1-(2-indol-3-yl-ethyl)-1,4-dihydro-pyridine-3-carboxylic acid methyl ester | 63195-42-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(2-indol-3-yl-ethyl)-1,4-dihydro-pyridine-3-carboxylic acid methyl ester
• 英文别名: methyl 1-[2-(1H-indol-3-yl)ethyl]-4H-pyridine-3-carboxylate
• CAS: 63195-42-6
• 化学式: C₁₇H₁₈N₂O₂
• 分子量: 282.342
• InChiKey: MIUXCYYUFDYERL-UHFFFAOYSA-N

物化性质

• 沸点：
  485.7±45.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-indol-3-yl-ethyl)-1,4-dihydro-pyridine-3-carboxylic acid methyl ester 在 N-碘代丁二酰亚胺 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Iodocyclization of 1,4-dihydropyridines

  摘要：

  Iodine (or related species) addition to 1,4-dihydropyridinls, with properly attached substituents at the nitrogen atom, leads to the corresponding 3-iodotetrahydlopyridinium ions, which undergo an internal nucleophilic attack to furnish regio- and stereoselectively iodobi(poly)heterocyclic ring systems in good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00912-5
• 作为产物：
  描述：

  3-(2-溴乙基)吲哚 在 sodium dithionite 、 碳酸氢钠 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 22.0h， 生成 1-(2-indol-3-yl-ethyl)-1,4-dihydro-pyridine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  手性四氢-β-咔啉的构建：吲哚基二氢吡啶的不对称Pictet-Spengler反应

  摘要：

  通过使用手性磷酸催化吲哚基二氢吡啶的Pictet-Spengler反应，开发了对映体富集的四氢-β-咔啉的高效合成方法。反应在温和的反应条件下进行，以良好的产率（高达96％）和高的对映选择性（高达99％ee）提供所需的手性四氢-β-咔啉。用这种方法，可以高效地完成橘皮苷的正式合成和十氢萘烷的全部合成。

  DOI：

  10.1002/anie.201703178

文献信息

• 1,4-Dihydropyridine equivalents: a novel approach to 2,6-dicyanopiperidine derivatives
  作者：Tiina Putkonen、Emmi Valkonen、Arto Tolvanen、Reija Jokela

  DOI：10.1016/s0040-4020(02)00896-7

  日期：2002.9

  For the first time, it has been shown that 2,6-dicyanopiperidines are formed in the Fry reaction via 1,4-dihydropyridine intermediates. A new synthetic approach for building 2,6-dicyanopiperidine derivatives by an extension of the sodium dithionite reduction of pyridinium salts is described. The stereochemistry of 2,6-dicyanopiperidine derivatives formed is discussed.

  首次表明，在Fry反应中通过1,4-二氢吡啶中间体形成了2,6-二氰基哌啶。描述了通过扩大连二亚硫酸钠吡啶鎓盐的还原来构建2,6-二氰基哌啶衍生物的一种新的合成方法。讨论了形成的2,6-二氰基哌啶衍生物的立体化学。
• Iodocyclisation of 1,4‐Dihydropyridines; Synthesis and Reactivity of 1‐Iodoindolo[2,3‐ <i>a</i> ]quinolizidines
  作者：Rodolfo Lavilla、Oscar Coll、Marta Nicolàs、Bilal A. Sufi、Javier Torrents、Joan Bosch

  DOI：10.1002/(sici)1099-0690(199911)1999:11<2997::aid-ejoc2997>3.0.co;2-#

  日期：1999.11
• Introduction of Heteroatom-Based Substituents into 1,4-Dihydropyridines by Means of a Halogen-Mediated, Oxidative Protocol: Diamination, Sulfonylation, Sulfinylation, Bis-Sulfanylation, and Halo-Phosphonylation Processes
  作者：Rodolfo Lavilla、Rakesh Kumar、Oscar Coll、Carme Masdeu、Alessandro Spada、Joan Bosch、Enric Espinosa、Elies Molins

  DOI：10.1002/(sici)1521-3765(20000515)6:10<1763::aid-chem1763>3.0.co;2-r

  日期：2000.5.15

  The natural tendency of 1,4-dihydropyridines to undergo "biomimetic" oxidation to afford pyridinium salts can be switched off and, through the use of reagents that interact electrophilically with the enamine moiety present in the heterocyclic system, it is possible to promote alternative oxidations. In this way, efficient regio- and stereocontrolled synthetic methods have been developed that lead to diversely substituted di- and tetrahydropyridines. These include iodoazidation, diamination, bis-sulfonamidation, sulfonylation, sulfinylation, thiocyanation, sulfanylation, bis-sulfanylation, and halo-phosphonylation processes.
• Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet-Spengler Reaction of Indolyl Dihydropyridines
  作者：Shou-Guo Wang、Zi-Lei Xia、Ren-Qi Xu、Xi-Jia Liu、Chao Zheng、Shu-Li You

  DOI：10.1002/anie.201703178

  日期：2017.6.19

  A highly efficient synthesis of the enantioenriched tetrahydro-β-carbolines was developed by using a chiral phosphoric acid catalyzed Pictet–Spengler reaction of indolyl dihydropyridines. The reaction proceeds under mild reaction conditions to afford the desired chiral tetrahydro-β-carbolines in good to excellent yields (up to 96 %) and high enantioselectivities (up to 99 % ee). With this method, a

  通过使用手性磷酸催化吲哚基二氢吡啶的Pictet-Spengler反应，开发了对映体富集的四氢-β-咔啉的高效合成方法。反应在温和的反应条件下进行，以良好的产率（高达96％）和高的对映选择性（高达99％ee）提供所需的手性四氢-β-咔啉。用这种方法，可以高效地完成橘皮苷的正式合成和十氢萘烷的全部合成。
• Iodocyclization of 1,4-dihydropyridines
  作者：Rodolfo Lavilla、Oscar Coll、Marta Nicolàs、Joan Bosch

  DOI：10.1016/s0040-4039(98)00912-5

  日期：1998.7

  Iodine (or related species) addition to 1,4-dihydropyridinls, with properly attached substituents at the nitrogen atom, leads to the corresponding 3-iodotetrahydlopyridinium ions, which undergo an internal nucleophilic attack to furnish regio- and stereoselectively iodobi(poly)heterocyclic ring systems in good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.