1-(4-methoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline | 1620820-59-8

• 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-(4-methoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-(4-methoxyphenyl)-2-methyl-3,4-dihydro-1H-isoquinoline
• CAS: 1620820-59-8
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: BROHBYNENSOOKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline 在 N-溴代丁二酰亚胺(NBS) 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 sodium carbonate 、 (S)-(-)-[(5,6),(5',6')-双(乙烯二氧)联苯-2,2'-基]二苯基磷 、 氢气 作用下， 以 1,2-二氯乙烷 为溶剂， 20.0~30.0 ℃ 、3.45 MPa 条件下， 反应 24.33h， 以91%的产率得到(R)-1-(4-methoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Concise Redox Deracemization of Secondary and Tertiary Amines with a Tetrahydroisoquinoline Core via a Nonenzymatic Process

  摘要：

  A concise deracemization of racemic secondary and tertiary amines with a tetrahydroisoquinoline core has been successfully realized by orchestrating a redox process consisted of N-bromosuccinimide oxidation and iridum-catalyzed asymmetric hydrogenation. This compatible redox combination enables one-pot, single-operation deracemization to generate chiral 1-substituted 1,2,3,4-tetrahydroisoquinolines with up to 98% ee in 93% yield, offering a simple and scalable synthetic technique for chiral amines directly from racemic starting materials.

  DOI：

  10.1021/jacs.5b06659
• 作为产物：
  描述：

  2-甲基-1,2,3,4-四氢异喹啉 、 对氟苯甲醚 在 三氟化硼乙醚 、 仲丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 1.75h， 以35%的产率得到1-(4-methoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Nucleophilic Addition of Lewis Acid Complexed α-Amino Carbanions to Arynes: Synthesis of 1-Aryl-N-methyl-1,2,3,4-tetrahydroisoquinolines

  摘要：

  The direct C-1 arylation of N-methyl-1,2,3,4-tetrahydroisoquinolines via coupling of alpha-amino carbanions derived from Lewis acid complexed tetrahydroisoquinolines and in situ generated arynes is described. This process provides an easy access to the title compounds and a new synthetic route to (+/-)-cryptostyline alkaloids.

  DOI：

  10.1055/s-0033-1341239

文献信息

• Transition-Metal-Free Arylation of N-Alkyl-tetrahydroisoquinolines under Oxidative Conditions: A Convenient Synthesis of C1-Arylated Tetrahydro­isoquinoline Alkaloids
  作者：Kamal Singh、Satinder Kessar、Paramjit Singh、Pushpinder Singh、Manjot Kaur、Aanchal Batra

  DOI：10.1055/s-0034-1378337

  日期：——

  Abstract A simple protocol for the C1 arylation of tetrahydroisoquinolines with aryl Grignard reagents via diethyl azodicarboxylate (DEAD) mediated oxidative C–H activation under metal-free conditions has been developed. The target compounds, including some naturally occurring alkaloids, were obtained in moderate to good yields. A simple protocol for the C1 arylation of tetrahydroisoquinolines with

  摘要 已经开发了一种在无金属条件下通过偶氮二羧酸二乙酯（DEAD）介导的氧化CH活化四氢异喹啉与芳基格氏试剂进行C1芳基化的简单协议。以中等至良好的产率获得了目标化合物，包括一些天然存在的生物碱。 已经开发了一种在无金属条件下通过偶氮二羧酸二乙酯（DEAD）介导的氧化CH活化四氢异喹啉与芳基格氏试剂进行C1芳基化的简单协议。以中等至良好的产率获得了目标化合物，包括一些天然存在的生物碱。
• Oxidative cyanation of tertiary amines for facile synthesis of tetrahydroisoquinolines with quaternary centers
  作者：Yue Ji、Xue Zhang、Ya Wu、Ze-Lin Dang、Wei-Wei Han、Si-Chang Wang、San-Bao Dong、Qun-Zheng Zhang

  DOI：10.1016/j.tetlet.2022.154175

  日期：2022.11

  facile and efficient synthesis of tetrahydroisoquinolines with quaternary centers has been successfully realized by orchestrating a sequential process consisted of N-bromosuccinimide oxidation and cyanation of tertiary amines. This compatible combination protocol enables one-pot synthesis of α-cyano tetrahydroisoquinolines containing a quaternary center with up to 99% yield.

  通过协调由N-溴代琥珀酰亚胺氧化和叔胺氰化组成的顺序过程，已经成功地实现了具有季中心的四氢异喹啉的简便有效合成。这种兼容的组合方案能够一锅合成含有季铵中心的 α-氰基四氢异喹啉，产率高达 99%。
• 一种α,α-二取代四氢异喹啉类化合物的合成方法
  申请人：西安石油大学

  公开号：CN114516835B

  公开（公告）日：2023-08-15

  本发明提供一种α，α‑二取代四氢异喹啉化合物的合成方法，将式(1)所示的四氢异喹啉类化合物加至有机溶剂中，并加入氧化剂和碱性添加剂，进行氧化反应，随后再加入三甲基氰硅烷和有机溶剂，进行亲核加成反应，得到式(2)α，α‑二取代四氢异喹啉类化合物；其中，Rx为‑H、‑F、‑Cl、‑CH3和‑OCH3中的一种或两种；R1和R2各自独立的为‑H、‑CH3或‑OCH3；所述氧化剂为N‑溴代丁二酰亚胺、N‑碘代丁二酰亚胺、N‑氯代丁二酰亚胺、二溴海因或三氯异氰尿酸。本发明方法能实现α，α‑二取代四氢异喹啉类化合物的合成，反应条件温和且产物收率高。
• Concise Redox Deracemization of Secondary and Tertiary Amines with a Tetrahydroisoquinoline Core via a Nonenzymatic Process
  作者：Yue Ji、Lei Shi、Mu-Wang Chen、Guang-Shou Feng、Yong-Gui Zhou

  DOI：10.1021/jacs.5b06659

  日期：2015.8.26

  A concise deracemization of racemic secondary and tertiary amines with a tetrahydroisoquinoline core has been successfully realized by orchestrating a redox process consisted of N-bromosuccinimide oxidation and iridum-catalyzed asymmetric hydrogenation. This compatible redox combination enables one-pot, single-operation deracemization to generate chiral 1-substituted 1,2,3,4-tetrahydroisoquinolines with up to 98% ee in 93% yield, offering a simple and scalable synthetic technique for chiral amines directly from racemic starting materials.
• Nucleophilic Addition of Lewis Acid Complexed α-Amino Carbanions to Arynes: Synthesis of 1-Aryl-N-methyl-1,2,3,4-tetrahydroisoquinolines
  作者：Kamal Singh、Paramjit Singh、Esha Sharma、Yadwinder Deol

  DOI：10.1055/s-0033-1341239

  日期：——

  The direct C-1 arylation of N-methyl-1,2,3,4-tetrahydroisoquinolines via coupling of alpha-amino carbanions derived from Lewis acid complexed tetrahydroisoquinolines and in situ generated arynes is described. This process provides an easy access to the title compounds and a new synthetic route to (+/-)-cryptostyline alkaloids.