1,2,3,4-tetrahydropyrido[2,1-a]isoindol-6(10bH)-one | 80999-05-9

• 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-tetrahydropyrido[2,1-a]isoindol-6(10bH)-one
• 英文别名: 1,3,4,10b-tetrahydropyrido[2,1-a]isoindol-6(2H)-one；1,2,3,4,6,10b-hexahydropyrido[2,1-a]isoindol-6-one；2,3,4,10b-tetrahydro-1H-pyrido[1,2-b]isoindol-6-one
• CAS: 80999-05-9
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: LAUGPFSAEWMVNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  1,2,3,4-tetrahydropyrido[2,1-a]isoindol-6(10bH)-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以66%的产率得到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 Grubbs catalyst first generation 、 5%-palladium/activated carbon 、 [Cp*Ir(SnCl₃)2{SnCl₂(H₂O)2}]*3H₂O 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 1,2,3,4-tetrahydropyrido[2,1-a]isoindol-6(10bH)-one
  参考文献：
  名称：

  A Multimetallic Piano-Stool Ir–Sn₃ Catalyst for Nucleophilic Substitution Reaction of γ-Hydroxy Lactams through N-Acyliminium Ions

  摘要：

  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.

  DOI：

  10.1021/jo202359e

文献信息

• 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。
• A removable functional group in a photochemical macrocyclic synthesis
  作者：Masao Wada、Hideo Nakai、Yasuhiko Sato、Yasumaru Hatanaka、Yuichi Kanaoka

  DOI：10.1016/s0040-4020(01)91979-9

  日期：——

  Based on a regioselective remote photocyclization of a pair system consisting of a phthalimide group and a dithiolanyl group, a variety of aza-cyclic compounds with methylene, ester, or amide groups in their frameworks were synthesized. The dithiolanyl group provides a removable donor, which effects a needed reaction followed by removal to give a new carbon skeleton leaving little trace of the precursor

  基于由邻苯二甲酰亚胺基和二硫杂环戊烷基组成的对系统的区域选择性远程光环化，合成了在其骨架中具有亚甲基，酯或酰胺基的各种氮杂环化合物。二硫杂环戊烷基提供了可去除的供体，其影响了所需的反应，随后被去除以提供新的碳骨架，几乎没有痕量的前体形式。
• Activating Imides with Triflic Acid: A General Intramolecular Aldol Condensation Strategy Toward Indolizidine, Quinolizidine, and Valmerin Alkaloids
  作者：Yovanny Quevedo-Acosta、Igor D. Jurberg、Diego Gamba-Sánchez

  DOI：10.1021/acs.orglett.9b04199

  日期：2020.1.3

  A simple, inexpensive, step economic, and highly modular synthetic strategy to access izidine alkaloids is described. The key step is a TfOH-promoted intramolecular aldol condensation between enol and cyclic imide moieties. This cyclization strategy can be employed within an aza-Robinson annulation framework and represents a general tool to build fused bicyclic amines. To illustrate the power of this

  描述了一种简单、廉价、步骤经济且高度模块化的合成策略来获取齐嗪生物碱。关键步骤是 TfOH 促进烯醇和环状酰亚胺部分之间的分子内羟醛缩合。这种环化策略可以在氮杂罗宾逊环化框架内采用，并且代表了构建稠合双环胺的通用工具。为了说明该方法的功效，我们描述了 (±)-coniceine、(±)-quinolizidine、(±)-tashiromine、(±)-epilupinine 和 (±)-valmerins 核心的制备。
• 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.
• Wada, Masao; Nakai, Hideo; Sato, Yasuhiko, Chemical and pharmaceutical bulletin, 1982, vol. 30, p. 3414 - 3417
  作者：Wada, Masao、Nakai, Hideo、Sato, Yasuhiko、Kanaoka, Yuichi

  DOI：——

  日期：——