1-benzyl-2-formyl-1,2,3,4-tetrahydroisoquinoline | 138967-33-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1-benzyl-2-formyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-phenylmethy-3,4-dihydro-1H-isoquinoline-2-carboxaldehyde；1-benzyl-3,4-dihydro-1H-isoquinoline-2-carbaldehyde
• CAS: 138967-33-6
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: NJHWZUPAFFNPCC-UHFFFAOYSA-N

物化性质

• 熔点：
  80-81 °C
• 沸点：
  439.4±34.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-benzyl-2-formyl-1,2,3,4-tetrahydroisoquinoline 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到1-苄基-2-甲基-1,2,3,4-四氢异喹啉
  参考文献：
  名称：

  A Highly Efficient Synthesis of 1-Methyl-, 1-Benzyl-, and 1-Phenyl-1,2,3,4-tetrahydroisoquinolines by a Modified Pummerer Reaction

  摘要：

  DOI：

  10.3987/com-97-s70
• 作为产物：
  描述：

  N-(1,2-diphenylethyl)-N-(2-phenylsulfanylethyl)formamide 在 sodium tetrahydroborate 、 sodium periodate 、 三氟化硼乙醚 、 三氟乙酸酐 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 8.5h， 生成 1-benzyl-2-formyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  A Highly Efficient Synthesis of 1-Methyl-, 1-Benzyl-, and 1-Phenyl-1,2,3,4-tetrahydroisoquinolines by a Modified Pummerer Reaction

  摘要：

  DOI：

  10.3987/com-97-s70

文献信息

• Synthesis of benzyl substituted tetrahydropyridines and 1,2,3,4-tetrahydroisoquinolines via acid catalyzed cyclization of γ,δ-unsaturated N-formyl-N-styryl amines
  作者：Gerrit J. Meuzelaar、Leendert Maat、Roger A. Sheldon

  DOI：10.1016/s0040-4020(99)00136-2

  日期：1999.4

  Acid-catalyzed cyclization of N-(3-methylbut-3-enyl)-N-styrylformamides 1–3 in the presence of 9-BBN triflate gave access to 2-benzyl-1-formyl-4-methyl-1,2,5,6-tetrahydropyridines 4a–6a and minor amounts of the isomeric 1,2,3,6-tetrahydropyridines 4b–6b. Triflic acid catalyzed cyclization of N-2-(arylethyl)-N-styrylformamides 7, 8 gave the corresponding 1-benzyl-2-formyl-1,2,3,4-tetrahydroisoquinolines

  在存在9-BBN三氟甲磺酸酯的情况下，酸催化N-（3-甲基丁-3-烯基）-N-苯乙烯基甲酰胺1-3的环化反应，可得到2-苄基-1-甲酰基-4-甲基-1,2， 5,6-四氢吡啶4a-6a和少量的异构体1,2,3,6-四氢吡啶4b-6b。的三氟甲磺酸催化环化Ñ -2-（芳基乙基） - ñ -styrylformamides 7,8得到相应的1-苄基-2-甲酰基-1,2,3,4-四氢异喹啉9和10。
• Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells
  作者：Seikou Nakamura、Souichi Nakashima、Genzo Tanabe、Yoshimi Oda、Nami Yokota、Katsuyoshi Fujimoto、Takahiro Matsumoto、Rika Sakuma、Tomoe Ohta、Keiko Ogawa、Shino Nishida、Hisako Miki、Hisashi Matsuda、Osamu Muraoka、Masayuki Yoshikawa

  DOI：10.1016/j.bmc.2012.11.038

  日期：2013.2

  Methanolic extracts from the flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) were found to show inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the methanolic extracts, a new alkaloid, N-methylasimilobine N-oxide, was isolated together with eleven benzylisoquinoline alkaloids. The absolute stereostructure of the new alkaloid was determined from chemical and physicochemical evidence. Among the constituents isolated, nuciferine, N-methylasimilobine, (-)-lirinidine, and 2-hydroxy-1-methoxy-6a, 7-dehydroaporphine showed potent inhibition of melanogenesis. Comparison of the inhibitory activities of synthetic related alkaloids facilitated characterization of the structure-activity relationships of aporphine-and benzylisoquinoline-type alkaloids. In addition, 3-30 mu M nuciferine and N-methylasimilobine inhibited the expression of tyrosinase mRNA, 3-30 mu M N-methylasimilobine inhibited the expression of TRP-1 mRNA, and 10-30 mu M nuciferine inhibited the expression of TRP-2 mRNA. (C) 2012 Elsevier Ltd. All rights reserved.
• Structure-affinity relationships of berbines or 5,6,13,13a-tetrahydro-8H-dibenzo[a,g]quinolizines at α-adrenoceptors
  作者：G Memetzidis、JF Stambach、L Jung、C Schott、C Heitz、JC Stoclet

  DOI：10.1016/0223-5234(91)90195-s

  日期：1991.9

  The synthesis of some derivatives of tetrahydro-8H-dibenzo[a,g]quinolizines or berbines is described. A pharmacological study was carried out at alpha-1 and alpha-2-adrenoceptors using radioligand binding techniques. This study has shown that the aromatic ring A is responsible for the alpha-2-affinity of berbines. Furthermore, the aromatic ring D is important for alpha-1-affinity. However, in this case, it seems that the planarity of the molecule is a very important structural parameter for affinity. The role of the nitrogen atom is also discussed. A conformational analysis of the partial saturated berbines was established by a C-13 NMR study.