4-(氯甲基)-1-甲氧基-2-苯基甲氧基苯 | 1699-38-3

• 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-(氯甲基)-1-甲氧基-2-苯基甲氧基苯
• 英文名称: 3-benzyloxy-4-methoxy-benzyl chloride
• 英文别名: 2-benzyloxy-4-chloromethyl-1-methoxy-benzene；α-Chlor-4-methoxy-3-benzyloxy-toluol；2-Benzyloxy-4-chlormethyl-1-methoxy-benzol；4-Methoxy-3-benzyloxy-benzylchlorid；3-benzyloxy-4-methoxybenzylchloride；2-(Benzyloxy)-4-(chloromethyl)-1-methoxybenzene；4-(chloromethyl)-1-methoxy-2-phenylmethoxybenzene
• CAS: 1699-38-3
• 化学式: C₁₅H₁₅ClO₂
• 分子量: 262.736
• InChiKey: WVWFKLUFYXQFHO-UHFFFAOYSA-N

物化性质

• 沸点：
  380.8±32.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(氯甲基)-1-甲氧基-2-苯基甲氧基苯 在 palladium 10% on activated carbon 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 甲苯 、 乙腈 为溶剂， 反应 27.0h， 生成 5-[2-(5,5-dioxo-10H-phenothiazin-1-yl)ethyl]-2-methoxyphenol
  参考文献：
  名称：

  Synthesis, antiproliferative activity and tubulin targeting effect of acridinone and dioxophenothiazine derivatives

  摘要：

  The synthesis of new acridinone and dioxophenothiazine derivatives along with their tubulin polymerization inhibitory and antiproliferative activities is reported. The analysis of correlation for cytotoxic and antitubulin potential of tested compounds showed that 4-methoxyphenylethyl derivatives 18a and 19a were highly cytotoxic but were regarded to have no significant antitubulin activity. However, the introduction of a 3-hydroxy substituent leading to compounds 18e and 19e, strongly increased the antitubulin potential but was associated with a loss of the antiproliferative activity. Modeling studies, topoisomerase inhibition assays and cell cycle analysis have been performed to better investigate the mechanism of action of such compounds. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.051
• 作为产物：
  描述：

  3-羟基-4-甲氧基苯甲醇 在 甲醇 、 氯化亚砜 、 sodium methylate 作用下， 生成 4-(氯甲基)-1-甲氧基-2-苯基甲氧基苯
  参考文献：
  名称：

  Zur Synthese der Homoisovanillinsäure

  摘要：

  DOI：

  10.1002/ardp.19392770606

文献信息

• Process for preparing fluorinated amino-nitriles
  申请人：Merrell Toraude et Compagnie

  公开号：US04405530A1

  公开（公告）日：1983-09-20

  Certain .alpha.-(fluoromethyl or difluoromethyl)-.alpha.-aminoacetonitriles are prepared by treating the appropriate .alpha.-(fluoromethyl or difluoromethyl) ketimine magnesium halide with hydrogen cyanide or with an alkali metal cyanide or ammonium cyanide and a proton source. The products are useful as intermediates for making .alpha.-(fluoromethyl or difluoromethyl)-.alpha.-amino acids having pharmacological activity.

  某些α-(氟甲基或二氟甲基)-α-氨基乙腈是通过将相应的α-(氟甲基或二氟甲基)酮亚胺镁卤化物与氢氰酸或与碱金属氰化物、氰化铵及质子源反应制备而成。这些产物作为中间体，可用于合成具有药理活性的α-(氟甲基或二氟甲基)-α-氨基酸。
• Design, Synthesis, Structure−Activity Relationships, and Biological Characterization of Novel Arylalkoxyphenylalkylamine σ Ligands as Potential Antipsychotic Drugs
  作者：Atsuro Nakazato、Kohmei Ohta、Yoshinori Sekiguchi、Shigeru Okuyama、Shigeyuki Chaki、Yutaka Kawashima、Katsuo Hatayama

