N-<2-(3,4-dimethoxyphenyl)-ethyl>-5-hydroxypentanamide | 15889-91-5

• 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: N-<2-(3,4-dimethoxyphenyl)-ethyl>-5-hydroxypentanamide
• 英文别名: N-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxypentanamide
• CAS: 15889-91-5
• 化学式: C₁₅H₂₃NO₄
• 分子量: 281.352
• InChiKey: LQWFQKYRFRVGGI-UHFFFAOYSA-N

物化性质

• 熔点：
  70-71 °C
• 沸点：
  497.8±45.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<2-(3,4-dimethoxyphenyl)-ethyl>-5-hydroxypentanamide 在 正丁基锂 、 草酰氯 、 碘苯二乙酸 、 二甲基亚砜 、 三乙胺 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 11.17h， 生成 (2SR,11bRS)-2-formyl-9,10-dimethoxy-1,2,3,6,7,11b-hexahydrobenzo[a]quinolizin-4-one
  参考文献：
  名称：

  Conjugate Additions of Sulfur-Stabilized Anions to Unsaturated Lactams. Synthesis of Polyfunctionalized Benzo[a]quinolizinone Systems

  摘要：

  Conjugate addition reactions of sulfur-stabilized nucleophiles to the delta-lactam unit of tetrahydrobenzo[a]benzoquinolizines have been studied. The stereochemical outcome of the conjugate addition reaction depends on the nature of the substituent at the angular position, thus 2,11b-cis or 2,11b-trans diastereomers could be obtained selectively. The tandem conjugate addition-alkylation also takes place in good yields and with high diastereoselectivity. The polyfunctionalized hexahydrobenzo[a]quinolizinone systems obtained could be further elaborated toward emetine-like structures.

  DOI：

  10.1021/jo060903w
• 作为产物：
  描述：

  3,4-二甲氧基苯乙胺 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 16.0h， 生成 N-<2-(3,4-dimethoxyphenyl)-ethyl>-5-hydroxypentanamide
  参考文献：
  名称：

  Conjugate Additions of Sulfur-Stabilized Anions to Unsaturated Lactams. Synthesis of Polyfunctionalized Benzo[a]quinolizinone Systems

  摘要：

  Conjugate addition reactions of sulfur-stabilized nucleophiles to the delta-lactam unit of tetrahydrobenzo[a]benzoquinolizines have been studied. The stereochemical outcome of the conjugate addition reaction depends on the nature of the substituent at the angular position, thus 2,11b-cis or 2,11b-trans diastereomers could be obtained selectively. The tandem conjugate addition-alkylation also takes place in good yields and with high diastereoselectivity. The polyfunctionalized hexahydrobenzo[a]quinolizinone systems obtained could be further elaborated toward emetine-like structures.

  DOI：

  10.1021/jo060903w

文献信息

• Enantioselective synthesis of some tetrahydroisoquinoline and tetrahydro-β-carboline alkaloids
  作者：Joanna Szawkało、Stefan J. Czarnocki、Anna Zawadzka、Krystyna Wojtasiewicz、Andrzej Leniewski、Jan K. Maurin、Zbigniew Czarnocki、Józef Drabowicz

  DOI：10.1016/j.tetasy.2007.01.014

  日期：2007.2

  Four alkaloids: (R)-(+)-cryspine A 5, (R)-(+)-octahydroindolo[2,3-a]quinolizidine 8, (R)-(+)-harmicine 19 and (R)-(+)-desbromoarborescidine 22 were prepared via the asymmetric transfer hydrogenation reaction of a prochiral enamine (iminium salt). The enantiomeric excesses of the isolated alkaloids were determined from their 1H NMR spectra measured in the presence of (+)-(R)-tert-butylphenylphosphinothio(seleno)ic

