(S)-1-(2-bromophenyl)but-3-en-1-amine | 1225012-70-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-1-(2-bromophenyl)but-3-en-1-amine
• 英文别名: (1S)-1-(2-bromophenyl)but-3-en-1-amine
• CAS: 1225012-70-3
• 化学式: C₁₀H₁₂BrN
• 分子量: 226.116
• InChiKey: ZSFOAYKIAKFWNZ-JTQLQIEISA-N

物化性质

• 沸点：
  279.1±28.0 °C(Predicted)
• 密度：
  1.322±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-1-(2-bromophenyl)but-3-en-1-amine 在 三乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 24.0h， 生成 (S)-5,6-dihydro-6-(2-bromophenyl)pyridin-2(1H)-one
  参考文献：
  名称：

  RETRACTED: Asymmetric synthesis of highly enantioenriched 2-substituted piperidines and 6-substituted piperidine-2-ones by a combination enantioselective hydrazone allylation with ring closing metathesis

  摘要：

  An efficient method for the asymmetric synthesis of highly optically pure 2-substituted piperidines and 6-substituted piperidine-2-ones from aldehydes was developed by a sequence of enantioselective hydrazone allylation and ring closing metathesis. This method was found to be effective for a variety of substrates, showing substrate generality. The method's synthetic utility was illustrated in concise synthesis of the alkaloid (R)-(-)-coniine. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.061
• 作为产物：
  描述：

  (2-bromobenzylidene)benzohydrazide 在 甲醇 、 samarium diiodide 、 C₃₄H₃₂N₂O₂*F₆P^(1-)*H⁽¹⁺⁾ 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 17.0h， 生成 (S)-1-(2-bromophenyl)but-3-en-1-amine
  参考文献：
  名称：

  RETRACTED: Asymmetric synthesis of highly enantioenriched 2-substituted piperidines and 6-substituted piperidine-2-ones by a combination enantioselective hydrazone allylation with ring closing metathesis

  摘要：

  An efficient method for the asymmetric synthesis of highly optically pure 2-substituted piperidines and 6-substituted piperidine-2-ones from aldehydes was developed by a sequence of enantioselective hydrazone allylation and ring closing metathesis. This method was found to be effective for a variety of substrates, showing substrate generality. The method's synthetic utility was illustrated in concise synthesis of the alkaloid (R)-(-)-coniine. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.061

文献信息

• [EN] ( PYRROLIDIN-2 -YL) PHENYL DERIVATIVES FOR USE IN THE TREATMENT OF PAIN<br/>[FR] DÉRIVÉS (PYRROLIDIN-2-YL)PHÉNYLIQUES DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT DE LA DOULEUR
  申请人：ORGANON NV

  公开号：WO2010052198A1

  公开（公告）日：2010-05-14

  The invention relates to (pyrrolidin-2-yl)phenyl derivatives having the general Formula (I), wherein R1 is (C1-4)alkyl, halo(C1-4)alkyl, (C1-4)alkyloxy, or halo(C1-4)alkyloxy; R2 is H, (C1-4)alkyl, halo(C1-4)alkyl, (C1-4)alkyloxy, halo(C1-4)alkyloxy or halogen; R3 is H, (C1-4)alkyl or halo(C1-4)alkyl; R4 is H, (C1-4)alkyl or halo(C1-4)alkyl; R5 is H, (C1-4)alkyl or halo(C1-4)alkyl; or R4 and R5, when bonded to the same carbon atom, can together with the carbon atom form a spiro(C3-6)cycloalkyl group, optionally substituted with halogen; R6 is H, (C1-4)alkyl, halo(C1-4)alkyl, (C1-4)alkyloxy, halo(C1-4)alkyloxy or halogen; or a pharmaceutically acceptable salt thereof, to pharmaceutical compositions comprising the same, as well as to the use of these (pyrrolidin-2-yl)phenyl derivatives for the treatment of pain, such as neuropathic pain or inflammatory pain.

