1-chloro-5,5-difluorohexane | 651724-08-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 1-chloro-5,5-difluorohexane
• 英文别名: 5,5-difluoro-1-chlorohexane
• CAS: 651724-08-2
• 化学式: C₆H₁₁ClF₂
• mdl: MFCD19236204
• 分子量: 156.603
• InChiKey: MMUIXRJHOQQROH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-chloro-5,5-difluorohexane 在 三丁基膦 、 sodium hydride 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 (2-{2-[4-(5,5-Difluoro-hexyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl]-ethoxy}-phenyl)-acetic acid methyl ester
  参考文献：
  名称：

  Benzoxazinones as PPARγ Agonists. 2. SAR of the Amide Substituent and In Vivo Results in a Type 2 Diabetes Model

  摘要：

  A series of benzoxazinones has been synthesized and tested for PPARgamma agonist activity. Synthetic approaches were developed to provide either racemic or chiral compounds. In vitro functional potency could be measured through induction of the aP2 gene, a target of PPARgamma. These studies revealed that compounds with large aliphatic chains at the nitrogen of the benzoxazinone were the most potent. Substitution of the chain was tolerated and in many cases enhanced the in vitro potency of the compound. Select compounds were further tested for metabolic stability, oral bioavailability in rats, and efficacy in db/db mice after 11 days of dosing. In vivo analysis with 13 and 57 demonstrated that the series has potential for the treatment of type 2 diabetes.

  DOI：

  10.1021/jm0301888
• 作为产物：
  描述：

  6-氯-2-己酮 在 二乙胺基三氟化硫 作用下， 生成 1-chloro-5,5-difluorohexane
  参考文献：
  名称：

  Benzoxazinones as PPARγ Agonists. 2. SAR of the Amide Substituent and In Vivo Results in a Type 2 Diabetes Model

  摘要：

  A series of benzoxazinones has been synthesized and tested for PPARgamma agonist activity. Synthetic approaches were developed to provide either racemic or chiral compounds. In vitro functional potency could be measured through induction of the aP2 gene, a target of PPARgamma. These studies revealed that compounds with large aliphatic chains at the nitrogen of the benzoxazinone were the most potent. Substitution of the chain was tolerated and in many cases enhanced the in vitro potency of the compound. Select compounds were further tested for metabolic stability, oral bioavailability in rats, and efficacy in db/db mice after 11 days of dosing. In vivo analysis with 13 and 57 demonstrated that the series has potential for the treatment of type 2 diabetes.

  DOI：

  10.1021/jm0301888

文献信息

• Substituted xanthine derivatives
  申请人：Tung Roger D.

  公开号：US20090239886A1

  公开（公告）日：2009-09-24

  This invention relates to novel compounds that are substituted xanthine derivatives and pharmaceutically acceptable salts thereof. For example, this invention relates to novel substituted xanthine derivatives that are derivatives of pentoxifylline. This invention also provides compositions comprising one or more compounds of this invention and a carrier and the use of the disclosed compounds and compositions in methods of treating diseases and conditions for which pentoxifylline and related compounds are beneficial.

  本发明涉及新型化合物，即取代黄嘌呤衍生物及其药学上可接受的盐。例如，本发明涉及新型取代黄嘌呤衍生物，它们是戊酰异丙基黄嘌呤的衍生物。本发明还提供了包含本发明中的一种或多种化合物和载体的组合物，以及把所述化合物和组合物用于治疗戊酰异丙基黄嘌呤和相关化合物有益的疾病和病况的方法。
• [EN] SUBSTITUTED XANTHINE DERIVATIVES<br/>[FR] DÉRIVÉS DE XANTHINE SUBSTITUÉS
  申请人：CONCERT PHARMACEUTICALS INC

  公开号：WO2011028835A1

  公开（公告）日：2011-03-10

  This invention relates to novel compounds that are substituted xanthine derivatives and pharmaceutically acceptable salts thereof. For example, this invention relates to novel substituted xanthine derivatives that are derivatives of pentoxifylline. This invention also provides compositions comprising one or more compounds of this invention and a carrier and the use of the disclosed compounds and compositions in methods of treating diseases and conditions for which pentoxifylline and related compounds are beneficial.

  本发明涉及新型化合物，它们是取代黄嘌呤衍生物及其药学上可接受的盐。例如，本发明涉及新型取代黄嘌呤衍生物，它们是戊申酰丙胺的衍生物。本发明还提供了包含本发明化合物之一或多个和载体的组合物以及使用所披露的化合物和组合物治疗戊申酰丙胺和相关化合物有益的疾病和病状的方法。
• SUBSTITUTED XANTHINE DERIVATIVES
  申请人：Tung Roger D.

