2-(2-n-hexylphenyl)-4,4-dimethyloxazoline | 136515-49-6

• 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: 2-(2-n-hexylphenyl)-4,4-dimethyloxazoline
• 英文别名: 2-(2-hexylphenyl)-4,4-dimethyl-5H-1,3-oxazole
• CAS: 136515-49-6
• 化学式: C₁₇H₂₅NO
• 分子量: 259.392
• InChiKey: ZLPHLHBSYGXKGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-n-hexylphenyl)-4,4-dimethyloxazoline 在 盐酸 、 sodium tetrahydroborate 作用下， 以 硝基甲烷 为溶剂， 反应 4.33h， 生成 2-Hexylbenzaldehyde
  参考文献：
  名称：

  作为强心剂的2-苯基噻唑烷衍生物的合成。I.2-苯基噻唑烷-3-硫代羧酰胺。

  摘要：

  一系列新型2-苯基噻唑烷-3-硫代氨基甲酸酯（II）被合成并测试了其在离体豚鼠心脏和麻醉犬中的正性肌力活性。苯甲醛（VI、XI、XIV和XV）与半胱胺反应后，再用异硫氰酸酯处理，即可得到II。通过改变结构参数来研究结构-活性关系。具有邻位取代基如Me或OMe的N-甲基-2-苯基噻唑烷-3-硫代氨基甲酸酯表现出显著的正性肌力作用，且该作用不受普萘洛尔阻断。在合成的各种邻位烷氧基苯基衍生物中，2-（2-（3-（4-苯基哌嗪）丙氧基）苯基）衍生物（I67）显示出比氨力农更强大且持久的活性，而对心率或血压无显著影响。

  DOI：

  10.1248/cpb.35.1953
• 作为产物：
  描述：

  正丁基锂 、 4,4-Dimethyl-2-(2-vinyl-phenyl)-4,5-dihydro-oxazole 以 乙醚 为溶剂， 反应 0.17h， 生成 2-(2-n-hexylphenyl)-4,4-dimethyloxazoline
  参考文献：
  名称：

  Tandem carbolithiation/cyclization of 2-(3-phenyl-2-propen-1-yl) oxazolines. A novel route to cyclobutane derivatives

  摘要：

  Reaction of the 2-(3-phenyl-2-propen-1-yl) oxazolines 1 and 3 with organolithium reagents leads to cyclobutane ring formation by a novel tandem carbolithiation/cyclization sequence. The products (e.g., 2a and 4a) may be hydrolyzed to the corresponding substituted cyclobutanones (e.g., 7 and 8). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10298-2

文献信息

• 5-Lipoxygenase inhibitors
  申请人：Eli Lilly and Company

  公开号：US05028629A1

  公开（公告）日：1991-07-02

  This invention relates to 2-(substituted)-N-hydroxy-N-alkylcinnamamides of the formula: ##STR1## where R.sup.1 is C.sub.1 -C.sub.4 alkyl; n is 0 or 1; R.sup.2 is trifuloromethyl, C.sub.1 -C.sub.10 alkyl, phen(C.sub.1 -C.sub.4)alkylene or ##STR2## where m is 0, 1 or 2 and R.sup.3 is C.sub.1 -C.sub.4 alkyl; X is C.sub.1 -C.sub.6 alkyl, phenyl, phen(C.sub.1 -C.sub.4)alkylene where the phenyl ring is unsubstituted or monosubstituted with --S(O).sub.m --R.sup.3 and m and R.sup.3 are as defined above, or ##STR3## where m is 0, 1 or 2 and R.sup.4 is C.sub.2 -C.sub.12 alkenyl, C.sub.2 -C.sub.12 alkynyl, or unsubstituted or monosubstituted C.sub.1 -C.sub.20 alkyl where the substituent is CF.sub.3, C.sub.3 -C.sub.8 cycloalkyl, or phenyl, or a pharmaceutically acceptable salt thereof; formulations containing those compounds and methods of using such compounds as 5-lipoxygenase inhibiting agents.