  四种生物碱：（R）-（+）-地平A 5，（R）-（+）-八氢吲哚并[2,3- a ]喹唑烷8，（R）-（+）-毒品19和（R）-（通过前手性烯胺（亚胺盐）的不对称转移氢化反应制备了+）-去溴阿糖胞苷22。根据在（+）-（R）-叔存在下测得的1 H NMR光谱确定分离出的生物碱的对映体过量-丁基苯基膦硫基（硒）酸作为手性溶剂。在所有情况下，通过X射线晶体学证实了新产生的立体碳原子上的绝对构型。
• Photosolvolysis of Bridgehead Quaternary Ammonium Salts. III. Synthesis of Some 3-Benzazecine, 1H-2,6-Benzoxazecine and 2H-3,6-Benzoxazecine Derivatives and a 2H-1,4-Oxazocine Derivative
  作者：JB Bremner、KN Winzenberg

  DOI：10.1071/ch9851591

  日期：——

  Photosolvolysis of a mixture of cis - and trans-9,10-dimethoxy-5-methyl- 1,3,4,6,7,11b-hexahydro-2H-benzo[a] quinolizinium iodide (2) in methanol gave, after workup, a very low yield of 8,10,11-trimethoxy-3-methyl- 1,2,3,4,5,6,7,8-octahydro-3-benzazecine (3a). Similarly 1,10,11 trimethoxy-6-methyl-3,4,5,6,7,8-hexahydro-1H-2,6-benzoxazecine (8a) and 1,10,11-trimethoxy-6-methyl-1,4,5,6,7,8-hexahydro-2H-3,6-benzoxazecine (16a) were obtained in fair and low yields respectively from the N- methyl tetrahydro-2H,6H-[1,3] oxazino [2,3-a] isoquinolinium (7a) and hexahydro [1,4] oxazino [3,4-a] isoquinolinium (15) iodide precursors; a 1- methyl derivative (8b) of (8a) was also prepared. The ring-opened products 3-[N-2-(4,5-dimethoxy-2-dimethoxymethyl)-phenyl}ethyl-N-methyl]aminopropan-1-ol (9a) and 3-[N-2-(4,5-dimethoxy-2-1′,1′- dimethoxyethyl )-phenyl}ethyl-N-methyl]aminopropan-1-ol (9b) were also obtained from the [1,3] oxazino [2,3-a]- isoquinolinium salt derivatives. Photolysis of (2) and 9,10-dimethoxy-5-methyl-1,3,4,6,7,11b-hexa-hydro[1,4] oxazino [3,4-a] isoquinolinium iodide (15) in acidified aqueous solution afforded, after workup, the benzazecin-8-ol (3b) and hexahydro-2H-3,6-benzoxazecin-1-ol (16b) products respectively, but again in very low yield. Some mechanistic rationalizations of these results are given.Photosolvolysis of 7a-(3,4-dimethoxy)phenyl-4-methyl-2,3,5,6,7,7a- hexahydropyrrolo [2,1-b] oxa-zolium iodide (22) in methanol afforded a high yield of 8-methoxy-4-methyl-8-(3,4-dimethoxy)-phenyl-3,4,5,6,7,8- hexahydro-2H-1,4-oxazocine (24) in a new ring-destruction approach to this ring system. From 13C n.m.r . data, the twist-boat-chair conformation was tentatively assigned to (24) in (D)chloroform solution.

