2-溴-4-叔丁基苯甲醛 | 246139-77-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-溴-4-叔丁基苯甲醛
• 中文别名: 6-叔丁基吡啶-3-甲醛
• 英文名称: 2-bromo-4-tert-butylbenzaldehyde
• CAS: 246139-77-5
• 化学式: C₁₁H₁₃BrO
• mdl: MFCD09029651
• 分子量: 241.128
• InChiKey: WVCSDKHZXVXDMV-UHFFFAOYSA-N

物化性质

• 沸点：
  274.9±28.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2913000090

反应信息

• 作为反应物：
  描述：

  2-溴-4-叔丁基苯甲醛 在 吡啶 、 palladium diacetate 、 sodium hydroxide 、 草酰氯 、 1,3-双(二苯基膦)丙烷 、 sodium hydride 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 15.0h， 生成 ethyl 2-[(1E)-2-(N-(2H,3H-benzo[e]1,4-dioxan-6-yl)carbamoyl)vinyl]-5-(tert-butyl)benzoate
  参考文献：
  名称：

  Discovery of Potent, Orally Available Vanilloid Receptor-1 Antagonists. Structure−Activity Relationship of N-Aryl Cinnamides

  摘要：

  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).

  DOI：

  10.1021/jm049485i
• 作为产物：
  描述：

  4-叔丁基甲苯 在 sodium bromate 、 sodium hydrogensulfite 作用下， 以 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 8.0h， 生成 2-溴-4-叔丁基苯甲醛
  参考文献：
  名称：

  用于不对称光氧化还原氰基烷基化的双环金属化吲唑铑手性催化剂。

  摘要：

  介绍了一种新型的双环金属铑（III）催化剂，该催化剂包含两个惰性的环金属化的6-叔丁基-2-苯基-2H-吲唑配体和两个不稳定的乙腈。通过使用单氟化水杨基恶唑啉的手性辅助介导的方法获得单一对映体（> 99％ee）。这种新型的手性金属络合物能够催化可见光诱导的2-酰基咪唑的对映选择性α-氰基烷基化反应，该化合物在不对称自由基化学反应中同时起手性路易斯酸催化剂的双重作用。作为可见光诱导的氧化还原化学的光氧化还原催化剂（12个实例，产率高达80％，dr为4：1，ee为95％）。

  DOI：

  10.1002/chem.201903369

文献信息

• Vanilloid receptor ligands and their use in treatments
  申请人：——

  公开号：US20030195201A1

  公开（公告）日：2003-10-16

  Compounds having the general structure 1 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, pruritis, 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.

  具有一般结构1的化合物以及含有它们的组合物，用于治疗急性疼痛、炎症性和神经性疼痛、牙痛、普通头痛、偏头痛、丛集性头痛、混合性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、炎症性或不稳定的膀胱病、银屑病、具有炎症成分的皮肤疾病、慢性炎症状况、炎症性疼痛及其相关的过度疼痛和异常疼痛、神经性疼痛及其相关的过度疼痛和异常疼痛、糖尿病性神经病疼痛、灼痛、交感神经维持的疼痛、去神经综合症、哮喘、上皮组织损伤或功能障碍、单纯疱疹、在呼吸、生殖泌尿、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、一般胃肠病、胃溃疡、十二指肠溃疡、腹泻、由坏死性剂引起的胃部病变、毛发生长、血管运动性或过敏性鼻炎、支气管障碍或膀胱障碍。
• Asymmetric Hydrogenation of Ketones with H₂and Ruthenium Catalysts Containing Chiral Tetradentate S₂N₂Ligands
  作者：Ruth Patchett、Iris Magpantay、Lionel Saudan、Christoph Schotes、Antonio Mezzetti、Francesco Santoro

  DOI：10.1002/anie.201304844

  日期：2013.9.23

  Getting more for less: In the presence of H2 and a base, air‐ and moisture‐tolerant RuII complexes catalyze the hydrogenation of ketones and aldehydes with excellent activity and chemoselectivity, and with enantioselectivity of up to 95 % under mild conditions. The ratio of substrate to catalyst can be lowered to 106:1. The reactions tolerate scale‐up and can be carried out with almost no solvent. A base‐free

