2-chloro-5,7-bis(trifluoromethyl)-1H-benzoimidazole | 683240-87-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-chloro-5,7-bis(trifluoromethyl)-1H-benzoimidazole
• 英文别名: 2-chloro-4,6-bis(trifluoromethyl)-1H-benzo[d]imidazole；2-chloro-4,6-bis(trifluoromethyl)-1H-benzimidazole
• CAS: 683240-87-1
• 化学式: C₉H₃ClF₆N₂
• 分子量: 288.58
• InChiKey: FVPXNCMEKAXLNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  294.2±50.0 °C(Predicted)
• 密度：
  1.657±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-chloro-5,7-bis(trifluoromethyl)-1H-benzoimidazole 、 1-[3-(三氟甲基)吡啶-2-基]哌嗪 生成 4,6-bis(trifluoromethyl)-2-[4-(3-trifluoromethylpyridin-2-yl)piperazin-1-yl]-1H-benzoimidazole
  参考文献：
  名称：

  Vanilloid receptor ligands and their use in treatments

  摘要：

  具有以下一般结构的治疗性苯并咪唑类化合物和含有它们的组合物，用于治疗急性、炎症性和神经性疼痛、牙痛、普通头痛、偏头痛、集群性头痛、混合血管和非血管综合症、紧张性头痛、一般炎症、关节炎、风湿性疾病、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、具有炎症成分的皮肤疾病、慢性炎症状况、炎症性疼痛及相关的过敏性痛觉过敏和触觉过敏、神经性疼痛及相关的过敏性痛觉过敏和触觉过敏、糖尿病神经病性疼痛、烧伤后疼痛、交感神经维持疼痛、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、胃肠或血管区域的内脏运动障碍、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、血管运动或过敏性鼻炎、支气管疾病或膀胱疾病。

  公开号：

  US07582761B2
• 作为产物：
  描述：

  间二(三氟甲基)苯胺 在 硫酸 、 palladium 10% on activated carbon 、 水 、 氢气 、 硝酸 、 sodium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 25.0h， 生成 2-chloro-5,7-bis(trifluoromethyl)-1H-benzoimidazole
  参考文献：
  名称：

  Chiral 2-aminobenzimidazole bifunctional organocatalysts: effect of di-CF3 and TFA on catalytic mechanisms

  摘要：

  (S,S)-trans-Cyclohexanediamine-5,7-di-CF3-benzimidazole (3b) was developed as a new chiral bifunctional organocatalyst and successfully applied to Michael addition of diethyl malonate to nitroolefins (up to 99%, 98% ee) under neutral condition. Systematic investigation on the catalytic mechanism revealed that the role of the guanidine moiety and the dimethylamine moiety in catalysts might be reversed with respect to Bronsted/Lewis acidic or basic functionalities, depending on the reaction conditions (neutral or TFA co-catalyst). Generally, di-CF3 group substituted 2-aminobenzimidazole catalysts in neutral condition and non-substituted 2-aminobenzimidazole catalysts in co-catalyst (TFA) condition give high chemical yield and enantioselectivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.021

文献信息

• [EN] BENZIMIDAZOLE DERIVATIVES AND THEIR USE AS VANILLOID RECEPTOR LIGANDS<br/>[FR] DERIVES DE BENZIMIDAZOLES ET UTILISATION DE CEUX-CI EN TANT QUE LIGANDS DU RECEPTEUR VANILLOIDE
  申请人：AMGEN INC

  公开号：WO2004035549A1

  公开（公告）日：2004-04-29

  Compounds of formula (I) are useful in the treatment of vanilloid-receptor-meditated diseases, such as inflammatory or neuropathic pain and diseases involving sensory nerve function such as asthma, rheumatoid arthritis, osteoarthritis, inflammatory bowel disorders, urinary incontinence, migraine and psoriasis.

  式（I）的化合物在治疗辣椒素受体介导的疾病方面很有用，如炎症性或神经病痛以及涉及感觉神经功能的疾病，如哮喘、类风湿性关节炎、骨关节炎、炎症性肠道疾病、尿失禁、偏头痛和牛皮癣。
• <i>Cinchona</i> Alkaloid Catalyzed Sulfa-Michael Addition Reactions Leading to Enantiopure β-Functionalized Cysteines
  作者：Arjen C. Breman、Suze E. M. Telderman、Roy P. M. van Santen、Jamie I. Scott、Jan H. van Maarseveen、Steen Ingemann、Henk Hiemstra