  在甲醇中对顺式和反式-9,10-二甲氧基-5-甲基-1,3,4,6,7,11b-六氢-2H-苯并[a]喹嗪碘化物（2）的混合物进行光酵解，经过加工后得到了产率极低的 8,10,11-三甲氧基-3-甲基-1,2,3,4,5,6,7,8-八氢-3-苯并氮杂嗪（3a）。同样，1,10,11-三甲氧基-6-甲基-3,4,5,6,7,8-六氢-1H-2,6-苯并噁嗪（8a）和 1,10,11-三甲氧基-6-甲基-1,4,5,6,7,8-六氢-2H-3、碘化 N-甲基四氢-2H,6H-[1,3] 恶嗪并[2,3-a] 异喹啉鎓（7a）和六氢[1,4] 恶嗪并[3,4-a] 异喹啉鎓（15）的前体，分别以一般和低产率获得了 6-苯并恶嗪（16a）；还制备了 (8a) 的 1- 甲基衍生物 (8b)。开环产物 3-[N-2-（4,5-二甲氧基-2-二甲氧基甲基）-苯基}乙基-N-甲基]氨基丙-1-醇（9a）和 3-[N-2-（4,5-二甲氧基-2-1′、1′-二甲氧基乙基）-苯基}乙基-N-甲基]氨基丙-1-醇（9b）。在酸化水溶液中光解 (2) 和 9,10-二甲氧基-5-甲基-1,3,4,6,7,11b-六氢[1,4]恶嗪并[3,4-a]异喹啉碘化物 (15)，分别得到苯并噻嗪-8-醇 (3b) 和六氢-2H-3,6-苯并恶嗪-1-醇 (16b)，但产率同样很低。对这些结果 这些结果给出了一些机理上的合理解释。在甲醇中对 7a-(3,4-二甲氧基)苯基-4-甲基-2,3,5,6,7,7a-六氢吡咯并[2,1-b] 氧杂唑鎓碘化物（22）进行光解，可得到高产率的 8-甲氧基-4-甲基-8-(3,4-二甲氧基)-苯基-2,3,5,6,7,7a-六氢吡咯并[2,1-b] 氧杂唑鎓碘化物（23）、4-dimethoxy)-phenyl-3,4,5,6,7,8- hexahydro-2H-1,4-oxazocine (24) 的高产率。根据 13C n.m.r .数据，(24) 在 (D)chloroform 溶液中的扭船椅构象被初步确定。
• Asymmetric Synthesis of Fused-Ring Tetrahydroisoquinolines and Tetrahydro-β-carbolines from 2-Arylethylamines via a Chemoenzymatic Approach
  作者：Linsong Yang、Jianjiong Li、Zefei Xu、Peiyuan Yao、Qiaqing Wu、Dunming Zhu、Yanhe Ma

  DOI：10.1021/acs.orglett.2c02466

  日期：2022.9.16

  While chiral fused-ring tetrahydroisoquinoline (THIQ) and tetrahydro-β-carboline (THβC) scaffolds have attracted considerable interest due to their wide spectrum of biological activities, the synthesis of optically pure chiral fused-ring THIQs and THβCs remains a challenging task. Herein, a group of active imine reductases were identified to convert the imine precursors into the corresponding enantiocomplementary

  虽然手性稠环四氢异喹啉 (THIQ) 和四氢-β-咔啉 (THβC) 支架因其广泛的生物活性而引起了相当大的兴趣，但合成光学纯的手性稠环 THIQs 和 THβCs 仍然是一项具有挑战性的任务。本文鉴定了一组活性亚胺还原酶，将亚胺前体转化为具有高对映选择性和转化率的相应的对映互补稠环 THIQ 和 THβC，建立了一种从 2-芳基乙胺制备稠环生物碱的高效绿色化学酶法。
• Bremner, John B.; Jaturonrusmee, Wasna, Australian Journal of Chemistry, 1991, vol. 44, p. 135 - 141
  作者：Bremner, John B.、Jaturonrusmee, Wasna

  DOI：——

  日期：——
• Conjugate Additions of Sulfur-Stabilized Anions to Unsaturated Lactams. Synthesis of Polyfunctionalized Benzo[<i>a</i>]quinolizinone Systems
  作者：Eva García、Esther Lete、Nuria Sotomayor

  DOI：10.1021/jo060903w

  日期：2006.9.1

  Conjugate addition reactions of sulfur-stabilized nucleophiles to the delta-lactam unit of tetrahydrobenzo[a]benzoquinolizines have been studied. The stereochemical outcome of the conjugate addition reaction depends on the nature of the substituent at the angular position, thus 2,11b-cis or 2,11b-trans diastereomers could be obtained selectively. The tandem conjugate addition-alkylation also takes place in good yields and with high diastereoselectivity. The polyfunctionalized hexahydrobenzo[a]quinolizinone systems obtained could be further elaborated toward emetine-like structures.