  公开号：US20110053961A1

  公开（公告）日：2011-03-03

  This invention relates to novel compounds that are substituted xanthine derivatives and pharmaceutically acceptable salts thereof. For example, this invention relates to novel substituted xanthine derivatives that are derivatives of pentoxifylline. This invention also provides compositions comprising one or more compounds of this invention and a carrier and the use of the disclosed compounds and compositions in methods of treating diseases and conditions for which pentoxifylline and related compounds are beneficial.

  本发明涉及一种新型化合物，它们是取代黄嘌呤衍生物及其药学上可接受的盐。例如，本发明涉及一种新型的取代黄嘌呤衍生物，它们是戊酰苄氨基甲基黄嘌呤的衍生物。本发明还提供了包括本发明中的一个或多个化合物和载体的组合物，并且揭示了这些化合物和组合物在治疗戊酰苄氨基甲基黄嘌呤和相关化合物有益的疾病和病症的方法中的应用。
• Catalytic HF Shuttling between Fluoroalkanes and Alkynes**
  作者：Shannon E. S. Farley、Daniel Mulryan、Feriel Rekhroukh、Andreas Phanopoulos、Mark R. Crimmin

  DOI：10.1002/anie.202317550

  日期：2024.1.25

  In this paper, we report BF₃ ⋅ OEt₂ as a catalyst to shuttle equivalents of HF from a fluoroalkane to an alkyne. Reactions of terminal and internal aliphatic alkynes led to formation of difluoroalkane products, while diarylalkynes can be selectively converted into fluoroalkenes. The method tolerates numerous sensitive functional groups including halogen, protected amine, ester and thiophene substituents. Mechanistic studies (DFT, probe experiments) suggest the catalyst is involved in both the defluorination and fluorination steps, with BF₃ acting as a Lewis acid and OEt₂ a weak Lewis base that mediates proton transfer. In certain cases, the interconversion of fluoroalkene and difluoroalkane products was found to be reversible. The new catalytic system was applied to demonstrate proof‐of‐concept recycling of poly(vinylidene difluoride).

  摘要 在本文中，我们报告了 BF3 ⋅ OEt2 作为催化剂将等当量的 HF 从氟烷烃穿梭到炔烃的情况。末端和内部脂肪族炔烃的反应可形成二氟烷烃产物，而二芳基炔烃则可选择性地转化为氟烯烃。该方法可容忍多种敏感官能团，包括卤素、受保护的胺、酯和噻吩取代基。机理研究（DFT、探针实验）表明，催化剂参与了脱氟和氟化两个步骤，其中 BF3 起着路易斯酸的作用，而 OEt2 则是介导质子转移的弱路易斯碱。在某些情况下，氟烯烃和二氟烷烃产物的相互转化是可逆的。新催化系统被用于演示聚偏二氟乙烯的概念验证回收。
• SUBSTITUED XANTHINE DERIVATIVES
  申请人：Concert Pharmaceuticals Inc.

  公开号：EP3199203A1

  公开（公告）日：2017-08-02

  A pharmaceutical composition comprising: a. an effective amount of a compound of Formula B: or a pharmaceutically acceptable salt thereof; b. a second therapeutic agent selected from insulin or insulin analogues, glucagon-like-peptide-1 (GLP-1) receptor agonists, sulfonylurea agents, biguanide agents, alpha-glucosidase inhibitors, PPAR agonists, meglitinide agents, dipeptidyl-peptidase (DPP) IV inhibitors, phosphodiesterase inhibitors, amylin agonists, CoEnzyme A inhibitors, and antiobesity agents; and c. a pharmaceutically acceptable car.

  一种药物组合物，包括 a. 有效量的式 B 化合物： 或其药学上可接受的盐； b. 第二种治疗剂，选自胰岛素或胰岛素类似物、胰高血糖素样肽-1 (GLP-1) 受体激动剂、磺酰脲类药物、双胍类药物、α-葡萄糖苷酶抑制剂、PPAR 激动剂、甲格列脲类药物、二肽基肽酶 (DPP) IV 抑制剂、磷酸二酯酶抑制剂、淀粉样蛋白激动剂、辅酶 A 抑制剂和抗肥胖药；以及 c. 医药上可接受的载体。