3-[(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)amino]propanoic acid | 102688-94-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-[(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)amino]propanoic acid
• 英文别名: 3-[(5,5-dimethyl-3-oxocyclohexen-1-yl)amino]propanoic acid
• CAS: 102688-94-8
• 化学式: C₁₁H₁₇NO₃
• mdl: MFCD02239751
• 分子量: 211.261
• InChiKey: UOUJSQIEWUCXDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.636
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)amino]propanoic acid 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 甲醇 、 水 为溶剂， 以65%的产率得到3-[(2-bromo-5,5-dimethyl-3-oxocyclohexen-1-yl)amino]propanoic acid
  参考文献：
  名称：

  Amino-derivatives of 4-methoxy-7,8-dihydro-1,3-diazaphenothiazine and their neurotropic activity

  摘要：

  DOI：

  10.1007/bf00766681
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 β-丙氨酸 以 苯 为溶剂， 以80%的产率得到3-[(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)amino]propanoic acid
  参考文献：
  名称：

  Amino-derivatives of 4-methoxy-7,8-dihydro-1,3-diazaphenothiazine and their neurotropic activity

  摘要：

  DOI：

  10.1007/bf00766681

文献信息

• Allylic Amination and <i>N</i>-Arylation-Based Domino Reactions Providing Rapid Three-Component Strategies to Fused Pyrroles with Different Substituted Patterns
  作者：Bo Jiang、Ying Li、Man-Su Tu、Shu-Liang Wang、Shu-Jiang Tu、Guigen Li

  DOI：10.1021/jo301323r

  日期：2012.9.7

  New three-component domino reaction providing divergent approaches to multifunctionalized fused pyrroles with different substituted patterns have been established (40 examples). The direct C(sp3)–N bond formation was achieved through intermolecular allylic amination in a one-pot operation, and N-arylation of amines was realized by varying N-amino acid enaminones. The reaction is easy to perform simply

  已经建立了新的三组分多米诺骨牌反应，为具有不同取代模式的多功能化稠合吡咯提供了不同的方法（40 个例子）。通过一锅操作的分子间烯丙胺化实现了C(sp 3 )-N键的直接形成，并通过改变N-氨基酸烯胺实现了胺的N-芳基化。该反应很容易进行，只需在微波加热下将三种常见反应物在乙酸中混合即可。反应进行速度快，可在 30 分钟内完成，这使得后处理方便，可以获得良好的化学产率。
• A domino synthetic strategy leading to two-carbon-tethered fused acridine/indole pairs and fused acridine derivatives
  作者：Bo Jiang、Xue Wang、Meng-Yuan Li、Qiong Wu、Qin Ye、Hai-Wei Xu、Shu-Jiang Tu

  DOI：10.1039/c2ob26315g

  日期：——

  pairs were synthesized via Brønsted acid-promoted domino reactions between indoline-2,3-dione and C2-tethered indol-3-yl enaminones. The reactions were further expanded to prepare C-tethered fused acridine/pyridine pairs, N-substituted amino acids, N-cyclopropyl and N-aryl substituted fused acridine derivatives, as well as bis-furan-3-yl-substituted indoles. During these reaction processes, the domino

  一系列新型的多官能化的两碳束缚电熔 cr啶/吲哚对通过布朗斯台德酸促进的多米诺骨牌反应合成吲哚啉-2,3-二酮和C 2系联的吲哚-3-基烯胺酮。反应进一步扩大以制备C系链的稠合cr啶/吡啶对，N-取代的氨基酸，N-环丙基和N-芳基取代的稠合a啶衍生物以及双呋喃-3-基取代的吲哚。在这些反应过程中，通过一锅操作很容易实现了稠合的cr啶骨架的多米诺结构以及同时形成的两个新环。该过程是容易的，避免了费时和昂贵的合成，繁琐的后处理和前体纯化。
• One-Pot Three-Component Synthesis of Polysubstituted Tetrahydroindoles
  作者：Nataliia V. Chechina、Nadezhda N. Kolos、Irina V. Omelchenko

  DOI：10.1007/s10593-019-02600-8

  日期：2019.12

  A series of novel fused pyrrole derivatives was synthesized by one-pot three-component reaction of β-enaminoketones, derived from cyclohexane-1,3-dione or dimedone, arylglyoxal hydrates, and 1,3-dimethylbarbituric acid in EtOH.

  通过一锅三组分反应制取一系列新颖的稠合吡咯衍生物，该衍生物由环己烷-1,3-二酮或二酮，芳基乙二醛水合物和1,3-二甲基巴比妥酸在EtOH中衍生而来。
• Synthesis of 3-substituted tetrahydroindol-4-one
  作者：Nadiia N. Kolos、Kateryna I. Marchenko、Nataliia V. Chechina、Alexander V. Buravov、Irina V. Omelchenko

  DOI：10.1007/s10593-021-03041-y

  日期：2021.12

  A series of functionalized 4,5,6,7-tetrahydroindol-4-one derivatives containing a residue derived from β-dicarbonyl compound at position 3 were prepared by a reaction of cyclic enaminones, arylglyoxal hydrates, and β-dicarbonyl compounds. Modification of acetylacetone residue at position 3 of tetrahydroindoles was accomplished by condensation with 1,2- and 1,4-bisnucleophiles.

  通过环状烯胺酮、芳基乙二醛水合物和β-二羰基化合物的反应制备了一系列功能化的4,5,6,7-四氢吲哚-4-酮衍生物，该衍生物在3位含有衍生自β-二羰基化合物的残基。通过与 1,2- 和 1,4- 双亲核试剂缩合完成四氢吲哚 3 位乙酰丙酮残基的修饰。
• One-Pot Synthesis of N-Substituted Azapodophyllotoxin Derivatives under Microwave Irradiation
  作者：Shujiang Tu、Shunjun Ji、Yan Zhang、Bo Jiang、Runhong Jia、Junyong Zhang、Jinpeng Zhang

  DOI：10.1055/s-2006-950297

  日期：2006.11

  A series of new, N-substituted azapodophyllotoxin derivatives were synthesized via a three-component reaction of an aldehyde, an enaminone and tetronic acid in glacial acetic acid, under microwave irradiation, without a catalyst. This new protocol has the advantages of shorter time, higher yields, lower cost and broader substrate scope, as well as easier operation.

  通过醛、烯胺酮和特罗尼酸在冰醋酸中，在微波辐射下，无催化剂的三组分反应，合成了一系列新型 N 取代的氮杂鬼臼毒素衍生物。这种新协议具有时间更短、产量更高、成本更低、基材范围更广、操作更简单等优点。