1-chloromethyl 3-phenylpropyl ether | 90875-79-9

• 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: 1-chloromethyl 3-phenylpropyl ether
• 英文别名: chloromethyl 3-phenylpropyl ether；chloromethyl-(3-phenyl-propyl)-ether；Chlormethyl-(γ-phenyl-propyl)-aether；Chlormethyl-(3-phenyl-propyl)-aether；Chlormethyl-(3-phenyl-propyl)-ether；[3-(Chloromethoxy)propyl]benzene；3-(chloromethoxy)propylbenzene
• CAS: 90875-79-9
• 化学式: C₁₀H₁₃ClO
• 分子量: 184.666
• InChiKey: URONAYWODRPBTE-UHFFFAOYSA-N

物化性质

• 沸点：
  122.5-123.5 °C(Press: 9 Torr)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-chloromethyl 3-phenylpropyl ether 在 甲醇 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (1S,2R,5E,7R,8R,9R,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-6-(3-phenylpropoxymethoxy)-15-[4-(4-pyridin-3-ylimidazol-1-yl)butyl]-3,17-dioxa-15-azabicyclo[12.3.0]heptadec-5-ene-4,12,16-trione
  参考文献：
  名称：

  β-Keto-ester chemistry and ketolides. synthesis and antibacterial activity of 2-halogeno, 2-methyl and 2,3 enol-ether ketolides

  摘要：

  The effect of 2,3 modifications on the antibacterial activity of ketolides was evaluated by introducing substituents in position 2 and converting the C-1, C-2, C-3 beta-keto-ester into stable 2,3 enol-ether or 2,3 anhydro derivatives. Introduction of a fluorine in C-2. is beneficial with regard to the overall antibacterial spectrum whereas the enol-ether and 2,3 unsaturated compounds, as well as the bulky gem dimethyl or 2-chloro derivatives, are less active particularly against erythromycin resistant strains. A 2-fluoro ketolide derivative demonstrates good antibacterial activity and in vivo efficacy against multi-resistant Streptococcus pneumoniae. Compared to azithromycin against Haemophilus influenzae, this compound is equivalent in vitro and slightly more active in vivo. These results demonstrate that within the ketolide class, to retain good antibacterial activity, position needs to remain tetrahedral and tolerates only very small substituents such as fluorine. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00392-9
• 作为产物：
  描述：

  methylthiomethyl 3-phenylpropyl ether 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 1-chloromethyl 3-phenylpropyl ether
  参考文献：
  名称：

  Pyrimidinones as reversible metaphase arresting agents

  摘要：

  5-Halo-N(1)-substituted 2(1H)-pyrimidinones have the ability to cause reversible arrest of mitosis during metaphase, Highly active compounds have a heteroatom (O, S or N) in the beta-position of the N(1)-carbon chain which is further substituted by an aryl group. In vitro data have been provided. It is suggested that reversible metaphase inhibitors can be used as synchronizing agents of cell-cycles by applying them in a sequential manner when a phase-specific cytotoxic drug is used in the treatment of diseases caused by uncontrolled rapidly proliferating cells. The active compounds are prepared from 2-pyrimidinones by alkylation reactions. The key reactants are alpha-chloroalkyl ethers, sulfides and amides; methods for their syntheses have been described.

  DOI：

  10.1016/0223-5234(93)90014-6

文献信息

• Synthesis and Antimicrobial Activity of New Quaternary Ammonium Chlorides
  作者：Bogumil Brycki、Andrzej Skrzypczak、Ilona Mirska、Juliusz Pernak

  DOI：10.1002/ardp.19963290603

  日期：——

  ethers or sulfides, chloromethylbezyl ethers or sulfides and chloromethylcycloalkyl ethers to give quaternary ammonium chlorides in very good yields. All the chlorides studied showed antimicrobial activity. The relationship between the chemical structure and antimicrobial activity was analyzed by rough sets.

  癸基二甲胺很容易与氯甲基烷基醚或硫化物、氯甲基苄基醚或硫化物和氯甲基环烷基醚反应，以非常好的收率得到季铵氯化物。所研究的所有氯化物均显示出抗微生物活性。通过粗糙集分析化学结构与抗菌活性之间的关系。
• Antagonists of specific excitatory amino acid neurotransmitter receptors
  申请人：NOVA PHARMACEUTICAL CORPORATION

