3-(环丙基氨基)-5,5-二甲基环己-2-烯-1-酮 | 848233-25-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(环丙基氨基)-5,5-二甲基环己-2-烯-1-酮
• 英文名称: 3-(cyclopropylamino)-5,5-dimethylcyclohex-2-enone
• 英文别名: 2-Cyclohexen-1-one, 3-(cyclopropylamino)-5,5-dimethyl-；3-(cyclopropylamino)-5,5-dimethylcyclohex-2-en-1-one
• CAS: 848233-25-0
• 化学式: C₁₁H₁₇NO
• mdl: MFCD07330022
• 分子量: 179.262
• InChiKey: WQTSNORXONFLEV-UHFFFAOYSA-N

物化性质

• 沸点：
  282.5±30.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.727
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(环丙基氨基)-5,5-二甲基环己-2-烯-1-酮 、 1-(4-chloro-phenyl)-2,2-dihydroxy-ethanone 反应 0.3h， 生成 2-(4-bromophenyl)-1-cyclopropyl-6,7-dihydro-6,6-dimethyl-7-(phenylthio)-1H-indol-4(5H)-one
  参考文献：
  名称：

  布朗斯台德酸促进的烯胺酮发散反应：具有不同取代模式的熔融吡咯的高效合成

  摘要：

  建立了布朗斯台德酸促进的发散方法，用于合成具有不同取代模式的多官能化稠合吡咯（44个实例）。通过改变充电顺序来控制发散途径，以选择性地产生一系列新的稠合吡咯。两步一锅反应可直接形成C（sp 3）S键。

  DOI：

  10.1002/adsc.201200280

文献信息

• Single step incorporation of isatin to enaminone: a recyclable catalyst towards assembly of diverse four ring fused pyrrolo[2,3,4-kl]acridin-1-ones
  作者：Chunmei Li、Furen Zhang

  DOI：10.1039/c6ra18048e

  日期：——

  Single step synthesis of four ring fused pyrrolo[2,3,4-kl]acridin-1-ones using recoverable sulfonated carbonaceous material as heterogeneous catalyst.

  使用可回收的磺化碳质材料作为非均相催化剂，实现了一步合成四环融合的吡咯并[2,3,4-kl]吖啶酮。
• 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。
• Regiospecific synthesis of 1,5,6,7-tetrahydro-4H-indol-4-ones via dehydroxylated [3+2] cyclization of β-hydroxy ketones with cyclic enaminones
  作者：Xin-Chan Lan、Ting-Ting Chen、Yan Zhao、Yu Wu、Jing Wang、Shu-Jiang Tu、Bo Jiang、Wen-Juan Hao

  DOI：10.1016/j.tetlet.2017.03.009

  日期：2017.4

  cyclization strategy has been established, allowing a flexible, practical and regiospecific approach to 23 examples of 1,5,6,7-tetrahydro-4H-indol-4-ones from low-cost and readily accessible β-hydroxy ketones and cyclic enaminones. Notably features of this work include broad functional group compatibility, mild reaction conditions and good reaction yields.

  已经建立了一种新的p -TsOH促进的脱羟基[3 + 2]环化策略，该方法可以灵活，实用且对区域特定的方法来处理23个来自1,5,6,7-tetrahydro-4 H -indol -4- one的实例低成本且易于获得的β-羟基酮和环状烯胺酮。这项工作的显着特点包括广泛的官能团相容性，温和的反应条件和良好的反应收率。
• Efficient and direct synthesis of poly-substituted indeno[1,2-b]quinolines assisted by p-toluene sulfonic acid using high-temperature water and microwave heating via one-pot, three-component reaction
  作者：Shu-Jiang Tu、Bo Jiang、Jun-Yong Zhang、Run-Hong Jia、Yan Zhang、Chang-Sheng Yao

  DOI：10.1039/b611462h

  日期：——

  Reactions of aldehydes, 1,3-indanedione and enaminones were successfully carried out using p-toluene sulfonic acid (p-TsOH) as a catalyst and high-temperature water as a solvent under microwave irradiation. This method provided several advantages such as rapid reaction times, high yields, and a simple workup procedure. In addition, a possible mechanism to account for the reaction was proposed.

  以对甲苯磺酸（p-TsOH）为催化剂，以高温水为溶剂，在微波辐照下成功地进行了醛、1,3-茚二酮和烯酮的反应。该方法具有反应时间短、产率高、操作步骤简单等优点。此外，还提出了一种可能的反应机理。
• 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。