1-phenethyl-1-azabicyclo<2.2.1>-3-heptene | 149494-50-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-phenethyl-1-azabicyclo<2.2.1>-3-heptene
• 英文别名: (-)-(1S,1'R)-2-(1'-Phenylethyl)-2-azabicyclo<2.2.1>hept-5-ene；(1S,4R)-2-((R)-1-phenylethyl)-2-azabicyclo[2,2,1]hept-5-ene；(1S,4R)-2-((R)-1-Phenylethyl)-2-azabicyclo[2.2.1]hept-5-ene；(1S,4R)-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene
• CAS: 149494-50-8
• 化学式: C₁₄H₁₇N
• 分子量: 199.296
• InChiKey: ZFTGYVZYKWHOPY-MBNYWOFBSA-N

物化性质

• 沸点：
  279.9±9.0 °C(predicted)
• 密度：
  1.076±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-phenethyl-1-azabicyclo<2.2.1>-3-heptene 在 palladium on activated charcoal 氢氧化钾 、 sodium hydroxide 、 硼烷四氢呋喃络合物 、 草酰氯 、 甲基锂 、 双氧水 、 双(三甲基硅烷基)氨基钾 、 1-羟基苯并三唑 、 二甲基亚砜 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 环己烯 为溶剂， 反应 19.41h， 生成 tert-butyl N-[2-[[(1S,4S,8R)-6-oxo-10-[(1R)-1-phenylethyl]-3,10-diazatricyclo[6.2.1.02,7]undec-2(7)-ene-4-carbonyl]amino]ethyl]carbamate
  参考文献：
  名称：

  Design and Asymmetric Synthesis of β-Strand Peptidomimetics

  摘要：

  We describe the asymmetric synthesis of non-peptidic compounds that feature rigid backbone conformations and present various side-chain functions. The key step in the synthesis of these compounds is the C-acylation of an appropriate ketone with a suitably protected aspartic acid derivative. The resulting dipeptide modules may be connected to form tetrapeptide mimics. Specifically is described the mimicry of a four-residue segment of CD4, the cellular receptor of HIV-1. The design was based on molecular modeling and the X-ray crystal structures of CD4 and intended to present the most important-side chains and backbone elements of the Phe43-Lys46 segment.

  DOI：

  10.1021/jo9522771
• 作为产物：
  描述：

  R(+)-alpha-甲基苄胺 、 alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 以 水 为溶剂， 生成 1-phenethyl-1-azabicyclo<2.2.1>-3-heptene
  参考文献：
  名称：

  Design and Asymmetric Synthesis of β-Strand Peptidomimetics

  摘要：

  We describe the asymmetric synthesis of non-peptidic compounds that feature rigid backbone conformations and present various side-chain functions. The key step in the synthesis of these compounds is the C-acylation of an appropriate ketone with a suitably protected aspartic acid derivative. The resulting dipeptide modules may be connected to form tetrapeptide mimics. Specifically is described the mimicry of a four-residue segment of CD4, the cellular receptor of HIV-1. The design was based on molecular modeling and the X-ray crystal structures of CD4 and intended to present the most important-side chains and backbone elements of the Phe43-Lys46 segment.

  DOI：

  10.1021/jo9522771

文献信息

• Absolute Configuration of 2-Substituted 2-Azabicyclo[2.2.1]hept-5-enes
  作者：Esteban Pombo-Villar、Jakob Boelsterli、Maria Magdalena Cid、Julien France、Beat Fuchs、Malcolm Walkinshaw、Hans-Peter Weber

  DOI：10.1002/hlca.19930760307

  日期：1993.5.12

  diastereoisomeric 2-substituted 2-azabicyclo[2.2.1]hept-5-enes 2–4 were prepared by aza-Diels-Alder reaction of cyclopentadiene with the corresponding methaniminium ions. Their relative configurations were deduced using 1H, 1H-ROESY experiments, and their absolute configurations were assigned from the crystal structure of the aziridinium derivative (−)-5. The absolute configuration of (+)-1, i.e. (1R)

