N-octylpyridin-4-amines fragments were synthesized for the first time. The antibacterial activities of the synthesized compounds against Micrococcus luteus and Escherichia coli were studied by the method of serial dilutions using octenidine as the reference. A dependence of the antibacterial activity of the synthesized structural analogs of octenidine on the lipophilicity of dihalide used as a precursor of the linker was found: the higher the lipophilicity of the linker fragment, the lower the minimum inhibitory concentration of the compound.

  首次合成了四种新的辛烯啶类似物，其两个 N-辛基吡啶-4-胺片段之间的连接物具有不同的性质。以辛烯啶为参照物，通过系列稀释法研究了合成化合物对黄体微球菌和大肠杆菌的抗菌活性。研究发现，辛烯啶合成结构类似物的抗菌活性取决于作为连接体前体的二卤化物的亲油性：连接体片段的亲油性越高，化合物的最小抑菌浓度就越低。
• Novel substituted arylene compounds and processes for their production
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0032063A2

  公开（公告）日：1981-07-15

  Novel substituted arylene compounds and processes for their production are disclosed. These new compounds are useful as anti-arteriosclerotic agents. The novel compounds have the following formulae:- The radicals X,Y, Land M are each oxygen, sulfur, sulfone or sulfoxide and the other substituents are as defined at length in claim 1.

  本研究公开了新型取代芳烯化合物及其生产工艺。这些新化合物可用作抗动脉硬化剂。这些新型化合物的化学式如下 基团 X、Y、Land M 各为氧、硫、砜或亚砜，其他取代基如权利要求 1 详细定义的那样。