6-羟基-1,4-苯并二恶烷6-乙酸酯 | 7159-14-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 中文名称: 6-羟基-1,4-苯并二恶烷6-乙酸酯
• 英文名称: 2,3-dihydro-1,4-benzodioxin-6-yl acetate
• 英文别名: 6-Acetoxy-2,3-dihydro-benzo[1,4]dioxin；2,3-dihydrobenzo[b][1,4]dioxin-6-yl acetate
• CAS: 7159-14-0
• 化学式: C₁₀H₁₀O₄
• mdl: MFCD27927845
• 分子量: 194.187
• InChiKey: VUFRIRUMGMOOJQ-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111 °C
• 沸点：
  150-152 °C(Press: 6 Torr)
• 密度：
  1.244±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、可溶于二氯甲烷、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-羟基-1,4-苯并二恶烷6-乙酸酯 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 sodium iodide 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 丙酮 为溶剂， 反应 13.5h， 生成 hydroxy-6 benzodioxinne-1,4
  参考文献：
  名称：

  Synthèse et propriétés biologiques photoinduites de dioxinnocoumarines linéaires

  摘要：

  DOI：

  10.1016/0223-5234(90)90163-w
• 作为产物：
  描述：

  6-氨基-1,4-苯并二氧杂环 在 sodium hydroxide 、 硫酸 、 sodium nitrite 作用下， 反应 3.0h， 生成 6-羟基-1,4-苯并二恶烷6-乙酸酯
  参考文献：
  名称：

  Synthèse et propriétés biologiques photoinduites de dioxinnocoumarines linéaires

  摘要：

  DOI：

  10.1016/0223-5234(90)90163-w

文献信息

• Vanilloid receptor ligands and their use in treatments
  申请人：Wang Hui-Ling

  公开号：US20050176726A1

  公开（公告）日：2005-08-11

  Pyrimidine ethers and compositions containing them, for the treatment of acute, inflammatory and neuropathic pain, dental pain, general headache, migraine, cluster headache, mixed-vascular and non-vascular syndromes, tension headache, general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, inflammatory pain and associated hyperalgesia and allodynia, neuropathic pain and associated hyperalgesia and allodynia, diabetic neuropathy pain, causalgia, sympathetically maintained pain, deafferentation syndromes, asthma, epithelial tissue damage or dysfunction, herpes simplex, disturbances of visceral motility at respiratory, genitourinary, gastrointestinal or vascular regions, wounds, burns, allergic skin reactions, pruritus, vitiligo, general gastrointestinal disorders, gastric ulceration, duodenal ulcers, diarrhea, gastric lesions induced by necrotising agents, hair growth, vasomotor or allergic rhinitis, bronchial disorders or bladder disorders.

  嘌呤醚及含有它们的组合物，用于治疗急性、炎症性和神经痛、牙痛、普通头痛、偏头痛、集群头痛、混合血管和非血管综合症、紧张性头痛、一般炎症、关节炎、风湿病、骨关节炎、炎症性肠道疾病、炎症性眼部疾病、炎症性或不稳定的膀胱疾病、牛皮癣、伴有炎症成分的皮肤问题、慢性炎症症状、炎症性疼痛及相关的过敏性疼痛和触痛、神经痛及相关的过敏性疼痛和触痛、糖尿病性神经病痛、烧灼性疼痛、交感神经维持性疼痛、感觉缺失综合症、哮喘、上皮组织损伤或功能障碍、单纯疱疹、呼吸、泌尿生殖、胃肠或血管区域内脏运动障碍、伤口、烧伤、过敏性皮肤反应、瘙痒、白癜风、一般胃肠道紊乱、胃溃疡、十二指肠溃疡、腹泻、由坏死剂引起的胃损伤、毛发生长、血管运动性或过敏性鼻炎、支气管疾病或膀胱疾病。
• Substituted heterocyclic compounds, method for preparing and compositions containing same
  申请人：Adir et Compagnie

  公开号：US06313160B1

  公开（公告）日：2001-11-06

  The invention relates to compounds of formula (I): wherein: R1, R2 and R3 are as defined in the description, X is as defined in the description, Y represents an oxygen atom, a sulphur atom, a C(H)q group, SO or SO2, n is equal to from 0 to 5, A represents a NR5R6 group, and medicinal products containing the same which are useful in treating or in preventing melatoninergic disorders.

