N-pivaloyl-1,2,3,4-tetrahydroisoquinoline | 76068-81-0

• 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: N-pivaloyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-(3,4-dihydroisoquinolin-2(1H)-yl)-2,2-dimethylpropan-1-one；2-(2,2-Dimethylpropanoyl)-1,2,3,4-tetrahydroisoquinoline；1-(3,4-dihydro-1H-isoquinolin-2-yl)-2,2-dimethylpropan-1-one
• CAS: 76068-81-0
• 化学式: C₁₄H₁₉NO
• mdl: MFCD01344856
• 分子量: 217.311
• InChiKey: HWSYMHFJGZIIOP-UHFFFAOYSA-N

物化性质

• 熔点：
  67-69 °C(Solv: hexane (110-54-3))
• 沸点：
  360.0±31.0 °C(Predicted)
• 密度：
  1.044±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  N-pivaloyl-1,2,3,4-tetrahydroisoquinoline 在 盐酸 、 正丁基锂 、 三乙胺 、 红铝 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 21.0h， 生成 1-(α-hydroxybenzhydryl)-1,2,3,4-tetrahydroisoquinoline hydrochloride
  参考文献：
  名称：

  Alkylation of the isoquinoline skeleton in the 1-position

  摘要：

  DOI：

  10.1016/s0040-4020(01)91914-3
• 作为产物：
  描述：

  三甲基乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 N-pivaloyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Direct Inter- and Intramolecular Addition of Amides to Arylalkenes Promoted by KOt-Bu/DMF

  摘要：

  Direct addition of tetrahydroisoquinoline derived amides to arylalkenes has been achieved in the presence of KOt-Bu/DMF. Both intermolecular and intramolecular reactions could occur in good yields. α-Amido alkyl radicals are proposed to be generated under the reaction conditions. The reaction is efficient for the synthesis of seven-membered nitrogen heterocycles. A homoprotoberberine was prepared conveniently via this method.

  DOI：

  10.1021/jo501179t

文献信息

• Rhodium-Catalyzed Oxidative Amidation of Sterically Hindered Aldehydes and Alcohols
  作者：Trang T. Nguyen、Kami L. Hull

  DOI：10.1021/acscatal.6b02541

  日期：2016.12.2

  has been developed with sterically hindered aldehydes and alcohols for the synthesis of amides containing a quaternary carbon at the α position. A variety of amine nucleophiles, both aliphatic and aromatic, are employed and afford the corresponding amides in good to excellent yields. Finally, mechanistic studies are performed to gain insight into both catalytic cycles.

  已经开发出铑与空间受阻的醛和醇催化的氧化酰胺化反应，以合成在α位含有季碳的酰胺。使用脂肪族和芳香族的多种胺亲核试剂，并以良好或优异的收率得到相应的酰胺。最后，进行机理研究以了解两个催化循环。
• SULFONE AMIDE LINKED BENZOTHIAZOLE INHIBITORS OF ENDOTHELIAL LIPASE
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20160326125A1

  公开（公告）日：2016-11-10

  The present invention provides compounds of Formula (I) as defined in the specification and compositions comprising any of such novel compounds. These compounds are endothelial lipase inhibitors which may be used medicaments.

  本发明提供了规范中定义的Formula (I)的化合物以及包含任何此类新化合物的组合物。这些化合物是内皮酶抑制剂，可用作药物。
• Overcoming solid handling issues in continuous flow substitution reactions through ionic liquid formation
  作者：Saeed K. Kashani、Ryan J. Sullivan、Mads Andersen、Stephen G. Newman

  DOI：10.1039/c8gc00618k

  日期：——

  the use of acid scavenging organic bases that generate low- to moderate-melting ionic liquids upon protonation. The application of these bases towards the most commonly run substitutions are demonstrated, enabling reactions to be run in flow without requiring additional equipment, specific solvents, or dilute reaction conditions to prevent clogging.

  诸如酰化，芳基化和烷基化之类的取代是构建复杂分子最常进行的一些反应。然而，由于与沉淀的碱·HX盐有关的固体处理问题，当以连续流操作时，需要化学计量的碱来清除酸副产物带来了巨大的挑战。我们提出了一种通用而简单的策略，通过使用除酸有机碱来克服这些固体处理问题，这些酸在质子化时会生成低至中等熔点的离子液体。展示了这些碱在最常用的替代品上的应用，使反应能够在流动条件下进行，而无需其他设备，特定的溶剂或稀的反应条件来防止堵塞。
• Preparation of Tertiary Amides from Carbamoyl Chlorides and Organocuprates
  作者：Laurent Lemoucheux、Thomas Seitz、Jacques Rouden、Marie-Claire Lasne

  DOI：10.1021/ol0487130

  日期：2004.10.1

  [reaction: see text] Reaction of carbamoyl chlorides with cyano-Gilman cuprates affords tertiary amides in good to excellent yields. The reaction is general due to the possibility of using reagents made either from organolithium or from Grignard compounds. The characterization of the main side products allowed for the suggestion of a possible mechanism.

  [反应：见正文]氨基甲酰氯与氰基-吉尔曼铜酸盐的反应可提供高至优收率的叔酰胺。由于可以使用由有机锂或格氏试剂制得的试剂，因此反应是一般的。主要副产物的表征允许提出可能的机制。
• Direct Functionalization of (Un)protected Tetrahydroisoquinoline and Isochroman under Iron and Copper Catalysis: Two Metals, Two Mechanisms
  作者：Michael Ghobrial、Michael Schnürch、Marko D. Mihovilovic

  DOI：10.1021/jo201511d

  日期：2011.11.4

  either simple copper or iron catalysts. N-protected and unprotected tetrahydroisoquinolines (THIQ) could be used as starting materials. Extension of the substrate scope of the pronucleophile from indoles to pyrroles and electron-rich arenes was realized. Additionally, methoxyphenylation is not limited to THIQ but can be carried out on isochroman as well, again employing iron and copper catalysis.

  使用简单的铜或铁催化剂开发了一种高度简便、直接的 1-(3-吲哚基)-四氢异喹啉合成方法。N-保护和未保护的四氢异喹啉(THIQ)可用作起始材料。实现了亲核试剂的底物范围从吲哚扩展到吡咯和富电子芳烃。此外，甲氧基苯基化不限于 THIQ，也可以在异色满上进行，同样采用铁和铜催化。