  DOI：10.1021/jm980212v

  日期：1999.3.1

  sigma Receptor antagonists may be effective antipsychotic drugs that do not induce motor side effects caused by ingestion of classical drugs such as haloperidol. We obtained evidence that 1-(2-dipropylaminoethyl)-4-methoxy-6H-dibenzo[b,d]pyran hydrochloride 2a had selective affinity for sigma receptor over dopamine D2 receptor. This compound was designed to eliminate two bonds of apomorphine 1 to produce

  sigma受体拮抗剂可能是有效的抗精神病药物，不会引起因摄入氟哌啶醇等经典药物而引起的运动副作用。我们获得的证据表明，1-（2-二丙基氨基乙基）-4-甲氧基-6H-二苯并[b，d]吡喃盐酸盐2a对sigma受体的选择性亲和力高于多巴胺D2受体。设计该化合物可消除阿扑吗啡1的两个键，从而为氮原子产生结构柔性，并通过-CH2O-键桥接两个苯环，以维持平面结构。根据证据，设计了N，N-二丙基-2-（4-甲氧基-3-苄氧基苯基）乙胺盐酸盐10b。由于化合物10b消除了6H-二苯并[b，d]吡喃衍生物2a的联苯键，因此与化合物2a相比，它可能从阿扑吗啡1的刚性结构中释放出来。化合物10b的化学修饰导致人们发现，N，N-二丙基-2- [4-甲氧基-3-（2-苯基乙氧基）苯基]乙胺盐酸盐10g（NE-100）是芳基烷氧基苯基烷基胺衍生物3中最好的化合物，口服该药物对sigma受体具有很高的选择性亲和力，
• Method of depleting endogenous monoamines
  申请人：Merrell-Toraude et Cie

  公开号：US04342780A1

  公开（公告）日：1982-08-03

  2-Amino-2-fluoromethyl-3-(substituted)phenyl propionic acids and derivatives thereof are coadministered with dopamine for the treatment of schizophrenia, mania, tardive dyskinesia, anxiety, or depression.

  2-氨基-2-氟甲基-3-(取代)苯基丙酸及其衍生物与多巴胺联合使用，用于治疗精神分裂症、躁狂症、迟发性运动障碍、焦虑症或抑郁症。
• Unusual methyl transfer in the biosynthesis of aporphine and protoberberine alkaloids
  作者：Bernd Schneider、Meinhart H. Zenk

  DOI：10.1016/0031-9422(93)85226-h

  日期：1993.3

  Abstract ( S )-Reticuline was triply-labelled with 13 C and administered to cell cultures of Peumus boldus and Berberis stolonifera , which are sour

  摘要 ( S )-网状番荔枝碱用 13 C 进行三重标记，并施用于 Peumus boldus 和 Berberis stolonifera 的细胞培养物，它们是酸的
• Designing New Analogs for Streamlining the Structure of Cytotoxic Lamellarin Natural Products
  作者：Kassrin Tangdenpaisal、Rattana Worayuthakarn、Supatra Karnkla、Poonsakdi Ploypradith、Pakamas Intachote、Suchada Sengsai、Busakorn Saimanee、Somsak Ruchirawat、Montakarn Chittchang

  DOI：10.1002/asia.201403361

  日期：2015.4

  Despite the therapeutic potential of marine‐derived lamellarin natural products, their preclinical development has been hampered by their lipophilic nature, causing very poor aqueous solubility. In order to develop more drug‐like analogs, their structure was streamlined in this study from both the cytotoxic activity and lipophilicity standpoints. First, a modified total synthetic route was successfully

  尽管海洋来源的lamellarin天然产物具有治疗潜力，但其亲脂性质阻碍了它们的临床前开发，导致水溶性很差。为了开发更多类似药物的类似物，本研究从细胞毒性活性和亲脂性的角度简化了它们的结构。首先，成功设计了一条改良的总合成路线来构建59个系统设计的lamellarin类似物的文库，然后对其进行细胞毒性和log P测定。连同先前在我们实验室中合成的25种第一代薄片蛋白，对结构-活性和结构-亲脂性之间的关系进行了广泛的评估。我们的结果清楚地表明了层状蛋白骨架周围的其他结构要求，

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