3,3-dimethyl-N-(2,2,2-trifluoroethyl)butanamide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3,3-dimethyl-N-(2,2,2-trifluoroethyl)butanamide
• 化学式: C₈H₁₄F₃NO
• 分子量: 197.2
• InChiKey: WMYMXHHKZGPKBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3-dimethyl-N-(2,2,2-trifluoroethyl)butanamide 在 silver tetrafluoroborate 、 acetyl hypobromite 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 生成 Γ-二甲基丁内酯
  参考文献：
  名称：

  Synthesis of Lactones via C–H Functionalization of Nonactivated C(sp³)–H Bonds

  摘要：

  An electron-deficient amide is utilized as a directing group to functionalize nonactivated C(sp(3))-H bonds through radical 1,5-hydrogen abstraction. The gamma-bromoamides formed are subsequently converted to gamma-lactones under mild conditions. The method described is not limited to tertiary and secondary positions but also allows functionalization of primary nonactivated sp(3)-hybridized positions in a one-pot sequence. In addition, the broad functional group tolerance renders this method suitable for the late-stage introduction of gamma-lactones into complex carbon frameworks.

  DOI：

  10.1021/acs.orglett.6b03371
• 作为产物：
  描述：

  3,3-二甲基-1-丁酸 、 2,2,2-三氟乙胺盐酸盐 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以69%的产率得到3,3-dimethyl-N-(2,2,2-trifluoroethyl)butanamide
  参考文献：
  名称：

  Synthesis of Lactones via C–H Functionalization of Nonactivated C(sp³)–H Bonds

  摘要：

  An electron-deficient amide is utilized as a directing group to functionalize nonactivated C(sp(3))-H bonds through radical 1,5-hydrogen abstraction. The gamma-bromoamides formed are subsequently converted to gamma-lactones under mild conditions. The method described is not limited to tertiary and secondary positions but also allows functionalization of primary nonactivated sp(3)-hybridized positions in a one-pot sequence. In addition, the broad functional group tolerance renders this method suitable for the late-stage introduction of gamma-lactones into complex carbon frameworks.

  DOI：

  10.1021/acs.orglett.6b03371

文献信息

• PROCESS FOR THE PREPARATION OF DIHYDROPYRROLE DERIVATIVES
  申请人：Syngenta Participations AG

  公开号：US20160073631A1

  公开（公告）日：2016-03-17

  The present invention provides stereoselective processes for the preparation of compounds of formula (I) wherein P is phenyl, naphthyl, a 6-membered heteroaryl group containing one or two nitrogen atoms as ring members, or a 10-membered bicyclic heteroaryl group containing one or two nitrogen atoms as ring members, and wherein the phenyl, naphthyl and heteroaryl groups are optionally substituted; R 1 is chlorodifluoromethyl or trifluoromethyl; R 2 is optionally substituted aryl or optionally substituted heteroaryl; n is 0 or 1; including the process comprising (a-i) reacting a compound of formula II wherein P, R 1 and R 2 are as defined for the compound of formula I; with nitromethane in the presence a chiral catalyst to give a compound of formula III wherein P, R 1 and R 2 are as defined for the compound of formula I; and (a-ii) reductively cyclising the compound of formula III to give the compound of formula I. The invention also provides intermediates useful for processes for the synthesis of compounds of formula (I).

  本发明提供了用于制备式(I)化合物的立体选择性过程，其中 P为苯基、萘基、含有一个或两个氮原子作为环成员的6元杂芳基，或含有一个或两个氮原子作为环成员的10元双环杂芳基，其中苯基、萘基和杂芳基可以选择性地被取代； R1为氯二氟甲基或三氟甲基； R2为可以选择性取代的芳基或可以选择性取代的杂芳基； n为0或1； 包括以下过程 (a-i)将式II化合物与硝基甲烷在手性催化剂存在下反应，得到式III化合物； 其中P、R1和R2如式I化合物中所定义； (a-ii)将式III化合物还原环化，得到式I化合物。 本发明还提供了用于合成式(I)化合物的过程的中间体。
• [EN] CANNABINOID RECEPTOR MODULATORS<br/>[FR] MODULATEURS DES RÉCEPTEURS DE CANNABINOÏDES
  申请人：ARENA PHARM INC

  公开号：WO2011025541A1

  公开（公告）日：2011-03-03

  The present invention relates to certain compounds of Formula Ia and pharmaceutical compositions thereof that modulate the activity of the cannabinoid CB2 receptor. The present invention further relates to certain compounds of Formula Ia and pharmaceutical compositions thereof that modulate the activities of both the CB1 receptor and the CB2 receptor. Compounds of the present invention and pharmaceutical compositions thereof are directed to methods useful in the treatment of: pain, for example bone and joint pain, muscle pain, dental pain, migraine and other headache pain, inflammatory pain, neuropathic pain, pain that occurs as an adverse effect of therapeutics and pain associated with osteoarthritis; hyperalgesia; allodynia; inflammatory hyperalgesia; neuropathic hyperalgesia; acute nociception; osteoporosis; multiple sclerosis-associated spasticity; autoimmune disorders; allergic reactions; CNS inflammation; atherosclerosis; undesired immune cell activity and inflammation; age-related macular degeneration; cough; leukemia; lymphoma; CNS tumors; prostate cancer; Alzheimer's disease; stroke-induced damage; dementia; amyotrophic lateral sclerosis, and Parkinson's disease.

