1,2,3,4-tetrahydro-6-methoxy-2-phenylquinoline | 199186-66-8

• 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: 1,2,3,4-tetrahydro-6-methoxy-2-phenylquinoline
• 英文别名: 6-Methoxy-2-phenyl-1,2,3,4-tetrahydroquinoline
• CAS: 199186-66-8；199186-67-9；337960-01-7
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: IJRFTWYVZWDLFP-UHFFFAOYSA-N

物化性质

• 沸点：
  413.5±45.0 °C(Predicted)
• 密度：
  1.085±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-6-methoxy-2-phenylquinoline 在 三溴化硼 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (6-Hydroxy-2-phenyl-3,4-dihydro-2H-quinolin-1-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone
  参考文献：
  名称：

  Tetrahydroquinoline-Based selective estrogen receptor modulators (SERMs)

  摘要：

  A new series of estrogen receptor ligands based on a 6-hydroxy-tetrahydroquinoline scaffold is described, in addition to their binding affinity and functional activity in MCF-7 cells. Several 1,2-disubstituted tetrahydroquinolines bearing a basic side chain were shown to be high affinity ligands and antagonists in the MCF-7 proliferation assay. Compounds lacking the basic side chain were agonists in the MCF-7 assay. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00306-8
• 作为产物：
  描述：

  6-甲氧基-2-苯基喹啉 在 乙醇 、 sodium 作用下， 生成 1,2,3,4-tetrahydro-6-methoxy-2-phenylquinoline
  参考文献：
  名称：

  Tetrahydroquinoline-Based selective estrogen receptor modulators (SERMs)

  摘要：

  A new series of estrogen receptor ligands based on a 6-hydroxy-tetrahydroquinoline scaffold is described, in addition to their binding affinity and functional activity in MCF-7 cells. Several 1,2-disubstituted tetrahydroquinolines bearing a basic side chain were shown to be high affinity ligands and antagonists in the MCF-7 proliferation assay. Compounds lacking the basic side chain were agonists in the MCF-7 assay. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00306-8

文献信息

• Efficient Entry into 2-Substituted Tetrahydroquinoline Systems through Alkylative Ring Expansion: Stereoselective Formal Synthesis of (±)-Martinellic Acid
  作者：Masafumi Ueda、Sayuri Kawai、Masataka Hayashi、Takeaki Naito、Okiko Miyata

  DOI：10.1021/jo902540x

  日期：2010.2.5

  new efficient synthesis of 2-substituted tetrahydroquinolines has been achieved by the domino reaction of N-indanyl(methoxy)amines, which consists of three types of reactions: elimination of an alcohol, the rearrangement of an aryl group, and the addition of an organolithium or magnesium reagent. The synthetic utility of this approach is demonstrated by the stereoselective formal synthesis of (±)- martinellic

  通过N-茚满基（甲氧基）胺的多米诺反应已实现了一种新的有效的2-取代四氢喹啉合成方法，该反应包括三种类型的反应：消除醇，重整芳基和添加芳基。有机锂或镁试剂。这种方法的合成效用通过（±）-丁二酸的立体选择性形式合成得到证明。
• 2-substituted 1,2,3,4-tetrahydroquinolines and derivatives thereof, compositions and methods
  申请人：——

  公开号：US20040215018A1

  公开（公告）日：2004-10-28

  The current invention provides novel 2-substituted 1,2,3,4-tetrahydroquinolin-6-ols and derivatives thereof of the formula (I) (A); pharmaceutical compositions thereof, optionally in combination with estrogen or progestin; methods for inhibiting a disease associated with estrogen deprivation; and methods for inhibiting a disease associated with an aberrant physiological response to endogenous estrogen. 1

  当前发明提供了新型的2-取代的1,2,3,4-四氢喹啉-6-醇及其衍生物，其化学式为(I) (A)；其中包括与雌激素或孕激素可选地结合的制药组合物；用于抑制与雌激素缺乏有关的疾病的方法；以及用于抑制与内源性雌激素异常生理反应有关的疾病的方法。
• Tetrahydroquinolin derivatives for the inhibition of diseases associated with estrogen deprivation or with an aberrant physiological response to endogenous estrogen
  申请人：——

  公开号：US20040132770A1

  公开（公告）日：2004-07-08

  The current invention provides methods for inhibiting a disease associated with estrogen deprivation and for inhibiting disease associated with an aberrant physiological response to endogenous estrogen comprising administering 2-substituted 1,2,3,4-tetrahydroquinolin-6-ols and derivatives thereof.

  本发明提供了一种抑制与雌激素缺乏相关疾病和抑制与内源性雌激素异常生理反应相关疾病的方法，包括给予2-取代的1,2,3,4-四氢喹啉-6-醇及其衍生物。
• Light-driven redox deracemization of indolines and tetrahydroquinolines using a photocatalyst coupled with chiral phosphoric acid
  作者：Qipeng Chen、Yuanli Zhu、Xujing Shi、Renfu Huang、Chuang Jiang、Kun Zhang、Guohua Liu

  DOI：10.1039/d2sc06340a

  日期：——

  The integration of oxidation and enantioselective reduction enables a redox deracemization to directly access enantioenriched products from their corresponding racemates. However, the solution of the kinetically microscopic reversibility of substrates used in this oxidation/reduction unidirectional event is a great challenge. To address this issue, we have developed a light-driven strategy to enable

  氧化和对映选择性还原的结合使氧化还原去外消旋化能够直接从相应的外消旋物中获得对映体富集的产物。然而，解决这种氧化/还原单向事件中使用的底物的动力学微观可逆性是一个巨大的挑战。为了解决这个问题，我们开发了一种光驱动策略，以实现环胺的有效氧化还原去外消旋化。该方法将光催化剂和手性磷酸结合在甲苯/水性环糊精乳液双相共溶剂系统中，以驱动级联失衡。系统优化实现了可行的氧化/还原级联序列，机械研究证明了单向过程。这种单操作级联路由，
• Hydrogenation of ortho-nitrochalcones over Pd/C as a simple access to 2-substituted 1,2,3,4-tetrahydroquinolines
  作者：Angela Patti、Sonia Pedotti

  DOI：10.1016/j.tet.2010.05.090

  日期：2010.7

  The preparation of some 2-substituted-1,2,3,4-tetrahydroquinoline has been achieved by the one-pot reductive intramolecular cyclization of ortho-nitrochalcones with gaseous hydrogen in the presence of a Pd/C catalyst and the best selectivity was observed using CH2Cl2 as solvent. The method is operationally simple and versatile since ortho-nitrocalchones are easily accessible by Claisen-Schmidt condensation of 2-nitrobenzaldehydes and enolizable ketones. Selected examples on structurally different substrates have been considered and a novel tetrahydroquinoline and a benzo[h]tetrahydroquinoline were prepared and characterised. (C) 2010 Elsevier Ltd. All rights reserved.