4-acetyl-2-((E)-2-phenylethenyl)oxazole | 364608-80-0

• 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: 4-acetyl-2-((E)-2-phenylethenyl)oxazole
• 英文别名: 1-[2-[(E)-2-phenylethenyl]-1,3-oxazol-4-yl]ethanone
• CAS: 364608-80-0
• 化学式: C₁₃H₁₁NO₂
• 分子量: 213.236
• InChiKey: DJRBYXGKZHBRBZ-BQYQJAHWSA-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：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-acetyl-2-((E)-2-phenylethenyl)oxazole 在 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-[(3S,5S)-3-hydroxy-5-(p-methoxybenzyloxy)-7-octenoyl]-2-((E)-2-phenylethenyl)oxazole
  参考文献：
  名称：

  Total synthesis of (−)-hennoxazole A

  摘要：

  The antiviral marine natural product (-)-hennoxazole A was efficiently synthesized by a convergent approach. The stereoselective synthesis of the functionalized tetrahydropyran fragment was accomplished by the Mukaiyama aldol reaction, chelation-controlled 1,3-syn reduction, Wacker oxidation, and acid catalyzed intramolecular ketalization. The nonconjugated triene fragment was synthesized by S(N)2 displacement of an allylic bromide with vinyllithium and the CrCl2-mediated iodoolefination followed by palladium-catalyzed cross coupling with MeMgBr. The final steps include the fragment coupling using DEPC and oxazole synthesis via an oxidation/cyclodehydration process. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00593-2
• 作为产物：
  描述：

  methyl 2-[(E)-2-phenylethenyl]-1,3-oxazole-4-carboxylate 在 三甲基铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 42.25h， 生成 4-acetyl-2-((E)-2-phenylethenyl)oxazole
  参考文献：
  名称：

  Total synthesis of (−)-hennoxazole A

  摘要：

  The antiviral marine natural product (-)-hennoxazole A was efficiently synthesized by a convergent approach. The stereoselective synthesis of the functionalized tetrahydropyran fragment was accomplished by the Mukaiyama aldol reaction, chelation-controlled 1,3-syn reduction, Wacker oxidation, and acid catalyzed intramolecular ketalization. The nonconjugated triene fragment was synthesized by S(N)2 displacement of an allylic bromide with vinyllithium and the CrCl2-mediated iodoolefination followed by palladium-catalyzed cross coupling with MeMgBr. The final steps include the fragment coupling using DEPC and oxazole synthesis via an oxidation/cyclodehydration process. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00593-2

文献信息

• Diamine Derivatives
  申请人：Ohta Toshiharu

  公开号：US20110312990A1

  公开（公告）日：2011-12-22

  A compound represented by the general formula (1): -Q 1 -Q 2 -T 0 -N(R 1 )-Q 3 -N(R 2 )-T 1 -Q 4 (1) wherein R 1 and R 2 are hydrogen atoms or the like; Q 1 is a saturated or unsaturated, 5- or 6-membered cyclic hydrocarbon group which may be substituted, or the like; Q 2 is a single bond or the like; Q 3 is a group in which Q 5 is an alkylene group having 1 to 8 carbon atoms, or the like; and T 0 and T 1 are carbonyl groups or the like; a salt thereof, a solvate thereof, or an N-oxide thereof. The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.

  化合物的一般式表示为(1)：-Q1-Q2-T0-N(R1)-Q3-N(R2)-T1-Q4(1)，其中R1和R2为氢原子或类似物；Q1为饱和或不饱和的5-或6-成员环烃基，可以是取代基或类似物；Q2为单键或类似物；Q3为其中Q5为1至8个碳原子的烷基或类似物的基团；T0和T1为羰基或类似物。该化合物及其盐、溶剂化物或N-氧化物可用于预防和/或治疗脑梗死、脑栓塞、心肌梗死、心绞痛、肺梗死、肺栓塞、布尔格病、深静脉血栓形成、弥散性血管内凝血综合征、瓣膜或关节置换后的血栓形成、血管成形术后的血栓形成和再闭塞、全身性炎症反应综合征(SIRS)、多器官功能障碍综合征(MODS)、体外循环期间的血栓形成或采血时的血液凝固。
• Total synthesis of (−)-hennoxazole A
  作者：Fumiaki Yokokawa、Toshinobu Asano、Takayuki Shioiri

  DOI：10.1016/s0040-4020(01)00593-2

  日期：2001.7

  The antiviral marine natural product (-)-hennoxazole A was efficiently synthesized by a convergent approach. The stereoselective synthesis of the functionalized tetrahydropyran fragment was accomplished by the Mukaiyama aldol reaction, chelation-controlled 1,3-syn reduction, Wacker oxidation, and acid catalyzed intramolecular ketalization. The nonconjugated triene fragment was synthesized by S(N)2 displacement of an allylic bromide with vinyllithium and the CrCl2-mediated iodoolefination followed by palladium-catalyzed cross coupling with MeMgBr. The final steps include the fragment coupling using DEPC and oxazole synthesis via an oxidation/cyclodehydration process. (C) 2001 Elsevier Science Ltd. All rights reserved.