(S)-(1,2,3,4-tetrahydroquinolin-2-yl)-methanol | 63430-96-6

• 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)-(1,2,3,4-tetrahydroquinolin-2-yl)-methanol
• 英文别名: (S)-2-hydroxymethyl-1,2,3,4-tetrahydroquinoline；(S)-(1,2,3,4-Tetrahydroquinolin-2-yl)methanol；[(2S)-1,2,3,4-tetrahydroquinolin-2-yl]methanol
• CAS: 63430-96-6
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: QSDYZRIUFBMUGV-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (S)-(1,2,3,4-tetrahydroquinolin-2-yl)-methanol 在 咪唑 、 盐酸 、 氯化亚砜 、 碘 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 20.67h， 生成 methyl (S)-1,2,3,4-tetrahydroquinoline-2-acetate
  参考文献：
  名称：

  Tricyclic Quinoxalinediones: 5,6-Dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-diones and 6,7-Dihydro-1H,5H-pyrido[1,2,3-de]quinoxaline-2,3-diones as Potent Antagonists for the Glycine Binding Site of the NMDA Receptor

  摘要：

  A series of tricyclic quinoxalinediones, 5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-diones and 6,7-dihydro-1H,5H-pyrido[1,2,3-de]quinoxaline-2,3-diones, were synthesized and was evaluated for their affinity for the glycine binding site of the NMDA receptor using a [H-3]- 5,7-dichlorokynurenic acid binding assay. The six-membered ring-fused tricyclic quinoxalinedione 18g (K-i = 9.9 nM) displayed high affinity for the glycine site. The anilide derivative 20g (K-i = 2.6 nM) was 4-fold more potent than 18g and as potent as L-689,560, one of the most potent glycine antagonists so far prepared. Although the carboxylic acid derivative of the corresponding five-membered ring-fused tricyclic quinoxalinedione 18e (K-i = 7.3 nM) had affinity comparable to that of 18g, the anilide derivative 20e largely decreased in the affinity in contrast to 20g. Enantiomers 23g, 24g, 25g, and 26g were prepared and tested. Only the S enantiomer 25g (K-i = 0.96 nM) retained the affinity among the anilide derivatives, whereas both enantiomers 23g (K-i = 2.3 nM) and 24g (K-i = 9.6 nM) were active among the carboxylic acid derivatives. The origin of the high affinity of carboxylic acid derivatives such as 18e and 18g would be a charge-charge interaction between the anionic carboxylate residues of the compounds and the cationic proton-donor site in the receptor.

  DOI：

  10.1021/jm00049a015
• 作为产物：
  描述：

  (S)-1,2,3,4-四氢喹啉-2-羧酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 (S)-(1,2,3,4-tetrahydroquinolin-2-yl)-methanol
  参考文献：
  名称：

  Tricyclic Quinoxalinediones: 5,6-Dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-diones and 6,7-Dihydro-1H,5H-pyrido[1,2,3-de]quinoxaline-2,3-diones as Potent Antagonists for the Glycine Binding Site of the NMDA Receptor

  摘要：

  A series of tricyclic quinoxalinediones, 5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-diones and 6,7-dihydro-1H,5H-pyrido[1,2,3-de]quinoxaline-2,3-diones, were synthesized and was evaluated for their affinity for the glycine binding site of the NMDA receptor using a [H-3]- 5,7-dichlorokynurenic acid binding assay. The six-membered ring-fused tricyclic quinoxalinedione 18g (K-i = 9.9 nM) displayed high affinity for the glycine site. The anilide derivative 20g (K-i = 2.6 nM) was 4-fold more potent than 18g and as potent as L-689,560, one of the most potent glycine antagonists so far prepared. Although the carboxylic acid derivative of the corresponding five-membered ring-fused tricyclic quinoxalinedione 18e (K-i = 7.3 nM) had affinity comparable to that of 18g, the anilide derivative 20e largely decreased in the affinity in contrast to 20g. Enantiomers 23g, 24g, 25g, and 26g were prepared and tested. Only the S enantiomer 25g (K-i = 0.96 nM) retained the affinity among the anilide derivatives, whereas both enantiomers 23g (K-i = 2.3 nM) and 24g (K-i = 9.6 nM) were active among the carboxylic acid derivatives. The origin of the high affinity of carboxylic acid derivatives such as 18e and 18g would be a charge-charge interaction between the anionic carboxylate residues of the compounds and the cationic proton-donor site in the receptor.

  DOI：

  10.1021/jm00049a015

文献信息

• Substituted Sulfonamide Compounds
  申请人：Oberboersch Stefan

  公开号：US20090264400A1

  公开（公告）日：2009-10-22

  Substituted sulfonamide compounds corresponding to formula I: processes for the preparation thereof, pharmaceutical compositions containing these compounds, and the use of such substituted sulfonamide compounds in pharmaceutical compositions for the treatment and/or inhibition of pain and other conditions at least partly mediated by the bradykinin 1 receptor.