  非对映体的2-取代-2-氮杂双环[2.2.1]庚-5-烯类2 - 4通过氮杂制备狄尔斯-阿尔德与相应methaniminium离子环戊二烯反应。使用1 H，1 H-ROESY实验推导了它们的相对构型，并从叠氮基衍生物（-）- 5的晶体结构中确定了它们的绝对构型。（+）- 1的绝对构型，即。（1 R），由CD光谱法确定。
• Substituted 2-azabicycles and their use as orexin receptor modulators
  申请人：Janssen Pharmaceutica NV

  公开号：US08969352B2

  公开（公告）日：2015-03-03

  The present invention is directed to compounds of Formula I: wherein X is N or CR1; Y is N or CR2; R1 is H, alkoxy, halo, triazolyl, pyrimidinyl, oxazolyl, isoxazole, oxadiazolyl, or pyrazolyl; R2 is H, alkyl, alkoxy, or halo; Z is NH or O; R3 is H, alkyl, alkoxy, halo, or triazolyl; R4 is H or alkyl; or R3 and R4, together with the atoms to which they are attached, form a 6-membered aryl ring or a 5- or 6-membered heteroaryl ring; R5 is pyridyl, pyrazinyl, or pyrimidinyl, wherein the pyridyl, pyrazinyl, or pyrimidinyl is optionally substituted with halo or alkyl; and n is 1 or 2. Methods of making the compounds of Formula I are also described. The invention also relates to pharmaceutical compositions comprising compounds of Formula I. Methods of using the compounds of the invention are also within the scope of the invention.

  本发明涉及式I的化合物：其中X为N或CR1; Y为N或CR2; R1为H、烷氧基、卤素、三唑基、嘧啶基、噁唑基、异噁唑基、噻二唑基或吡唑基; R2为H、烷基、烷氧基或卤素; Z为NH或O; R3为H、烷基、烷氧基、卤素或三唑基; R4为H或烷基; 或R3和R4与它们附着的原子一起形成6元芳基环或5-或6元杂芳基环; R5为吡啶基、吡嗪基或嘧啶基，其中吡啶基、吡嗪基或嘧啶基可以选择性地用卤素或烷基取代; n为1或2。还描述了制备式I化合物的方法。本发明还涉及包括式I化合物的制药组合物。使用本发明化合物的方法也在本发明的范围内。
• SUBSTITUTED 2-AZABICYCLES AND THEIR USE AS OREXIN RECEPTOR MODULATORS
  申请人：Janssen Pharmaceutica NV

  公开号：US20150174129A1

  公开（公告）日：2015-06-25

  The present invention is directed to compounds of Formula I: wherein X is N or CR 1 ; Y is N or CR 2 ; R 1 is H, alkoxy, halo, triazolyl, pyrimidinyl, oxazolyl, isoxazole, oxadiazolyl, or pyrazolyl; R 2 is H, alkyl, alkoxy, or halo; Z is NH or O; R 3 is H, alkyl, alkoxy, halo, or triazolyl; R 4 is H or alkyl; or R 3 and R 4 , together with the atoms to which they are attached, form a 6-membered aryl ring or a 5- or 6-membered heteroaryl ring; R 5 is pyridyl, pyrazinyl, or pyrimidinyl, wherein the pyridyl, pyrazinyl, or pyrimidinyl is optionally substituted with halo or alkyl; and n is 1 or 2. Methods of making the compounds of Formula I are also described. The invention also relates to pharmaceutical compositions comprising compounds of Formula I. Methods of using the compounds of the invention are also within the scope of the invention.

  本发明涉及式I的化合物：其中X为N或CR1；Y为N或CR2；R1为H，烷氧基，卤素，三唑基，嘧啶基，噁唑基，异噁唑基，噻二唑基或吡唑基；R2为H，烷基，烷氧基或卤素；Z为NH或O；R3为H，烷基，烷氧基，卤素或三唑基；R4为H或烷基；或R3和R4与它们所连接的原子一起形成一个6元芳基环或5或6元杂芳基环；R5为吡啶基，吡嗪基或嘧啶基，其中吡啶基，吡嗪基或嘧啶基可以选择性地用卤素或烷基取代；n为1或2。本发明还描述了制备式I化合物的方法。本发明还涉及包含式I化合物的制药组合物。使用本发明中的化合物的方法也在本发明的范围内。
• US2014/275118
  申请人：——

  公开号：——

  公开（公告）日：——
• US20140275118A1
  申请人：——

  公开号：——

  公开（公告）日：——