  DOI：10.1021/acs.joc.5b01660

  日期：2015.11.6

  Sulfa-Michael additions to α,β-unsaturated N-acylated oxazolidin-2-ones and related α,β-unsaturated α-amino acid derivatives have been enantioselectively catalyzed by Cinchona alkaloids functionalized with a hydrogen bond donating group at the C6′ position. The series of Cinchona alkaloids includes known C6′ (thio)urea and sulfonamide derivatives and several novel species with a benzimidazole, squaramide

  α，β-不饱和N-酰化恶唑烷-2-酮和相关α，β-不饱和α-氨基酸衍生物的磺胺-迈克尔加成反应已通过在C6'位上带有氢键供体基团官能化的金鸡纳生物碱对映选择性催化。金鸡纳系列生物碱包括已知的C6'（硫）脲和磺酰胺衍生物，以及在C6'位置带有苯并咪唑，方胺或苯甲酰胺基团的几种新物种。磺酰胺特别适合用作双官能有机催化剂，因为它们使产物具有非常好的非对映选择性和高对映选择性。特别地，C6'磺酰胺催化与α，β-不饱和α-氨基酸衍生物的反应，以高达93：7的非对映体比例提供产物，主要异构体以高达99的ee形成％。随后将有机催化的磺胺-迈克尔加成产物加到α，β-不饱和α-氨基酸衍生物上，以高收率转化为对映体纯的β-官能化半胱氨酸，适用于天然化学连接。
• Novel Cinchona-Aminobenzimidazole Bifunctional Organocatalysts
  作者：Lei Zhang、Myoung-Mo Lee、Soo-Mi Lee、Jihye Lee、Maosheng Cheng、Byeong-Seon Jeong、Hyeung-geun Park、Sang-sup Jew

  DOI：10.1002/adsc.200900787

  日期：2009.12

  e with C(9S)-aminodihydroquinine or C(9R)-aminodihydroquinidine and successively applied to the Michael addition of dimethyl malonate to nitroolefins as very efficient chiral Lewis acid bifunctional organocatalysts (up to >99% ee).

  通过将5,7-双（三氟甲基）-2-氯苯并咪唑与C（9 S）-氨基二氢奎宁或C（9 R）-氨基二氢奎尼丁偶联，制备出高效的金鸡纳衍生的手性2-氨基苯并咪唑催化剂，并将其依次用于迈克尔加成反应丙二酸二甲酯转化为硝基烯烃，是非常有效的手性路易斯酸双官能有机催化剂（ee高达99％以上）。
• Vanilloid receptor ligands and their use in treatments
  申请人：Amgen Inc.

  公开号：US20040152690A1

  公开（公告）日：2004-08-05

  Therapeutic benzimidazoles 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, bums, 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.

  治疗苯并咪唑和含有苯并咪唑的组合物，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、炎症性肠病、炎症性眼疾、炎症性或不稳定的膀胱疾病、牛皮癣、带有炎症成分的皮肤疾病、慢性炎症病状、炎症性疼痛及相关的高敏感性和痛觉过敏、神经痛及相关的高敏感性和痛觉过敏、糖尿病神经病疼痛、烧伤后疼痛、交感神经维持性疼痛、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、伤口、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、由坏死性剂引起的胃病变、头发生长、血管运动或过敏性鼻炎、支气管疾病或膀胱疾病。
• VANILLOID RECEPTOR LIGANDS AND THEIR USE IN TREATMENTS
  申请人：Balan Chenera

  公开号：US20090143575A1

  公开（公告）日：2009-06-04

  Therapeutic benzimidazoles 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 necrotizing agents, hair growth, vasomotor or allergic rhinitis, bronchial disorders or bladder disorders.

  治疗苯并咪唑及其含量物，用于急性、炎症性和神经痛、牙痛、一般头痛、偏头痛、集群性头痛、混合血管和非血管综合症、紧张型头痛、一般炎症、关节炎、风湿性疾病、骨关节炎、炎症性肠病、炎症性眼病、炎症性或不稳定的膀胱疾病、牛皮癣、有炎症成分的皮肤病、慢性炎症状况、炎症性疼痛和相关的高敏感性和触痛、神经痛和相关的高敏感性和触痛、糖尿病神经病疼痛、烧伤后疼痛、交感神经维持的疼痛、去感觉综合症、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、伤口、烧伤、过敏性皮肤反应、瘙痒、白癜风、一般胃肠疾病、胃溃疡、十二指肠溃疡、腹泻、坏死性剂引起的胃损伤、头发生长、血管运动或过敏性鼻炎、支气管疾病或膀胱疾病。