  将与式I相对应的磺胺基取代化合物：其制备方法，含有这些化合物的药物组合物，以及在药物组合物中使用这些磺胺基取代化合物治疗和/或抑制至少部分由激肽酶1受体介导的疼痛和其他病症的用途。
• A Novel Ligand for the Enantioselective Ruthenium-Catalyzed Olefin Metathesis
  作者：Axel Kannenberg、Daniel Rost、Stefan Eibauer、Sascha Tiede、Siegfried Blechert

  DOI：10.1002/anie.201007673

  日期：2011.3.28

  A bridge connects and efficiently transfers the chirality from the backbone of a N‐heterocyclic carbene (NHC) to the metal center. The result is excellent enantioselectivities in the ruthenium‐catalyzed, asymmetric ring‐opening cross‐metathesis of norbornenes with allyltrimethylsilane (see scheme).

  桥连接并有效地将手性从N杂环卡宾（NHC）的骨架传递到金属中心。结果是降冰片烯与烯丙基三甲基硅烷在钌催化的不对称开环交叉复分解中具有出色的对映选择性（参见方案）。
• Highly Enantioselective Iridium-Catalyzed Hydrogenation of Heteroaromatic Compounds, Quinolines
  作者：Wen-Bo Wang、Sheng-Mei Lu、Peng-Yu Yang、Xiu-Wen Han、Yong-Gui Zhou

  DOI：10.1021/ja0353762

  日期：2003.9.1

  The highly enantioselective hydrogenation of quinoline derivatives is developed using [Ir(COD)Cl]2/(R)-MeO-Biphep/I2 system, and this methodology has been applied to the asymmetric synthesis of three naturally occurring alkaloids angustureine, galipinine, and cuspareine. This method provided an efficient access to a variety of optically active tetrahydroquinolines with up to 96% ee.

  喹啉衍生物的高度对映选择性氢化是使用 [Ir(COD)Cl]2/(R)-MeO-Biphep/I2 系统开发的，该方法已应用于三种天然生物碱 angustureine、galipinine 和葛根素。这种方法可以有效地获得各种具有高达 96% ee 的光学活性四氢喹啉。
• Synthesis of new chiral 2-functionalized-1,2,3,4-tetrahydroquinoline derivatives via asymmetric hydrogenation of substituted quinolines
  作者：Anna M. Maj、Isabelle Suisse、Christophe Hardouin、Francine Agbossou-Niedercorn

  DOI：10.1016/j.tet.2013.07.090

  日期：2013.11

  The asymmetric hydrogenation of a series of quinolines substituted by a variety of functionalized groups linked to the C2 carbon atom is providing access to optically enriched 2-functionalized 1,2,3,4-tetrahydroquinolines in the presence of in situ generated catalysts from [Ir(cod)Cl]2, a bisphosphine, and iodine. The enantioselectivity levels were as high as 96% ee.

  一系列喹啉通过多种连接于C2碳原子官能团取代的不对称氢化提供原位获得光学富集2官能-1,2,3,4-四氢喹啉在存在从产生的[Ir催化剂（COD）CL] 2，双膦，和碘。对映选择性水平高达96％ee。
• Consecutive Intermolecular Reductive Amination/Asymmetric Hydrogenation: Facile Access to Sterically Tunable Chiral Vicinal Diamines and N‐Heterocyclic Carbenes
  作者：Ya Chen、Yixiao Pan、Yan‐Mei He、Qing‐Hua Fan

  DOI：10.1002/anie.201909919

  日期：2019.11.18

  transformed into sterically hindered chiral N-heterocyclic carbene (NHC) precursors, which are otherwise difficult to access. The usefulness of this synthetic approach was further demonstrated by the successful application of one of the chiral vicinal diamines and chiral NHC ligands in a transition-metal-catalyzed asymmetric Suzuki-Miyaura cross-coupling reaction and asymmetric ring-opening cross-metathesis

  已经开发出具有2-喹啉醛和芳族胺的高度对映选择性的铱或钌催化的分子间还原胺化/不对称氢化继电器。以高收率（高达95％）和出色的对映选择性（高达> 99％ee）获得了范围广泛的空间可调性手性N，N'-二芳基邻位二胺。所得的手性二胺很容易转化为空间受阻的手性N-杂环卡宾（NHC）前体，否则很难获得。通过将手性邻位二胺和手性NHC配体之一分别成功应用在过渡金属催化的不对称Suzuki-Miyaura交叉偶联反应和不对称开环交叉复分解中，进一步证明了这种合成方法的有效性。