  事半功倍：在H 2和碱的存在下，耐空气和潮气的Ru II络合物以优异的活性和化学选择性，在温和条件下的对映选择性高达95％，催化酮和醛的氢化反应。底物与催化剂的比例可以降低至10 6：1。该反应可按比例放大，几乎可以在没有溶剂的情况下进行。无碱方法可用于对碱敏感的底物。
• Substituted sulfonylaminoarylmethyl cyclopropanecarboxamide as VR1 receptor antagonists
  申请人：Hanazawa Takeshi

  公开号：US20060211741A1

  公开（公告）日：2006-09-21

  This invention provides a compound of the formula (I): wherein A and B are independently CR 12 or N; D and E are each independently CR 9 or N; R 1 represents (C 1 -C 6 )alkyl; R 2 represents hydrogen, halogen, hydroxy, (C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkyl, hydroxy(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy or (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl; R 3 , R 4 , R 5 , R 6 , R 10 and R 11 each independently represent hydrogen, halogen, (C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, hydroxy(C 1 -C 6 )alkyl or (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl; or R 3 and R 4 are taken together with the carbon atom to which they are attached to form a 3- to 7-membered carbocyclic ring or heterocyclic ring in which one or two non-adjacent carbon atoms are optionally replaced by an oxygen atom, a sulfur atom or NH; R 7 and R 9 each independently represent hydrogen, halogen, (C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkyl, hydroxy(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, hydroxy(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylthio, (C 1 -C 6 )alkylsulfinyl, (C 1 -C 6 )alkylsulfonyl, NH 2 , [(C 1 -C 6 )alkyl]NH—, [(C 1 -C 6 )alkyl] 2 N—, H 2 N—(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkyl-NH—(C 1 -C 6 )alkoxy, [(C 1 -C 6 )alkyl] 2 N(C 1 -C 6 )alkoxy; H 2 N—(C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, (C 1 C 6 )alkyl-NH—(C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, [(C 1 -C 6 )alkyl] 2 N(C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl or 5- or 6-membered heterocyclic ring containing at least one nitrogen atom; R 8 represents halogen, (C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkyl, hydroxy(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, hydroxy(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkylsulfonyl, halo(C 1 -C 6 )alkylsulfinyl, halo(C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkylthio, [(C 1 -C 6 )alkyl]NH— or [(C 1 -C 6 )alkyl] 2 N—; or R 7 and R 8 , when E is CR 9 , are taken together with the carbon atoms to which they are attached form a 5-8 membered carbocyclic or heterocyclic ring, in which one or two non-adjacent carbon atoms are optionally replaced by oxygen, sulfur, N or NH groups, wherein the carbocyclic ring or the heterocyclic ring is unsubstituted or substituted with one or more substituents each independently selected from the group consisting of hydroxy, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy and hydroxy(C 1 -C 6 )alkyl; and R 12 represents hydrogen, halogen, (C 1 -C 6 )alkyl or hydroxy(C 1 -C 6 )alkyl; or a pharmaceutically acceptable salt or solvate thereof. These compounds are useful for the treatment of disease conditions caused by overactivation of VR1 receptor such of pain, or the like in mammalian. This invention also provides a pharmaceutical composition comprising the above compound.

