1-chloro-3-[3-(trifluoromethyl)phenoxy]-2-propanol | 35948-65-3

• 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-chloro-3-[3-(trifluoromethyl)phenoxy]-2-propanol
• 英文别名: 1-chloro-3-[3-(trifluoromethyl)phenoxy]propan-2-ol
• CAS: 35948-65-3
• 化学式: C₁₀H₁₀ClF₃O₂
• 分子量: 254.636
• InChiKey: ZCIYBUOFJPLMLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-chloro-3-[3-(trifluoromethyl)phenoxy]-2-propanol 在 吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 Benzyl-carbamic acid 1-chloromethyl-2-(3-trifluoromethyl-phenoxy)-ethyl ester
  参考文献：
  名称：

  Phytoene Desaturase Inhibition by O-(2-Phenoxy)ethyl-N-aralkylcarbamates

  摘要：

  O-[1-Ethyl-2-(3-trifluoromethylphenoxy)]ethyl-N-benzylcarbamate exhibits a marked inhibition of carotenoid biosynthesis. Forty-one analogues were synthesized and assayed for plant-type phytoene desaturase (PDS) and zeta-carotene desaturase (ZDS) inhibition in a cell-free system using recombinant enzymes obtained from Escherichia coli transformants. The target enzyme of all carbamates synthesized in this study is PDS and not ZDS; no inhibition of ZDS was observed using a 10(-4) M inhibitor concentration. Four compounds, O-[1-ethyl-2-(3-trifluoromethylphenoxy)]ethyl-N-(2-phenylethyl)carbamate (23), O-[1-ethyl-2-(3-trifluoromethylphenoxy)]ethyl-N-(2-chlorobenzyl)carbamate (25), O-[1-ethyl-2-(3-trifluoromethylphenoxy)]ethyl-N-(2-chlorobenzyl)carbamate (26), and a[1-methyl-2(3-trifluoromethylphenoxy)]ethyl-N-benzylcarbamate (30), were the most potent PDS inhibitors. Their p/(50) values, the negative logarithms of the molar concentration that produces a 50% inhibition, were 7.5, representing the same inhibitory activity as norflurazon. With respect to a structure-activity relationship the oxygen atom of the phenoxy group and a carbamate structure in O-(1-ethyl-2-phenoxy) ethyl-N-aralkylcarbamates studied were found to be essential for strong PDS inhibitors. Also, introduction of an ethyl group at the alpha-position of the ethylene bridge between the phenoxy group and the carbamate was important for a strong PDS inhibitor. Substituents at the 2- and/or 3-position of the phenoxybenzene ring were found to be favorable to a strong PDS inhibition of the analogues.

  DOI：

  10.1021/jf0262413
• 作为产物：
  描述：

  间三氟甲基苯酚 、 环氧氯丙烷 、 potassium carbonate 在 环氧氯丙烷 、 水 、 二氯甲烷 、 盐酸 、 Sodium sulfate-III 作用下， 反应 2.5h， 以to give 76.2 g of crude 1-chloro-3-[3-(trifluoromethyl)phenoxy]-2-propanol which的产率得到1-chloro-3-[3-(trifluoromethyl)phenoxy]-2-propanol
  参考文献：
  名称：

  Process for the preparation of prostaglandin derivatives

  摘要：

  本发明提供了一种制备前列腺素及其类似物的新工艺，以及该工艺中的新晶体中间体。

  公开号：

  US20050209337A1

文献信息

• .beta.-Adrenergic blocking agents. V. 1-Amino-3-(substituted phenoxy)-2-propanols
  作者：Albert F. Crowther、D. J. Gilman、B. J. McLoughlin、Leslie Harold Smith、R. W. Turner、T. M. Wood

  DOI：10.1021/jm00304a018

  日期：1969.7
• US7166730B2
  申请人：——

  公开号：US7166730B2

  公开（公告）日：2007-01-23
• Phytoene Desaturase Inhibition by <i>O</i>-(2-Phenoxy)ethyl-<i>N</i>-aralkylcarbamates
  作者：Shinpei Ohki、Roswitha Miller-Sulger、Ko Wakabayashi、Wolfgang Pfleiderer、Peter Böger

  DOI：10.1021/jf0262413

  日期：2003.5.1

  O-[1-Ethyl-2-(3-trifluoromethylphenoxy)]ethyl-N-benzylcarbamate exhibits a marked inhibition of carotenoid biosynthesis. Forty-one analogues were synthesized and assayed for plant-type phytoene desaturase (PDS) and zeta-carotene desaturase (ZDS) inhibition in a cell-free system using recombinant enzymes obtained from Escherichia coli transformants. The target enzyme of all carbamates synthesized in this study is PDS and not ZDS; no inhibition of ZDS was observed using a 10(-4) M inhibitor concentration. Four compounds, O-[1-ethyl-2-(3-trifluoromethylphenoxy)]ethyl-N-(2-phenylethyl)carbamate (23), O-[1-ethyl-2-(3-trifluoromethylphenoxy)]ethyl-N-(2-chlorobenzyl)carbamate (25), O-[1-ethyl-2-(3-trifluoromethylphenoxy)]ethyl-N-(2-chlorobenzyl)carbamate (26), and a[1-methyl-2(3-trifluoromethylphenoxy)]ethyl-N-benzylcarbamate (30), were the most potent PDS inhibitors. Their p/(50) values, the negative logarithms of the molar concentration that produces a 50% inhibition, were 7.5, representing the same inhibitory activity as norflurazon. With respect to a structure-activity relationship the oxygen atom of the phenoxy group and a carbamate structure in O-(1-ethyl-2-phenoxy) ethyl-N-aralkylcarbamates studied were found to be essential for strong PDS inhibitors. Also, introduction of an ethyl group at the alpha-position of the ethylene bridge between the phenoxy group and the carbamate was important for a strong PDS inhibitor. Substituents at the 2- and/or 3-position of the phenoxybenzene ring were found to be favorable to a strong PDS inhibition of the analogues.
• Process for the preparation of prostaglandin derivatives
  申请人：Gutman Arie

  公开号：US20050209337A1

  公开（公告）日：2005-09-22

  The invention provides a novel process for the preparation of prostaglandins and analogues thereof, and new crystalline intermediates in the process.

  该发明提供了一种制备前列腺素及其类似物的新工艺，并在该过程中提供了新的晶体中间体。