  这项发明涉及以下结构的2-(取代基)-N-羟基-N-烷基肉桂酰胺：##STR1##其中R.sup.1为C.sub.1 -C.sub.4烷基；n为0或1；R.sup.2为三氟甲基，C.sub.1 -C.sub.10烷基，苯(C.sub.1 -C.sub.4)烷基或##STR2##其中m为0, 1或2，R.sup.3为C.sub.1 -C.sub.4烷基；X为C.sub.1 -C.sub.6烷基，苯基，苯(C.sub.1 -C.sub.4)烷基，其中苯环未取代或单取代为--S(O).sub.m --R.sup.3，m和R.sup.3如上定义，或##STR3##其中m为0, 1或2，R.sup.4为C.sub.2 -C.sub.12烯基，C.sub.2 -C.sub.12炔基，或未取代或单取代的C.sub.1 -C.sub.20烷基，其中取代基为CF.sub.3，C.sub.3 -C.sub.8环烷基，或苯基，或其药学上可接受的盐；含有这些化合物的配方和使用这些化合物作为5-脂氧合酶抑制剂的方法。
• US5028629A
  申请人：——

  公开号：US5028629A

  公开（公告）日：1991-07-02
• Tandem carbolithiation/cyclization of 2-(3-phenyl-2-propen-1-yl) oxazolines. A novel route to cyclobutane derivatives
  作者：Ralph P. Robinson、Brian J. Cronin、Brian P. Jones

  DOI：10.1016/s0040-4039(97)10298-2

  日期：1997.12

  Reaction of the 2-(3-phenyl-2-propen-1-yl) oxazolines 1 and 3 with organolithium reagents leads to cyclobutane ring formation by a novel tandem carbolithiation/cyclization sequence. The products (e.g., 2a and 4a) may be hydrolyzed to the corresponding substituted cyclobutanones (e.g., 7 and 8). (C) 1997 Elsevier Science Ltd.
• Synthesis of 2-phenylthiazolidine derivatives as cardiotonic agents. I. 2-Phenylthiazolidine-3-thiocarboxamides.
  作者：HIROYUKI NATE、YASUO SEKINE、YASUSHI HONMA、HIDEO NAKAI、HIROSHI WADA、MIKIO TAKEDA、HIDEO YABANA、TAKU NAGAO

  DOI：10.1248/cpb.35.1953

  日期：——

  A series of novel 2-phenylthiazolidine-3-thiocarboxamides (II) was synthesized and tested for positive inotropic activity in the isolated guinea pig heart and in anesthetized dogs. Reaction of the benzaldehydes (VI, XI, XIV and XV) with cysteamine followed by treatment with isothiocyanates readily gave II. Structure-activity relationships were investigated by varying the structural parameters. N-Methyl-2 -phenylthiazolidine-3-thiocarboxamides having an ortho substituent such as a Me or OMe group exhibited significant positive inotropic action, which was not blocked by propranolol. Among the various ortho-alkoxyphenyl derivatives synthesized, the 2- (2- (3- (4-phenylpiperazino) propoxy) phenyl) derivative (I67) was found to exhibit more potent and longerlasting activity than amrinone without any significant effect on heart rate or blood pressure

  一系列新型2-苯基噻唑烷-3-硫代氨基甲酸酯（II）被合成并测试了其在离体豚鼠心脏和麻醉犬中的正性肌力活性。苯甲醛（VI、XI、XIV和XV）与半胱胺反应后，再用异硫氰酸酯处理，即可得到II。通过改变结构参数来研究结构-活性关系。具有邻位取代基如Me或OMe的N-甲基-2-苯基噻唑烷-3-硫代氨基甲酸酯表现出显著的正性肌力作用，且该作用不受普萘洛尔阻断。在合成的各种邻位烷氧基苯基衍生物中，2-（2-（3-（4-苯基哌嗪）丙氧基）苯基）衍生物（I67）显示出比氨力农更强大且持久的活性，而对心率或血压无显著影响。