8-methyl-2-propanoyl-8-azabicyclo<3.2.1>oct-2-ene | 156038-49-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-methyl-2-propanoyl-8-azabicyclo<3.2.1>oct-2-ene
• 英文别名: 1-(8-Methyl-8-azabicyclo[3.2.1]oct-2-en-2-yl)propan-1-one
• CAS: 156038-49-2
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: NBLPKIOUMFCZNO-UHFFFAOYSA-N

物化性质

• 沸点：
  283.3±28.0 °C(predicted)
• 密度：
  1.035±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-methyl-2-propanoyl-8-azabicyclo<3.2.1>oct-2-ene 在 copper(I) bromide dimethylsulfide complex 、 一氯化碘 作用下， 生成 1-[(1R,2S,3S,5S)-3-(3-iodophenyl)-8-methyl-8-azabicyclo[3.2.1]octan-2-yl]propan-1-one
  参考文献：
  名称：

  Synthesis of iodinated 3β-aryltropanes with selective binding to either the dopamine or serotonin transporters

  摘要：

  Iodinated 3beta-aryltropanes functionalized appropriately at the 2beta-, 8- and aryl positions display selective binding to either the dopamine or serotonin transporters. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00048-3
• 作为产物：
  描述：

  5-己烯-3-酮 在 RhCl(PPh₃)3 rhodium(II) octanoate 、 4-乙酰氨基苯磺酰叠氮 、 氢气 、 sodium cyanoborohydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 乙醇 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 25.0 ℃ 、310.27 kPa 条件下， 反应 14.25h， 生成 8-methyl-2-propanoyl-8-azabicyclo<3.2.1>oct-2-ene
  参考文献：
  名称：

  Synthesis of 2.beta.-Acyl-3.beta.-aryl-8-azabicyclo[3.2.1]octanes and Their Binding Affinities at Dopamine and Serotonin Transport Sites in Rat Striatum and Frontal Cortex

  摘要：

  A novel entry to tropane analogs of cocaine was developed on the basis of the reaction of rhodium-stabilized vinylcarbenoids with pyrroles. These analogs were tested:in binding to dopamine and serotonin (5-HT) transporters in:membranes from rat striatum and frontal cortex. In all the analogs, the aryl group at the 3-position was directly bound to the tropane ring (as in WIN-35,428), and methyl or ethyl ketone moieties were present at the a-position instead of the typical ester group. The series of analogs containing a 2-naphthyl group at the 3-position were most potent, with K-i values < 1 nM in binding to both dopamine and 5-HT transporters. Although the unsubstituted 2-naphthyl analog was nonselective at dopamine and 5-HT transport sites, other compounds:were selective for either site. In general, compounds with relatively small substituents on the aromatic moiety (such as p-methyl or p-fluoro) were relatively selective for the dopamine transporters, while a p-isopropylphenyl derivative was selective:for the 5-HT transport sites. This latter compound represents the first N-methyltropane derivative specific for 5-HT transporters. Resolution of two of the most significant analogs was achieved by HPLC on a chiral stationary phase; the active enantiomer of a 2-naphthyl analog exhibited K-i values of <0.1 nM at both dopamine and 5-HT transporter sites.

  DOI：

  10.1021/jm00035a005

文献信息

• Synthesis of 3β-Aryl-8-azabicyclo[3.2.1]octanes with High Binding Affinities and Selectivities for the Serotonin Transporter Site
  作者：Huw M. L. Davies、Lisa A. Kuhn、Craig Thornley、Julius J. Matasi、Tammy Sexton、Steven R. Childers

  DOI：10.1021/jm9600508

  日期：1996.1.1

  A novel entry to tropane analogs of cocaine was developed based on the reaction of rhodium-stabilized vinylcarbenoids with pyrroles. These analogs were tested in binding to dopamine, serotonin (5-HT), and norepinephrine transporters in membranes from rat striatum and frontal cortex. In all the analogs, the aryl group at the 3 position was directly bound to the tropane ring and an ethyl ketone moiety

  基于铑稳定的乙烯基类胡萝卜素与吡咯的反应，开发了可卡因的托烷类似物的新型产品。测试了这些类似物与大鼠纹状体和额叶皮膜中的多巴胺，5-羟色胺（5-HT）和去甲肾上腺素转运蛋白的结合。在所有类似物中，在3位上的芳基直接与托烷环结合并且在2位上存在乙基酮部分。通过适当地修饰芳基和氮取代基，制备了高效的和5-HT选择性的托烷。最有效和选择性最大的化合物是3β-[4-（1-甲基乙烯基）苯基] -2β-丙酰基-8-氮杂双环[3.2.1]辛烷（13b），Ki为0。
• Synthesis and monoamine transporter affinity of 3β-(4-(2-pyrrolyl)phenyl)-8-azabicyclo[3.2.1]octanes and 3β-(5-Indolyl)-8-azabicyclo[3.2.1]octanes
  作者：Huw M.L Davies、Pingda Ren、Norman Kong、Tammy Sexton、Steven R Childers

  DOI：10.1016/s0960-894x(00)00701-0

  日期：2001.2

  3 beta-(5-Indolyl)-8-azabicyclo[3.2.1]octanes display potent binding affinity for both the dopamine and serotonin transporters, while certain 3 beta-(4-(2-pyrrolyl)phenyl)-8-azabicyclo[3.2.1]octanes selectively bind to the serotonin transporter. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Diastereoselective Kinetic Protonation of Exocyclic Enolates Derived from Bicyclic Ketones:  Control of Stereochemistry Mediated by Bridging Heteroatoms
  作者：Huw M. L. Davies、L. Mark Hodges、Timothy M. Gregg

  DOI：10.1021/jo0158940

  日期：2001.11.1