  公开号：EP0242709A2

  公开（公告）日：1987-10-28

  The invention pertains to novel, potent anticonvulsants, analgesics and cognition enhancers achieving their action through the antagonism of specific excitatory amino acid neurotransmitter receptors. In particular, the invention is directed to ω-[2-phosphonoalkylenyl)phenyl]-2-­aminoalkanoic acids having general formula: Wherein R₁ and R₂ are the same or different and are selected from the group consisting of hydrogen, lower alkyl, halogen, -CH=CH-CH=CH=, amino, nitro, trifluoromethyl or cyano; n and m = 0, 1, 2 or 3; and the pharmaceutically acceptable salts and derivatives thereof. Examples of specific preferred compounds of general formula are selected from the group consisting of: 4-[2-­phosphonomethylphenyl]-2-aminobutanoic acid, ethyl 3-[2-(2-­ (2-diethylphosphonoethyl)phenyl]-2-acetamido-2-­carboethoxypropanoate, 3-[2-phosphonomethyl)phenyl]-2-­aminopropanoic acid, ethyl 3-[2-(3-bromopropyl)phenyl]-2-­acetamido-3-carboethoxypropanoate, ethyl 3-[2-(3-­diethylphosphonopropyl)phenyl]-2-acetamido-2-­carboethoxypropanoate, ethyl 3-[2-(3-phosphonopropyl)-­phenyl]-2-aminopropanoic acid, ethyl 5-[2-­(diethylphosphonomethyl)-phenyl]-2- acetamido-2-­carboethoxypentanoate, and 5-[2-phosphonomethylphenyl]-2-­aminopentanoic acid. Furthermore, the invention relates to a process for preparing the said potent, selective excitatory amino acid neurotransmitter receptor antagonist.

  本发明涉及通过拮抗特定兴奋性氨基酸神经递质受体而发挥作用的新型强效抗惊厥药、镇痛药和认知增强剂。本发明尤其涉及通式为ω-[2-膦酰基烷烯基]苯基]-2-氨基烷酸： 其中，R₁ 和 R₂ 相同或不同，且选自由氢、低级烷基、卤素、-CH=CH-CH=CH=、氨基、硝基、三氟甲基或氰基组成的组；n 和 m = 0、1、2 或 3；及其药学上可接受的盐和衍生物。 具体优选的通式化合物的例子选自以下组成的组：4-[2-膦酰甲基苯基]-2-氨基丁酸、3-[2-(2-二乙基膦酰乙基)苯基]-2-乙酰氨基-2-羧乙氧基丙酸乙酯、3-[2-膦酰甲基)苯基]-2-氨基丙酸、3-[2-(3-溴丙基)苯基]-2-乙酰氨基-3-羧乙氧基丙酸乙酯、3-[2-(3-二乙基膦丙基)苯基]-2-乙酰氨基-2-羧乙氧基丙酸乙酯、3-[2-(3-膦丙基)-苯基]-2-氨基丙酸乙酯、5-[2-(二乙基膦甲基)-苯基]-2-乙酰氨基-2-羧乙氧基戊酸乙酯和 5-[2-膦甲基苯基]-2-氨基戊酸乙酯。此外，本发明还涉及一种制备上述强效、选择性兴奋性氨基酸神经递质受体拮抗剂的工艺。
• 9-(2-Aryloxyethyl) Derivatives of Adenine - a New Class of Non-nucleosidic Antiviral Agents
  作者：V. I. Petrov、A. A. Ozerov、M. S. Novikov、C. Pannecouque、J. Balzarini、E. De Clercq

  DOI：10.1023/b:cohc.0000008270.32235.2b

  日期：2003.9
• Sabetay; Schving, Bulletin de la Societe Chimique de France, 1928, vol. <4> 43, p. 1344
  作者：Sabetay、Schving

  DOI：——

  日期：——
• Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 3. Synthesis and evaluation of (alkenyloxy)-, (alkynyloxy)-, and (aralykyloxy)methyl quaternarized 2-[(hydroxyimino)methyl]-1-alkylimidazolium halides as reactivators and therapy for soman intoxication
  作者：Clifford D. Bedford、Ralph N. Harris、Robert A. Howd、Dane A. Goff、Gary A. Koolpe、M. Petesch、Irwin Koplovitz、Walter E. Sultan、H. A. Musallam

  DOI：10.1021/jm00122a035

  日期：1989.2

  A series of structurally related monosubstituted 1-[(alkenyloxy)methyl]-, 1-[(alkynyloxy)methyl]-, and 1-[(aralkyloxy)methyl]-2-[(hydroxyimino)methyl]-3-methyli midazolium halides were prepared and evaluated. All new compounds were characterized with respect to (hydroxyimino)methyl acid dissociation constant, nucleophilicity, and octanol-buffer partition coefficient. The alkynyloxy-substituted compounds were also evaluated in vitro with respect to reversible inhibition of human erythrocyte (RBC) acetylcholinesterase (AChE) and kinetics of reactivation of human AChE inhibited by ethyl p-nitrophenyl methylphosphonate (EPMP). In vivo evaluation in mice revealed that coadministration of alkynyloxy-substituted imidazolium compounds with atropine sulfate provided significant protection against a 2 x LD50 challenge of GD. For the alkynyloxy-substituted imidazolium drugs there is a direct relationship between in vitro and in vivo activity: the most potent in vivo compounds against GD proved to be potent in vitro reactivators against EPMP-inhibited human AChE. These results differ from the observations made on the sterically hindered imidazolium compounds (see previous article) and suggest that several antidotal mechanisms of protective action may be applicable for the imidazolium aldoxime family of therapeutics. The ability of the alkynyloxy substituents to provide life-saving protection against GD intoxication was not transferable to the pyridinium or triazolium heteroaromatic ring systems.