(S)-6-phenyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]quinoline | 1159987-38-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (S)-6-phenyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]quinoline
• 英文别名: (6S)-6-phenyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]quinoline
• CAS: 1159987-38-8
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: XFRQGYWIGUZMHR-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-(3-phenylprop-2-yn-1-yl)benzo[d][1,3]dioxol-5-amine 在 (11bS)-4-羟基-2,6-二[2,4,6-三(异丙基)苯基]-二萘并[2,1-d:1',2'-f][1,3,2]二氧杂磷杂卓4-氧化物 、 二氢吡啶 、 [IMesAuMe] 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以70%的产率得到(S)-6-phenyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]quinoline
  参考文献：
  名称：

  Chiral Gold Phosphate Catalyzed Tandem Hydroamination/Asymmetric Transfer Hydrogenation Enables Access to Chiral Tetrahydroquinolines

  摘要：

  A highly efficient chiral gold phosphate-catalyzed tandem hydroamination/asymmetric transfer hydrogenation reaction is described. A series of chiral tetrahydroquinolines were obtained in excellent yields and enantioselectivities. In this reaction, the gold catalyst enables both the hydroamination step as a pi-Lewis acid and the asymmetric hydrogen-transfer process as an effective chiral Lewis acid.

  DOI：

  10.1021/acs.joc.5b00153

文献信息

• Shedding light on Brønsted acid catalysis – a photocyclization–reduction reaction for the asymmetric synthesis of tetrahydroquinolines from aminochalcones in batch and flow
  作者：Hsuan-Hung Liao、Chien-Chi Hsiao、Erli Sugiono、Magnus Rueping

  DOI：10.1039/c3cc43996h

  日期：——

  A new asymmetric photocyclization–reduction cascade employing readily available aminochalcones has been developed. The reaction sequence has been achieved by unifying photochemistry and asymmetric Brønsted acid catalysis and involves photocyclization followed by Brønsted acid catalyzed enantioselective hydrogenation in batch and flow.

  已经开发了一种新的不对称光环化-还原级联反应，采用了易于获取的氨基查尔酮。该反应序列通过结合光化学和不对称布朗斯特酸催化实现，涉及光环化，随后在批量和连续流动条件下进行布朗斯特酸催化的对映选择性氢化反应。