1-phenylethyl-1,2,3,4-tetrahydroisoquinoline | 84010-75-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 1-phenylethyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: (S)-1-β-phenylethyl-1,2,3,4-tetrahydro-isoquinoline；(S)-1-phenethyl-1,2,3,4-tetrahydroisoquinoline；(S)-1,2,3,4-tetrahydro-1-phenethylisoquinoline；(1S)-1-(2-phenylethyl)-1,2,3,4-tetrahydroisoquinoline
• CAS: 84010-75-3
• 化学式: C₁₇H₁₉N
• 分子量: 237.345
• InChiKey: UKUJIVVXTYWNIO-KRWDZBQOSA-N

物化性质

• 沸点：
  377.2±11.0 °C(Predicted)
• 密度：
  1.029±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3,4-二氢异喹啉-2(1h)-甲醛 在 正丁基锂 、 triethyloxonium fluoroborate 、 一水合肼 、 溶剂黄146 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.08h， 生成 1-phenylethyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  α-氨基碳负离子的对映选择性烷基化：（S）-1-烷基-1，2，3，4四氢异喹啉的合成

  摘要：

  一系列转化为1、2、3、4-四氢异喹啉的甲am衍生物的手性氨基醇被评估为手性偶极稳定的阴离子。用卤代烷进行烷基化可得到1-烷基-1、2、3、4-四氢异喹啉，它们的收率和对映体纯度都很高。

  DOI：

  10.1016/s0040-4020(01)82421-2

文献信息

• Asymmetric synthesis of isoquinoline alkaloids
  作者：A.l. Meyers、Daniel A. Dickman、Michael Boes

  DOI：10.1016/s0040-4020(01)87686-9

  日期：1987.1

  to variously substituted tetrahydroisoquinolines, allows asymmetric C-C bond forming reactions to occur α- to the amino group. In this manner, a wide variety of (S)-1-alkyl-1,2,3,4-tetrahydroisoquinolines were constructed in > 90% enantiomeric excess. Choosing the proper substituents and skeletal features, an efficient entry into the benzylisoquinoline, tetrahydroprotoberberine, aporphine, and isopavine

  通过使用固定在各种取代的四氢异喹啉上的手性甲am，可以使氨基的α-发生不对称的CC键形成反应。以这种方式，以＞ 90％的对映体过量构造了各种各样的（S）-1-烷基-1,2,3,4-四氢异喹啉。选择合适的取代基和骨架特征，可以有效地进入苄基异喹啉，四氢小ber碱，阿福啡和异戊烷类生物碱。
• Reissert-like Alkenylation of Azaaromatic Compounds with Alkenylzirconocene Chloride Complexes
  作者：Akio Saito、Yuji Hanzawa、Kohei Sudo、Koichi Iimura、Miki Hayashi

  DOI：10.3987/com-12-s(n)7

  日期：——

  Reissert-like alkenylation of azaaromatic compounds by the use of alkenylzirconocene chloride as a nucleophile was carried out in the presence of a stoichiometric amount of ClCO2Et. The regioselectivity of the nucleophilic attack depends on reacting heterocycles, solvent, and the presence of copper catalyst. Thus, the reaction of quinoline derivatives with alkenylzirconocene chloride in MeNO2 proceeded in a preferential 1,2-addition manner to give N-ethoxycarbonyl-2-alkenyl-1,2-dihydroquinolines, and the reaction of pyridine in CH2Cl2 under Cu(I)-catalyzed conditions proceeded in a 1,4-addition manner to give N-ethoxycarbonyl-4-alkenyl-1,4-dihydropyridine. The alkenylation of 3,4-dihydroisoquinoline with alkenylzirconocene chloride was also carried out in an enantioselective manner under Cu(I)/chiral Box-catalyzed conditions to give alkenylated tetrahydroisoquinoline compound (75%ee).
• Cu ^II /TEMPO‐Catalyzed Enantioselective C(sp ³ )–H Alkynylation of Tertiary Cyclic Amines through Shono‐Type Oxidation
  作者：Pei‐Sen Gao、Xin‐Jun Weng、Zhen‐Hua Wang、Chao Zheng、Bing Sun、Zhi‐Hao Chen、Shu‐Li You、Tian‐Sheng Mei

  DOI：10.1002/anie.202005099

  日期：2020.8.24

  AbstractA novel strategy for asymmetric Shono‐type oxidative cross‐coupling has been developed by merging copper catalysis and electrochemistry, affording C1‐alkynylated tetrahydroisoquinolines with good to excellent enantioselectivity. The use of TEMPO as a co‐catalytic redox mediator is crucial not only for oxidizing a tetrahydroisoquinoline to an iminium ion species but also for decreasing the oxidation potential of the reaction. A novel bisoxazoline ligand is also reported.
• Asymmetric alkylation of α-amino carbanions. An enantioselective synthesis of (S)-1-alkyl-1,2,3,4-tetrahydroisoquinolines
  作者：A. I. Meyers、Lelia M. Fuentes

  DOI：10.1021/ja00339a022

  日期：1983.1
• Meyers, Albert I.; Boes, Michael; Dickman, Daniel A., Angewandte Chemie, 1984, vol. 96, # 6, p. 448 - 449
  作者：Meyers, Albert I.、Boes, Michael、Dickman, Daniel A.

  DOI：——

  日期：——