  本发明涉及某些化合物Ia的配方和调节大麻素CB2受体活性的药物组合物。本发明还涉及某些化合物Ia的配方和药物组合物，其调节CB1受体和CB2受体的活性。本发明的化合物和药物组合物用于治疗以下疾病的方法：疼痛，例如骨骼和关节疼痛，肌肉疼痛，牙痛，偏头痛和其他头痛，炎症性疼痛，神经痛，作为治疗的不良反应而发生的疼痛以及与骨关节炎相关的疼痛；痛觉过敏；触觉过敏；炎症性痛觉过敏；神经痛觉过敏；急性疼痛感；骨质疏松症；多发性硬化症相关的痉挛；自身免疫性疾病；过敏反应；中枢神经系统炎症；动脉粥样硬化；不良的免疫细胞活性和炎症；年龄相关的黄斑变性；咳嗽；白血病；淋巴瘤；中枢神经系统肿瘤；前列腺癌；阿尔茨海默病；中风引起的损伤；痴呆症；肌萎缩侧索硬化和帕金森病。
• CANNABINOID RECEPTOR MODULATORS
  申请人：Jones Robert M.

  公开号：US20120214766A1

  公开（公告）日：2012-08-23

  The present invention relates to certain compounds of Formula Ia and pharmaceutical compositions thereof that modulate the activity of the cannabinoid CB2 receptor. The present invention further relates to certain compounds of Formula Ia and pharmaceutical compositions thereof that modulate the activities of both the CB1 receptor and the CB2 receptor. Compounds of the present invention and pharmaceutical compositions thereof are directed to methods useful in the treatment of: pain, for example bone and joint pain, muscle pain, dental pain, migraine and other headache pain, inflammatory pain, neuropathic pain, pain that occurs as an adverse effect of therapeutics and pain associated with osteoarthritis; hyperalgesia; allodynia; inflammatory hyperalgesia; neuropathic hyperalgesia; acute nociception; osteoporosis; multiple sclerosis-associated spasticity; autoimmune disorders; allergic reactions; CNS inflammation; atherosclerosis; undesired immune cell activity and inflammation; age-related macular degeneration; cough; leukemia; lymphoma; CNS tumors; prostate cancer; Alzheimer's disease; stroke-induced damage; dementia; amyotrophic lateral sclerosis, and Parkinson's disease.

  本发明涉及公式Ia的某些化合物及其制药组合物，其调节大麻素CB2受体的活性。本发明还涉及公式Ia的某些化合物及其制药组合物，其调节CB1受体和CB2受体的活性。本发明的化合物和制药组合物适用于治疗以下疾病的方法：疼痛，例如骨骼和关节疼痛，肌肉疼痛，牙痛，偏头痛和其他头痛，炎性疼痛，神经痛，由治疗副作用引起的疼痛和与骨关节炎相关的疼痛；过敏症；炎性过敏症；神经病性过敏症；急性疼痛感受；骨质疏松症；多发性硬化症相关痉挛；自身免疫疾病；过敏反应；中枢神经系统炎症；动脉粥样硬化；不良的免疫细胞活动和炎症；年龄相关的黄斑变性；咳嗽；白血病；淋巴瘤；中枢神经系统肿瘤；前列腺癌；阿尔茨海默病；中风引起的损伤；痴呆症；肌萎缩性侧索硬化症和帕金森病。
• NOVEL HETEROCYCLIC COMPOUNDS
  申请人：Jain Rajesh

  公开号：US20100311732A1

  公开（公告）日：2010-12-09

  The present invention relates to novel compounds of Formula I, their pharmaceutically acceptable derivatives, tautomeric forms, stereoisomers including R and S isomers, polymorphs, prodrugs, metabolites, salts or solvates thereof. The invention also relates to the processes for the synthesis of novel compounds of Formula I, their pharmaceutically acceptable derivatives, tautomeric forms, stereoisomers, polymorphs, prodrugs, metabolites, salts or solvates thereof. The present invention also provides pharmaceutical compositions comprising compounds of Formula I and methods of treating or preventing one or more conditions that may be regulated or normalized via inhibition of dipeptidyl peptidase IV (DPP-IV).

  本发明涉及一种新型I式化合物，其药学上可接受的衍生物、互变异构体、立体异构体（包括R和S异构体）、多晶形、前药、代谢物、盐或溶剂化物。本发明还涉及制备新型I式化合物、其药学上可接受的衍生物、互变异构体、立体异构体、多晶形、前药、代谢物、盐或溶剂化物的方法。本发明还提供了包含I式化合物的制药组合物和通过抑制二肽基肽酶IV（DPP-IV）来治疗或预防可能通过调节或规范的一种或多种情况的方法。
• Cannabinoid receptor modulators
  申请人：Arena Pharmaceuticals, Inc.

  公开号：US10632134B2

  公开（公告）日：2020-04-28

  Provided are certain methods useful in the treatment of cancer comprising administering a compound of Formula Ia and pharmaceutical compositions thereof that modulate the activity of the cannabinoid CB2 receptor;

  本文提供了某些用于治疗癌症的方法，包括施用调节大麻素 CB2 受体活性的式 Ia 化合物及其药物组合物；