  该发明涉及具有通式（I）的（吡咯烷-2-基）苯基衍生物，其中R1为（C1-4）烷基，卤代（C1-4）烷基，（C1-4）烷氧基或卤代（C1-4）烷氧基；R2为H，（C1-4）烷基，卤代（C1-4）烷基，（C1-4）烷氧基，卤代（C1-4）烷氧基或卤素；R3为H，（C1-4）烷基或卤代（C1-4）烷基；R4为H，（C1-4）烷基或卤代（C1-4）烷基；R5为H，（C1-4）烷基或卤代（C1-4）烷基；或者R4和R5，当与同一碳原子结合时，可以与碳原子一起形成一个可选地被卤素取代的螺环（C3-6）环烷基基团；R6为H，（C1-4）烷基，卤代（C1-4）烷基，（C1-4）烷氧基，卤代（C1-4）烷氧基或卤素；或其药学上可接受的盐，以及包含它们的制药组合物，以及这些（吡咯烷-2-基）苯基衍生物用于治疗疼痛，如神经性疼痛或炎症性疼痛。
• (PYRROLIDIN-2-YL)PHENYL DERIVATIVES
  申请人：Grove Simon James Anthony

  公开号：US20100113493A1

  公开（公告）日：2010-05-06

  The invention relates to (pyrrolidin-2-yl)phenyl derivatives having the general Formula I wherein R 1 is (C 1-4 )alkyl, halo(C 1-4 )alkyl, (C 1-4 )alkyloxy, or halo(C 1-4 )alkyloxy; R 2 is H, (C 1-4 )alkyl, halo(C 1-4 )alkyl, (C 1-4 )alkyloxy, halo(C 1-4 )alkyloxy or halogen; R 3 is H, (C 1-4 )alkyl or halo(C 1-4 )alkyl; R 4 is H, (C 1-4 )alkyl or halo(C 1-4 )alkyl; R 5 is H, (C 1-4 )alkyl or halo-(C 1-4 )-alkyl; or R 4 and R 5 , when bonded to the same carbon atom, can together with the carbon atom form a spiro(C 3-6 )cycloalkyl group, optionally substituted with halogen; R 6 is H, (C 1-4 )alkyl, halo(C 1-4 )alkyl, (C 1-4 )alkyloxy, halo(C 1-4 )alkyloxy or halogen; or a pharmaceutically acceptable salt thereof, to pharmaceutical compositions comprising the same, as well as to the use of these (pyrrolidin-2-yl)phenyl derivatives for the treatment of pain, such as neuropathic pain or inflammatory pain.

  该发明涉及具有通式I的（吡咯啉-2-基）苯基衍生物，其中R1为（C1-4）烷基、卤代（C1-4）烷基、（C1-4）烷氧基或卤代（C1-4）烷氧基；R2为H、（C1-4）烷基、卤代（C1-4）烷基、（C1-4）烷氧基、卤代（C1-4）烷氧基或卤素；R3为H、（C1-4）烷基或卤代（C1-4）烷基；R4为H、（C1-4）烷基或卤代（C1-4）烷基；R5为H、（C1-4）烷基或卤代（C1-4）烷基；或者当R4和R5与同一碳原子结合时，它们可以与碳原子一起形成一个可选择地取代卤素的螺环（C3-6）环烷基基团；R6为H、（C1-4）烷基、卤代（C1-4）烷基、（C1-4）烷氧基、卤代（C1-4）烷氧基或卤素；或其药学上可接受的盐，以及含有这些（吡咯啉-2-基）苯基衍生物的药物组合物，以及这些（吡咯啉-2-基）苯基衍生物用于治疗疼痛，如神经痛或炎症性疼痛。
• (Pyrrolidin-2-yl)phenyl derivatives
  申请人：——

