1-<(4-fluorobenzhydryl)oxy>-2-chloroethane | 1494-72-0

• 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-<(4-fluorobenzhydryl)oxy>-2-chloroethane
• 英文别名: 1-[(4-fluorophenyl)phenylmethoxy]-2-chloroethane；2-Chloroethyl-4'-fluorobenzhydryl ether；1-[(2-chloro-ethoxy)-phenyl-methyl]-4-fluoro-benzene；2-[(4-fluorophenyl)-phenylmethoxy]ethyl chloride；2-Chlorethyl-p-fluorbenzhydrylether；1-[2-Chloroethoxy(phenyl)methyl]-4-fluorobenzene
• CAS: 1494-72-0
• 化学式: C₁₅H₁₄ClFO
• 分子量: 264.727
• InChiKey: OSRVRGRPZGMZAO-UHFFFAOYSA-N

物化性质

• 沸点：
  154 °C(Press: 2 Torr)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 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：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-<(4-fluorobenzhydryl)oxy>-2-chloroethane 在 盐酸 、 sodium carbonate 、 sodium iodide 作用下， 以 乙醇 、 水 、 丁酮 为溶剂， 反应 49.5h， 生成 1-[2-[(4-fluorophenyl)phenylmethoxy]ethyl]-4-(3-phenylpropyl)piperazine dihydrochloride
  参考文献：
  名称：

  Scale-Up Synthesis of the Dopamine Uptake Inhibitor GBR-12909

  摘要：

  1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (GBR-12909) is a dopamine uptake inhibitor. The development of a robust process for the preparation of this compound in kilogram quantities is described. The primary aims of the development work were to eliminate chromatographic purifications, to minimize the use of environmentally unacceptable reagents, and to improve the overall yield of the three-step convergent process. These objectives were met, with significant improvements obtained in the key coupling reaction of N-(3-phenylpropyl)piperazine dihydrochloride salt with 1-[bis(4-fluorophenyl)methoxy]-2-chloroethane, which was previously low-yielding and lacking in reproducibility.

  DOI：

  10.1021/op020211j
• 作为产物：
  描述：

  4-氟二苯甲酮 在 sodium tetrahydroborate 、 硫酸 作用下， 以 正庚烷 、 二氯甲烷 、 异丙醇 为溶剂， 反应 22.5h， 生成 1-<(4-fluorobenzhydryl)oxy>-2-chloroethane
  参考文献：
  名称：

  Scale-Up Synthesis of the Dopamine Uptake Inhibitor GBR-12909

  摘要：

  1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (GBR-12909) is a dopamine uptake inhibitor. The development of a robust process for the preparation of this compound in kilogram quantities is described. The primary aims of the development work were to eliminate chromatographic purifications, to minimize the use of environmentally unacceptable reagents, and to improve the overall yield of the three-step convergent process. These objectives were met, with significant improvements obtained in the key coupling reaction of N-(3-phenylpropyl)piperazine dihydrochloride salt with 1-[bis(4-fluorophenyl)methoxy]-2-chloroethane, which was previously low-yielding and lacking in reproducibility.

  DOI：

  10.1021/op020211j

文献信息

• Synthesis and psychoanaleptic properties of new compounds structurally related to diphenhydramine
  作者：Andre Buzas、Andre Champagnac、Andre Dehnel、Gilbert Lavielle、Michele Pommier

  DOI：10.1021/jm00176a009

  日期：1980.2

  A new series of benzhydryloxyalkylpiperazines carrying a trivalent function has been synthesized and studied for its effects on the central nervous system. Most of the compounds exhibit unexpected nonamphetaminic psychoanaleptic properties. The structure-activity studies revealed the importance of the nature and the position of the substituents on the phenyl rings. However, no significant correlation

  合成了一系列具有三价功能的新的苯甲酰氧基烷基哌嗪，并研究了其对中枢神经系统的影响。大多数化合物表现出出乎意料的非麻醉性精神麻醉药特性。结构活性研究揭示了苯环上取代基的性质和位置的重要性。但是，没有观察到促萎缩或抗组胺作用与精神疗法特性之间的显着相关性。
• 1,4-disubstituted piperazines, pharmaceutical compositions thereof and
  申请人：Richter Gedeon Vegyeszeti Gyar

  公开号：US04866062A1

  公开（公告）日：1989-09-12

  The invention relates to novel 1,4-disubstituted piperazine derivatives of the general formula (I), pharmaceutically acceptable acid addition salts thereof, pharmaceutical compositions containing them and a process for their preparation. In the general formula (I) ##STR1## R.sub.1 and R.sub.2 are the same or different and stand for hydrogen or halogen or a lower alkyl, trihalomethyl or lower alkoxy group. The compounds of the general formula (I) are therapeutically useful for the treatment of diseases arising from a hypofunction of the dopaminergic system.

  本发明涉及新型1,4-二取代哌嗪衍生物的通式（I），其药学上可接受的酸加盐，含有它们的制药组合物以及它们的制备方法。在通式（I）中，R.sub.1和R.sub.2相同或不同，代表氢或卤素或较低的烷基，三卤甲基或较低的烷氧基。通式（I）化合物在治疗起因于多巴胺能系统低功能的疾病方面具有治疗作用。
• Van Der Zee; Koger; Gootjes, European Journal of Medicinal Chemistry, 1980, vol. 15, # 4, p. 363 - 370
  作者：Van Der Zee、Koger、Gootjes、Hespe

  DOI：——

  日期：——
• Saxena, Anil K.; Dhaon, Madhup K.; Ram, Siya, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 12, p. 1224 - 1232
  作者：Saxena, Anil K.、Dhaon, Madhup K.、Ram, Siya、Saxena, Mridula、Jain, Padam C.、et al.

  DOI：——

  日期：——
• Syntheses of Organic Fluorine Compounds. V. : Syntheses and Pharmacological Study of Quaternary Ammonium Salts of Fluorine-substituted Benzhydryl Aminoethyl Ethers
  作者：HIDEOMI FUKUDA、KAZUO WATANABE、NOBUKO NAKAMURA、CHIZUKO HOSHINO、KOJI MIZUKAMI、KICHITARO TAKATORI

  DOI：10.1248/yakushi1947.89.3_354

  日期：——