1,4,6,10b-tetrahydropyrido[2,1-a]isoindol-6-one | 1016636-47-7

• 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: 1,4,6,10b-tetrahydropyrido[2,1-a]isoindol-6-one
• 英文别名: 1,10b-dihydro-4H-pyrido[2,1-a]isoindol-6-one；1,10b-dihydropyrido[2,1-a]isoindol-6(4H)-one；4,10b-dihydro-1H-pyrido[1,2-b]isoindol-6-one
• CAS: 1016636-47-7
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: USOWQIDSFYTDQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  1,4,6,10b-tetrahydropyrido[2,1-a]isoindol-6-one 在 lithium aluminium tetrahydride 、 甲酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 18.0h， 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
• 作为产物：
  描述：

  2-allyl-3-hydroxyisoindolin-1-one 在 吡啶 、 Grubbs catalyst first generation 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 1,4,6,10b-tetrahydropyrido[2,1-a]isoindol-6-one
  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

• Contrasting Responses of Pyrido[2,1-<i>a</i>]isoindol-6-ones and Their Sultam Counterparts to Photochemical Activation
  作者：Leo A. Paquette、Robert D. Dura、Isabelle Modolo

  DOI：10.1021/jo802476c

  日期：2009.3.6

  sultam counterparts. The synthetic routing takes advantage of the ready availability of N-allylphthalimide and N-allylsaccharin and proceeds via the proper incorporation of small side chains into the heterocyclic ring. Positionally selective introduction of the conjugated diene functionality was realized efficiently. Detailed study of the excited-state chemistry of 7 and 8 showed both lactams to be

  基于闭环置换的策略允许访问未报告的一对吡啶并异吲哚酮及其先前未知的sultam对应物。合成路线利用了N-烯丙基邻苯二甲酰亚胺和N-烯丙基糖精的现成优势，并且通过将小侧链适当地掺入杂环中而进行。有效地实现了共轭二烯官能团的位置选择性引入。对7和8的激发态化学的详细研究表明，两种内酰胺均在丙酮敏感的条件下经历[4 + 2]二聚化。涉及不同的区域选择性，响应为8比7所显示的效率高得多。在任何条件下都无法从9和10的光解产物中分离出二聚体。当后者的苏丹阿酰胺进行广泛的聚合反应时，9通过在350 nm处的直接照射分别通过涉及S-N键和杂环裂解的[1,3]-σ转变为46和47。
• 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。
• Catalytic Cyclization of Alkenyl<i>N</i>,<i>O</i>-Acetals by Fe(OTf)₃
  作者：Kimihiro Komeyama、Ryoichi Igawa、Takayuki Morimoto、Ken Takaki

  DOI：10.1246/cl.2009.724

  日期：2009.7.5

  Fe(OTf)3, was found to be a good catalyst for the cyclization of alkenyl N,O-acetals to give various nitrogen-containing heterocycles in high yields.

  Fe(OTf)3 被发现是烯基 N,O-缩醛环化的良好催化剂，可以高产率得到各种含氮杂环。
• A Multimetallic Piano-Stool Ir–Sn₃ Catalyst for Nucleophilic Substitution Reaction of γ-Hydroxy Lactams through <i>N</i>-Acyliminium Ions
  作者：Arnab Kumar Maity、Sujit Roy

  DOI：10.1021/jo202359e

  日期：2012.3.16

  A multimetallic piano-stool complex [Cp*Ir-(SnCl3)(2)SnCl2(H2O)(2)}] (1) having Ir-Sn-3 motif has been synthesized from [Cp*IrCl2](2) and SnCl2. The multimetallic complex catalytically promotes the nucleophilic substitution reaction (here after alpha-amidoalkylation reaction) of gamma-hydroxylactams generated from phthalimidals to obtain decorated isoindolinones in excellent yields. Succinamidals, however, lead to the substituted pyrrolidinones (thermodynamic control product) via S(N)1-type path as well as eliminated pyrrolinones (kinetic control product) via an E1-type path, depending on the reaction parameters. A straightforward application of this methodology is to synthesize benzo-fused indolizidine alkaloid mimics.
• Dura, Robert D.; Modolo, Isabelle; Paquette, Leo A., Heterocycles, 2007, vol. 74, # C, p. 145 - 148
  作者：Dura, Robert D.、Modolo, Isabelle、Paquette, Leo A.

  DOI：——

  日期：——