  该发明涉及以下式（I）的化合物：其中：R1、R2和R3如描述中定义，X如描述中定义，Y代表氧原子、硫原子、C（H）q基团、SO或SO2，n等于0至5，A代表NR5R6基团，以及含有这些化合物的药物产品，可用于治疗或预防褪黑素失调疾病。
• [EN] PYRIMIDINE DERIVATIVES FOR USE AS VANILLOID RECEPTOR LIGANDS AND THEIR USE IN THE TREATMENT OF PAIN<br/>[FR] DERIVES DE PYRIMIDINE UTILISES COMME LIGANDS DE RECEPTEUR DE VANILLOIDE ET LEUR UTILISATION DANS LE TRAITEMENT DE LA DOULEUR
  申请人：AMGEN INC

  公开号：WO2005077944A1

  公开（公告）日：2005-08-25

  Pyrimidine ethers and compositions containing them, fo use as vanilloid receptor ligands for the treatment of acute, inflammatory and neuropathic pain, dental pain, general headache, migraine, cluster headache, mixed-vascular and non-vascular syndromes, tension headache, general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, inflammatory pain and associated hyperalgesia and allodynia, neuropathic pain and associated hyperalgesia and allodynia, diabetic neuropathy pain, causalgia, sympathetically maintained pain, deafferentation syndromes, asthma, epithelial tissue damage or dysfunction, herpes simplex, disturbances of visceral motility at respiratory, genitourinary, gastrointestinal or vascular regions, wounds, burns, allergic skin reactions, pruritus, vitiligo, general gastrointestinal disorders, gastric ulceration, duodenal ulcers, diarrhea, gastric lesions induced by necrotising agents, hair growth, vasomotor or allergic rhinitis, bronchial disorders or bladder disorders. Wherein R1 - R4 and X are as defined in the claims.

  含有嘧啶醚化合物的组合物，用作vanilloid受体配体，用于治疗急性、炎症性和神经病理性疼痛、牙痛、普通头痛、偏头痛、群集性头痛、混合血管和非血管综合症、紧张性头痛、一般炎症、关节炎、风湿病、骨关节炎、炎症性肠病、炎症性眼病、炎症性或不稳定膀胱疾病、牛皮癣、具有炎症成分的皮肤疾病、慢性炎症状态、炎症性疼痛及相关的高敏性和触痛、神经病理性疼痛及相关的高敏性和触痛、糖尿病性神经病疼痛、交感神经维持的疼痛、去神经症候群、哮喘、上皮组织损伤或功能障碍、单纯疱疹、呼吸、泌尿、胃肠或血管区域内脏运动障碍、创伤、烧伤、过敏性皮肤反应、瘙痒、白癜风、一般胃肠道疾病、胃溃疡、十二指肠溃疡、腹泻、坏死性剂引起的胃病变、毛发生长、血管运动性或过敏性鼻炎、支气管疾病或膀胱疾病。其中R1-R4和X的定义如权利要求中所述。
• Substituted heterocyclic compounds
  申请人：ADIR ET COMPAGNIE

  公开号：US20020052400A1

  公开（公告）日：2002-05-02

  The invention relates to compounds of formula (I): 1 wherein: R 1 , R 2 and R 3 are as defined in the description, X is as defined in the description, Y represents an oxygen atom, a sulphur atom, a C(H)q group, SO or S0 2 , n is equal to from 0 to 5, A represents a NR 5 R 6 or CZNR 8 R 9 group. and medicinal products containing the same are useful in treating or in preventing melatoninergic disorders.

  本发明涉及式(I)的化合物：其中：R1、R2和R3如描述中所定义，X如描述中所定义，Y代表氧原子、硫原子、C(H)q基团、SO或S02，n等于0到5，A代表NR5R6或CZNR8R9基团。含有该化合物的药物在治疗或预防褪黑素失调方面具有有用性。
• Discovery of Potent, Orally Available Vanilloid Receptor-1 Antagonists. Structure−Activity Relationship of <i>N</i>-Aryl Cinnamides
  作者：Elizabeth M. Doherty、Christopher Fotsch、Yunxin Bo、Partha P. Chakrabarti、Ning Chen、Narender Gavva、Nianhe Han、Michael G. Kelly、John Kincaid、Lana Klionsky、Qingyian Liu、Vassil I. Ognyanov、Rami Tamir、Xianghong Wang、Jiawang Zhu、Mark H. Norman、James J. S. Treanor

  DOI：10.1021/jm049485i

  日期：2005.1.1

  The vanilloid receptor-1 (TRPV1 or VR1) is a member of the transient receptor potential (TRP) family of ion channels and plays a role in regulating the function of sensory nerves. A growing body of evidence demonstrates the therapeutic potential of TRPV1 modulators: particularly in the management of pain. As a result of our screening efforts, we identified (E)-3-(4-tert-butylphenyl)-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylamide (1): an antagonist that blocks the capsaicin-induced and pH-induced uptake of Ca-45(2+) in TRPV1-expressing Chinese hamster ovary cells with IC50 values of 17 +/- 5 and 150 +/- 80 nM, respectively. In this report.. we describe the synthesis and structure-activity relationship of a series of N-aryl cinnamides, the most potent of which (49a and 49b) exhibit good oral bioavailability in rats (F-oral = 39% and 17%. respectively).