2-Propionyl-8-aza-bicyclo[3.2.1]octa-2,6-diene-8-carboxylic acid tert-butyl ester | 155930-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 2-Propionyl-8-aza-bicyclo[3.2.1]octa-2,6-diene-8-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 2-propanoyl-8-azabicyclo[3.2.1]octa-2,6-diene-8-carboxylate；tert-butyl 2-propanoyl-8-azabicyclo[3.2.1]octa-2,6-diene-8-carboxylate
• CAS: 155930-75-9
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: ALZFJRUQHJEDIV-UHFFFAOYSA-N

物化性质

• 沸点：
  381.8±42.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Propionyl-8-aza-bicyclo[3.2.1]octa-2,6-diene-8-carboxylic acid tert-butyl ester 在 (PPh₃)RhCl 、 氢气 、 sodium cyanoborohydride 、 三氟乙酸 作用下， 生成 8-methyl-2-propanoyl-8-azabicyclo<3.2.1>oct-2-ene
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(00)00701-0
• 作为产物：
  描述：

  5-己烯-3-酮 在 rhodium(II) octanoate 、 4-乙酰氨基苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 正己烷 、 乙腈 为溶剂， 反应 1.5h， 生成 2-Propionyl-8-aza-bicyclo[3.2.1]octa-2,6-diene-8-carboxylic acid tert-butyl ester
  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

• Cation induced rearrangement of 8-azabicyclo[3.2.1]octa-2,6-dienes to 6-azabicyclo[3.2.1]oct-2-enes
  作者：Huw M.L Davies、Guoan Cao

  DOI：10.1016/s0040-4039(98)01221-0

  日期：1998.8

  Various electrophiles induce the rearrangement of 8-azabicyclo[3.2.1]octa-2,6-dienes to 6-azabicyclo[3.2.1]oct-2-enes.

  各种亲电试剂可将8-氮杂双环[3.2.1] octa-2,6-二烯重排为6-氮杂双环[3.2.1] oct-2-enes。
• 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
  作者：Huw M. L. Davies、Elie Saikali、Nicholas J. S. Huby、Vernon J. Gilliatt、Julius J. Matasi、Tammy Sexton、Steven R. Childers

  DOI：10.1021/jm00035a005

  日期：1994.4

  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.
• 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.