1,2,3,4,6,10b-hexahydropyrido[2,1-a]isoindole | 14174-89-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 1,2,3,4,6,10b-hexahydropyrido[2,1-a]isoindole
• CAS: 14174-89-1
• 化学式: C₁₂H₁₅N
• 分子量: 173.258
• InChiKey: XTHNIQHRXBDUJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-allyl-3-hydroxyisoindolin-1-one 在 吡啶 、 Grubbs catalyst first generation 、 lithium aluminium tetrahydride 、 甲酸 、 三氟甲磺酸三甲基硅酯 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 54.0h， 生成 1,2,3,4,6,10b-hexahydropyrido[2,1-a]isoindole
  参考文献：
  名称：

  Synthesis of 3-substituted N-allylisoindolinone derivatives by the acetate method

  摘要：

  A series of N-allylisoindolinone derivatives were prepared by a novel sequential reaction of 2-allyl-3-oxoisoindolin-1-yl acetate with C-nucleophiles in the presence of trimethylsilyl trifluoromethanesulfonate. The nucleophiles included arenes, alkenes, and active methylene to give 3-substituted N-allylisoindolinone products. This method was applied to synthesize cyclohexane-fused indolizidine alkaloid mimics using Grubbs' catalyst..

  DOI：

  10.1007/s00706-013-1127-z

文献信息

• Synthesis of Polycyclic Isoindolines via α-C–H/N–H Annulation of Alicyclic Amines
  作者：Anirudra Paul、Camille Vasseur、Scott D. Daniel、Daniel Seidel

  DOI：10.1021/acs.orglett.2c00018

  日期：2022.2.11

  situ from their corresponding alicyclic amines via oxidation of their lithium amides with simple ketone oxidants, engage aryllithium compounds containing a leaving group on an ortho-methylene functionality to provide polycyclic isoindolines in a single operation. The scope of this transformation includes pyrrolidine, piperidine, azepane, azocane, and piperazines.

  相对不稳定的环状亚胺是通过用简单的酮氧化剂氧化其氨基锂而由相应的脂环胺原位生成的，与邻亚甲基官能团上含有离去基团的芳基锂化合物接合，在单一操作中提供多环异吲哚啉。该转化的范围包括吡咯烷、哌啶、氮杂环庚烷、氮佐烷和哌嗪。
• Short diastereoselective synthesis of cis- and trans-hexahydropyrido[2,1-a]isoindole derivatives
  作者：Ala’Eddin Alsarabi、Jean-Louis Canet、Yves Troin

  DOI：10.1016/j.tetlet.2004.10.045

  日期：2004.11

  A new and highly stereoselective access to 4,10b-trans or 4,10b-cis hexahydropyrido[2,1-a]isoindole derivatives is reported, both requiring an intramolecular Mannich-type reaction as key step. The cis diastereoisomer is obtained in three steps from a 2-alkyl benzaldehyde through the stereoselective formation of a 2,6-cis-disubstituted piperidine, while the trans stereomer is efficiently obtained, in

  报道了对4,10b-反式或4,10b-顺式六氢吡啶并[ 2,1 - a ]异吲哚衍生物的新型且高度立体选择性的进入，两者均需要分子内曼尼希型反应作为关键步骤。的顺式非对映体在三个步骤中通过立体选择性形成的2,6-获得从2-烷基苯甲醛顺式二取代的哌啶，而反是有效地获得stereomer，在一个单一的步骤中，如果一个2-甲酰基苯甲酸是参与曼尼希环化过程。
• Synthesis of diversely functionalized pyrrolizidines and indolizidines using olefin ring-closing metathesis
  作者：Raja Ben-Othman、Mohamed Othman、Kabula Ciamala、Michael Knorr、Carsten Strohmann、Bernard Decroix

  DOI：10.1016/j.tet.2009.04.039

  日期：2009.6

  synthesized via ene–ene metathesis using the first and second-generation Grubbs catalyst. The ene–ene metathesis proceeded smoothly in refluxing CH2Cl2 with 3.0 mol % of G1, giving good yields (78–86%) of the benzoindolizidine products 12a,b. The benzopyrrolizidine 6 was prepared after optimization in 64% yield by using 5.0+5.0 mol % of G2. The resulting olefin moiety of the indolizidine framework is a suitable

  使用第一代和第二代Grubbs催化剂，通过烯-烯复分解反应，合成了具有苯并吲哚并咪唑和苯并吡咯并咪唑环系统的各种氮稠合三环化合物。烯-烯的复分解反应在CH 2 Cl 2与3.0 mol％G 1的回流下顺利进行，苯并吲哚并咪唑产物12a，b的收率良好（78-86％）。优化后，使用5.0 + 5.0 mol％的G 2以64％的收率制备了苯并吡咯烷嗪6。吲哚并立定骨架的所得烯烃部分是通过Sharpless方法的用于多羟基结构的合适的前体。通过1 H NMR光谱和单晶X射线分析确定多羟基化加合物的结构。
• Synthesis of 3-substituted N-allylisoindolinone derivatives by the acetate method
  作者：Ibrahim A. I. Ali

  DOI：10.1007/s00706-013-1127-z

  日期：2014.5

  A series of N-allylisoindolinone derivatives were prepared by a novel sequential reaction of 2-allyl-3-oxoisoindolin-1-yl acetate with C-nucleophiles in the presence of trimethylsilyl trifluoromethanesulfonate. The nucleophiles included arenes, alkenes, and active methylene to give 3-substituted N-allylisoindolinone products. This method was applied to synthesize cyclohexane-fused indolizidine alkaloid mimics using Grubbs' catalyst..