1,4-二甲基-3,4-二氢异喹啉 | 59261-37-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢异喹啉
• 中文名称: 1,4-二甲基-3,4-二氢异喹啉
• 英文名称: 1,4-dimethyl-3,4-dihydroisoquinoline
• 英文别名: 1,4-dimethyl-3,4-dihydro-isoquinoline；1,4-Dimethyl-3,4-dihydro-isochinolin
• CAS: 59261-37-9
• 化学式: C₁₁H₁₃N
• mdl: MFCD09833181
• 分子量: 159.231
• InChiKey: BEGGTDKXWFOTME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  1,4-二甲基-3,4-二氢异喹啉 在 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 生成 1,1,1-trifluoro-2-methyl-3-(4-methyl-3,4-dihydroisoquinolin-1-yl)propan-2-ol
  参考文献：
  名称：

  格氏试剂介导的二氢异喹啉酰胺中三氟乙酰基的重排，以提供叔三氟甲基甲醇

  摘要：

  用不同的格氏试剂处理二氢异喹啉2的三氟乙酰酰胺，通过促进叔甲醇向酰胺2的β-碳加成，得到叔三氟甲基羰基化合物4。基于已证实的乙烯基类酰胺3的形成，该转化可能通过独特的酰基重排至该酰胺的β-碳并随后亲核添加格氏试剂来进行。考虑到该反应的合成实用性和新颖性，这项工作可能会为在环烯酰胺系统上合成重要的叔三氟甲基碳氢化合物药用开辟新的途径。

  DOI：

  10.1039/c7ob03079g
• 作为产物：
  描述：

  N-烯丙基乙酰胺 在 phosphorus pentoxide 、 xylene 、 三氯氧磷 作用下， 生成 1,4-二甲基-3,4-二氢异喹啉
  参考文献：
  名称：

  Saha et al., Science and Culture, 1952, vol. 18, p. 152

  摘要：

  DOI：

文献信息

• Succinct Syntheses of Methopholine, (±)‐Homolaudanosine, and (±)‐Dysoxyline via Metal‐free One‐Pot Double Alkylation on 1‐Methyl‐3,4‐dihydroisoquinolines
  作者：Raghavendra Achary、Seulgi Kim、Yuri Choi、Gangadhar Rao Mathi、Hyun Jin Kim、Jong Yeon Hwang、Pilho Kim

  DOI：10.1002/bkcs.11677

  日期：2019.3

  A mild one‐pot and metal‐free condition was discovered to implement two different alkyl groups chemoselectively on 1‐methyl‐3,4‐dihydroisoquinoline (1‐Me‐DHIQ), one at the nitrogen another at the C1‐methyl group. This chemistry is compatible with various DHIQs as well as alkyl halides. Application of this chemistry facilitated the concise syntheses of methopholine, (±)‐homolaudanosine, and (±)‐dysoxyline

  发现一种温和的单锅无金属条件可以在1-甲基-3,4-二氢异喹啉（1-Me-DHIQ）上化学选择性地实现两个不同的烷基，一个在氮上，另一个在C1-甲基上。这种化学性质与各种DHIQ和烷基卤化物相容。该化学方法的应用促进了甲氧茶碱，（±）-高麦芽糖苷和（±）-二羟基苯酚的简明合成，从6,7-二甲氧基-1-Me-DHIQ只需两个步骤。
• Spaeth et al., Chemische Berichte, 1930, vol. 63, p. 134,136
  作者：Spaeth et al.

  DOI：——

  日期：——
• Thermal electrocyclic reactions of 2-aza-1,3-butadiene derivatives. A new N-heterocyclic annelation
  作者：C. K. Govindan、Grant Taylor

  DOI：10.1021/jo00174a036

  日期：1983.12
• Conformational Analysis. 50. <i>C</i>-Methyl-1,2,3,4-tetrahydroisoquinolines
  作者：Edward M. Olefirowicz、Ernest L. Eliel

  DOI：10.1021/jo971257r

  日期：1997.12.1

  Conformational equilibria in 1-, 3-, and 4-methyl-1,2,3,4-tetrahydroisoquinolines (THIQs) and the diastereomeric pairs of their 1,3- and 1,4-dimethyl homologs have been determined by measurement of H-3/H-4(trans) coupling constants and have been confirmed by molecular mechanics [MMP2(85]) calculations. The experimental -Delta G degrees values (a --> e) for the monomethyl compounds (computed values in parentheses) in kcal mol(-1) are Me-1, 0.56 (0.46); Me-3, 1.63 (1.53); and Me-4, -0.32 (-0.22). Agreement of experimental and calculated values is very goad as is the additivity of values for the dimethyl compounds (Table 1). Values for the corresponding hydrochlorides are Me-1, 0.19 (-0.34); Me-3, 1.15 (1.46); and Me-4, 0.35 (0.10) kcal mol(-1). The less than satisfactory agreement of experimental with computed data here is probably due to neglect of solvation. The very small or negative Delta G degrees values for Me-1 and Me-4 were ascribed not only to the pseudoaxial (rather than axial) nature of Me(ax) and the absence of a syn-axial hydrogen on the side of the benzene ring but also to a peri interaction with H(8) and H(5), respectively, destabilizing equatorial methyl at positions 1 and 4. This was confirmed by comparing computed conformational energy values with values at corresponding positions in Delta(3,4)-tetrahydropyridines (THPs). While Delta G degrees in the two series is the same for Me-3 (THIQ numbering), that for Me-1 and Me-4 is considerably smaller in the THIQ than in the THP series which latter is devoid of peri hydrogens.
• Synthesis and characterization of a diaziridinium ion. Conversion of 3,4-dihydroisoquinolines to 4,5-dihydro-3H-benzo[2,3]diazepines via a formal N-insertion process
  作者：Julia M. Allen、Tristan H. Lambert

  DOI：10.1016/j.tet.2014.03.015

  日期：2014.7