  这项发明提供了一个化合物的结构式(I)：其中A和B分别独立地为CR12或N；D和E分别独立地为CR9或N；R1代表(C1-C6)烷基；R2代表氢、卤素、羟基、(C1-C6)烷基、卤代(C1-C6)烷基、羟基(C1-C6)烷基、(C1-C6)氧烷基或(C1-C6)氧烷基-(C1-C6)烷基；R3、R4、R5、R6、R10和R11分别独立地代表氢、卤素、(C1-C6)烷基、卤代(C1-C6)烷基、(C1-C6)氧烷基、羟基(C1-C6)烷基或(C1-C6)氧烷基-(C1-C6)烷基；或者R3和R4一起与它们连接的碳原子形成一个3-至7-成员的碳环或杂环，其中一个或两个非相邻的碳原子可以选择性地被氧原子、硫原子或NH取代；R7和R9分别独立地代表氢、卤素、(C1-C6)烷基、卤代(C1-C6)烷基、羟基(C1-C6)烷基、(C1-C6)氧烷基、羟基(C1-C6)氧烷基、(C1-C6)氧烷基-(C1-C6)烷基、(C1-C6)氧烷基-(C1-C6)氧烷基、(C1-C6)烷基硫、(C1-C6)烷基亚硫基、(C1-C6)烷基磺基、NH2、[(C1-C6)烷基]NH—、[(C1-C6)烷基]2N—、H2N—(C1-C6)氧烷基、(C1-C6)烷基-NH—(C1-C6)氧烷基、[(C1-C6)烷基]2N(C1-C6)氧烷基；H2N—(C1-C6)氧烷基-(C1-C6)烷基、(C1C6)烷基-NH—(C1-C6)氧烷基-(C1-C6)烷基、[(C1-C6)烷基]2N(C1-C6)氧烷基-(C1-C6)烷基或含有至少一个氮原子的5-或6-成员杂环，R8代表卤素、(C1-C6)烷基、卤代(C1-C6)烷基、羟基(C1-C6)烷基、(C1-C6)氧烷基、羟基(C1-C6)氧烷基、(C1-C6)氧烷基-(C1-C6)烷基、(C1-C6)氧烷基-(C1-C6)氧烷基、卤代(C1-C6)烷基磺基、卤代(C1-C6)烷基亚硫基、卤代(C1-C6)烷基氧基、卤代(C1-C6)烷基硫基、[(C1-C6)烷基]NH—或[(C1-C6)烷基]2N—；或者当E为CR9时，R7和R8一起与它们连接的碳原子形成一个5-8成员的碳环或杂环，其中一个或两个非相邻的碳原子可以选择性地被氧、硫、N或NH基团取代，其中碳环或杂环未取代或取代有一个或多个取代基，每个取代基独立地选自羟基、(C1-C6)烷基、(C1-C6)氧烷基和羟基(C1-C6)烷基；R12代表氢、卤素、(C1-C6)烷基或羟基(C1-C6)烷基；或其药学上可接受的盐或溶剂。这些化合物对于治疗由VR1受体过度激活引起的疾病状况，如哺乳动物中的疼痛等，是有用的。这项发明还提供了包含上述化合物的药物组合物。
• Copper-Catalyzed Recycling of Halogen Activating Groups via 1,3-Halogen Migration
  作者：R. David Grigg、Ryan Van Hoveln、Jennifer M. Schomaker

  DOI：10.1021/ja306446m

  日期：2012.10.3

  A Cu(I)-catalyzed 1,3-halogen migration reaction effectively recycles an activating group by transferring bromine or iodine from a sp(2) to a benzylic carbon with concomitant borylation of the Ar-X bond. The resulting benzyl halide can be reacted in the same vessel under a variety of conditions to form an additional carbon-heteroatom bond. Cross-over experiments using an isotopically enriched bromide

  Cu(I) 催化的 1,3-卤素迁移反应通过将溴或碘从 sp(2) 转移到苄基碳并伴随 Ar-X 键的硼化，有效地回收了活化基团。所得苄基卤可以在同一容器中在各种条件下反应以形成额外的碳-杂原子键。使用同位素富集的溴化物源的交叉实验支持 Br 的分子内转移。假设该反应通过邻卤苯乙烯的马尔科夫尼科夫氢铜反应、所得 Cu(I) 络合物氧化加成到 Ar-X 键中、还原消除新的 sp(3) CX 键和最终硼化反应进行Ar-Cu(I) 物种翻转催化循环。
• METAL COMPLEXES
  申请人：MERCK PATENT GMBH

  公开号：US20190315787A1

  公开（公告）日：2019-10-17

  The present invention relates to metal complexes and to electronic devices, in particular organic electroluminescent devices, containing these metal complexes.

  本发明涉及金属配合物和电子器件，特别是包含这些金属配合物的有机电致发光器件。