(2S)-N-(2-bromoprop-2-enyl)-N-[(4-oxocyclohex-1-enyl)methyl]tryptophan ethylene acetal methyl ester | 927421-82-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-N-(2-bromoprop-2-enyl)-N-[(4-oxocyclohex-1-enyl)methyl]tryptophan ethylene acetal methyl ester
• 英文别名: methyl (2S)-2-[2-bromoprop-2-enyl(1,4-dioxaspiro[4.5]dec-7-en-8-ylmethyl)amino]-3-(1H-indol-3-yl)propanoate
• CAS: 927421-82-7
• 化学式: C₂₄H₂₉BrN₂O₄
• 分子量: 489.409
• InChiKey: CQALEJQGIRXHOC-QFIPXVFZSA-N

物化性质

• 沸点：
  611.5±55.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-N-(2-bromoprop-2-enyl)-N-[(4-oxocyclohex-1-enyl)methyl]tryptophan ethylene acetal methyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 2-[2-(3-indolyl)-1(S)-methoxycarbonylethyl]-4-methylene-cis-perhydroisoquinolin-6-one ethylene acetal 、 2-[2-(3-indolyl)-1(S)-methoxycarbonylethyl]-4-methylene-trans-perhydroisoquinolin-6-one ethylene acetal
  参考文献：
  名称：

  Synthesis of trans-perhydroisoquinolines by 6-endo-trig radical cyclization of amino-tethered vinyl bromides and cyclohexenes

  摘要：

  Bu3SnH-promoted cyclization of several N-(2-bromoprop-2-enyl)-N-[(4-oxocyclohex-l-enyl)methyl]alkylamines is reported. It has been found that the generated vinyl radicals evolve through a 6-endo-cyclization pathway giving rise to the corresponding 4,6-functionalized perhydroisoquinolines in a prevalent trans-relative configuration. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.087
• 作为产物：
  描述：

  1-甲氧基-4-(羟甲基)-1,4-环己二烯 在 TEA 、 三氟化硼乙醚 、 sodium carbonate 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 25.5h， 生成 (2S)-N-(2-bromoprop-2-enyl)-N-[(4-oxocyclohex-1-enyl)methyl]tryptophan ethylene acetal methyl ester
  参考文献：
  名称：

  Synthesis of trans-perhydroisoquinolines by 6-endo-trig radical cyclization of amino-tethered vinyl bromides and cyclohexenes

  摘要：

  Bu3SnH-promoted cyclization of several N-(2-bromoprop-2-enyl)-N-[(4-oxocyclohex-l-enyl)methyl]alkylamines is reported. It has been found that the generated vinyl radicals evolve through a 6-endo-cyclization pathway giving rise to the corresponding 4,6-functionalized perhydroisoquinolines in a prevalent trans-relative configuration. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.087

文献信息

• Synthesis of trans-perhydroisoquinolines by 6-endo-trig radical cyclization of amino-tethered vinyl bromides and cyclohexenes
  作者：Josefina Quirante、Xavier Vila、Laura Paloma、Josep M. Guiu、Josep Bonjoch

  DOI：10.1016/j.tet.2006.11.087

  日期：2007.2

  Bu3SnH-promoted cyclization of several N-(2-bromoprop-2-enyl)-N-[(4-oxocyclohex-l-enyl)methyl]alkylamines is reported. It has been found that the generated vinyl radicals evolve through a 6-endo-cyclization pathway giving rise to the corresponding 4,6-functionalized perhydroisoquinolines in a prevalent trans-relative configuration. (c) 2006 Elsevier Ltd. All rights reserved.