  公开号：US08188123B2

  公开（公告）日：2012-05-29

  The invention relates to (pyrrolidin-2-yl)phenyl derivatives having the general Formula I wherein R1 is (C1-4)alkyl, halo(C1-4)alkyl, (C1-4)alkyloxy, or halo(C1-4)alkyloxy; R2 is H, (C1-4)alkyl, halo(C1-4)alkyl, (C1-4)alkyloxy, halo(C1-4)alkyloxy or halogen; R3 is H, (C1-4)alkyl or halo(C1-4)alkyl; R4 is H, (C1-4)alkyl or halo(C1-4)alkyl; R5 is H, (C1-4)alkyl or halo-(C1-4)-alkyl; or R4 and R5, when bonded to the same carbon atom, can together with the carbon atom form a spiro(C3-6)cycloalkyl group, optionally substituted with halogen; R6 is H, (C1-4)alkyl, halo(C1-4)alkyl, (C1-4)alkyloxy, halo(C1-4)alkyloxy or halogen; or a pharmaceutically acceptable salt thereof, to pharmaceutical compositions comprising the same, as well as to the use of these (pyrrolidin-2-yl)phenyl derivatives for the treatment of pain, such as neuropathic pain or inflammatory pain.

  本发明涉及具有一般式I的（吡咯烷-2-基）苯基衍生物，其中R1为（C1-4）烷基，卤代（C1-4）烷基，（C1-4）烷氧基或卤代（C1-4）烷氧基；R2为H，（C1-4）烷基，卤代（C1-4）烷基，（C1-4）烷氧基，卤代（C1-4）烷氧基或卤素；R3为H，（C1-4）烷基或卤代（C1-4）烷基；R4为H，（C1-4）烷基或卤代（C1-4）烷基；R5为H，（C1-4）烷基或卤代（C1-4）烷基；或当与同一碳原子结合时，R4和R5可以与碳原子一起形成一个spiro（C3-6）环烷基，可选择性地被卤素取代；R6为H，（C1-4）烷基，卤代（C1-4）烷基，（C1-4）烷氧基，卤代（C1-4）烷氧基或卤素；或其药学上可接受的盐，以及包含它们的制药组合物，以及这些（吡咯烷-2-基）苯基衍生物用于治疗疼痛，如神经病理性疼痛或炎症性疼痛。
• New Generation of Highly Reactive Allylborating Agents For Cu(I)-Catalyzed Allylation of Chiral Sulfinylimines
  作者：Michael S. Alexeev、Tatyana V. Strelkova、Michail M. Ilyin, Jr.、Yulia V. Nelyubina、Ivan A. Bespalov、Michael Medvedev、Victor N Khrustalev、Nikolai Kuznetsov

  DOI：10.1039/d4ob00291a

  日期：——

  active reagents is an attractive strategy that meets the modern principles of sustainable development of chemistry. In the current study, we for the first time describe the method and general principles of Cu(I)-catalyzed allylation of imines with amine adducts of allylic triorganoboranes. Triallylborane is an extremely reactive compound and cannot be used for the catalytic allylation of imines, whereas

  使用高活性试剂实施选择性催化过程是一种有吸引力的策略，符合化学可持续发展的现代原则。在本研究中，我们首次描述了Cu( I )催化亚胺与烯丙基三有机硼烷胺加合物的烯丙基化反应的方法和一般原理。三烯丙基硼烷是一种极其活泼的化合物，不能用于亚胺的催化烯丙基化，而其胺加合物是理想的催化底物。胺片段的结构成功地平衡了烯丙基硼试剂的安全性、选择性和稳定性，使其在催化烯丙基化反应中表现出高活性，超过任何已知的烯丙基硼烷许多倍。获得的结果得到定量动力学数据和 DFT 计算的支持。该系统的催化功效在亚磺酰亚胺模型（23 个例子）上得到了证明。实现了高达 >99% 的高非对映选择性，包​​括克级合成 2-羟基苯基衍生物。考虑到三烯基硼烷（AAT）的胺加合物的高反应活性和无与伦比的原子经济性，它们可以被认为是Cu（ I ）和其他合适金属催化剂的潜在烯丙基化试剂。
• ( PYRROLIDIN-2 -YL) PHENYL DERIVATIVES FOR USE IN THE TREATMENT OF PAIN
  申请人：N.V. Organon

  公开号：EP2356105A1

  公开（公告）日：2011-08-17