(+/-)-1,2,3,4-tetrahydro-5-methoxy-2-oxo-1-naphthaleneacetic acid methyl ester | 147439-59-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (+/-)-1,2,3,4-tetrahydro-5-methoxy-2-oxo-1-naphthaleneacetic acid methyl ester
• 英文别名: methyl 2-(5-methoxy-2-oxo-3,4-dihydro-1H-naphthalen-1-yl)acetate
• CAS: 147439-59-6
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: HAKNKIQJCQOULS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-1,2,3,4-tetrahydro-5-methoxy-2-oxo-1-naphthaleneacetic acid methyl ester 在 palladium on barium sulfate 氢氧化钾 、 氢气 、 一水合肼 作用下， 以 乙醇 、 乙二醇 、 苯 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  与二萜生物碱有关的合成中间体。

  摘要：

  DOI：

  10.1021/ja00960a036
• 作为产物：
  描述：

  5-甲氧基-2-萘满酮 、 溴乙酸乙酯 生成 (+/-)-1,2,3,4-tetrahydro-5-methoxy-2-oxo-1-naphthaleneacetic acid methyl ester
  参考文献：
  名称：

  与二萜生物碱有关的合成中间体。

  摘要：

  DOI：

  10.1021/ja00960a036

文献信息

• Centrally acting serotonergic and dopaminergic agents. 1. Synthesis and structure-activity relationships of 2,3,3a,4,5,9b-hexahydro-1H-benz[e]indole derivatives
  作者：Chiu Hong Lin、Susanne R. Haadsma-Svensson、Robert A. Lahti、Robert B. McCall、Montford F. Piercey、Peggy J. K. D. Schreur、Phillip F. Von Voigtlander、Martin W. Smith、Connie G. Chidester

  DOI：10.1021/jm00060a014

  日期：1993.4

  asymmetric synthesis using chiral (R)-alpha-methylbenzylamine. All analogs were evaluated in the in vitro 5-HT1A and D2 binding assays and selected analogs were investigated further in biochemical and behavioral tests. Analogs with 9-methoxy substitution (R1 in 3) showed mixed 5-HT1A agonist and dopamine antagonist activities whereas the corresponding 9-hydroxy analogs displayed selective 5-HT1A agonist

  描述了2,3,3a，4,5,9b-六氢-1H-苯并[e]吲哚衍生物（3）的合成和构效关系（SAR）。这些化合物是2-氨基四氢萘的构象受限的角三环类似物。由相应的2-四氢萘酮在几个步骤中完成合成。顺式类似物的对映异构体是由二对甲苯甲酰基-L-（或D）-酒石酸的非对映异构体盐的分步重结晶或使用手性（R）-α-甲基苄基胺的不对称合成获得的。在体外5-HT1A和D2结合试验中评估了所有类似物，并在生化和行为测试中进一步研究了所选类似物。具有9-甲氧基取代的类似物（R1在3中）显示出5-HT1A激动剂和多巴胺拮抗剂的混合活性，而相应的9-羟基类似物则具有选择性的5-HT1A激动剂活性。发现顺式类似物比相应的反式类似物更有效，并且在顺式系列中，（3aR）-（-）-对映异构体显示出更高的效力。用正丙基或烯丙基进行的氮取代（3中的R2）产生相似的活性，而用庞大的α-甲基苄基取代则导致活性降低。没有芳香取代基的类似物（3中的R1
• Concise Synthesis of Chiral Tricyclic Lactams by Tandem Dynamic Kinetic Asymmetric Reductive Amination/Lactamization Using Ammonium Salts
  作者：Jingxin Wang、Yongjie Shi、Fangyuan Wang、Fanping Huang、Shao‐Tao Bai、Yu Zhao、Xumu Zhang

  DOI：10.1002/anie.202303868

  日期：2023.6.19

  and economical one-pot approach to chiral fused tricyclic lactams from readily available ketoesters was developed by using cheap ammonium salts as the nitrogen source through ruthenium-catalyzed tandem dynamic kinetic asymmetric reductive amination/lactamization. This protocol provides highly efficient access to drug intermediates and organocatalysts containing chiral polycyclic N-heterocycles.

  通过使用廉价的铵盐作为氮源，通过钌催化的串联动力学不对称还原胺化/内酰胺化，开发了一种从现成的酮酯中制备手性稠合三环内酰胺的有效且经济的一锅法。该协议提供了对含有手性多环 N-杂环的药物中间体和有机催化剂的高效访问。
• cis- and trans-2,3,3a,4,5,9b-Hexahydro-1H-benz[e]indoles: synthesis and evaluation of dopamine D2 and D3 receptor binding affinity
  作者：Xiaodong Song、A.Michael Crider、Sharon F. Cruse、Debasis Ghosh、Cheryl Klein-Stevens、Li Liang、Mark A. Scheideler、Annemarie Varming、Inger Søtofte

  DOI：10.1016/s0223-5234(99)80098-1

  日期：1999.6

  cis- and trans-2,3,3a,4,5,9b-Hexahydro-1H-benz[e]indoles were synthesized as conformationally rigid analogues of 3-phenylpyrrolidine and evaluated for dopamine (DA) D-2S and D-3 receptor binding affinity. The tricyclic benz[e]indole nucleus was constructed by a previously reported reductive amination-cyclization procedure. Several unexpected side products were isolated and characterized using the general method. The trans-diastereoisomers exhibited greater affinities for the DA D-3 receptor than the corresponding cis-isomers. In both the cis- and trans- series the greatest affinity for DA D-3 receptors was shown by compounds substituted with N-n propyl or N-allyl groups. The cis-(+/-)-N-allyl derivative 21e demonstrated a D-2S /D-3 selectivity of 290. Resolution of cis-(+/-)-5 and trans-(+/-)-21c into individual enantiomers showed that in both series the more active isomer had 3aR absolute configuration. These novel Ligands may be useful tools for gaining additional information about the DA D-3 receptor. (C) Elsevier, Paris.
• Lin Chiu-Hong, Haadsma-Svensson Susanne R., Lahti Robert A., McCall Rober+, J. Med. Chem., 36 (1993) N 8, S 1053-1068
  作者：Lin Chiu-Hong, Haadsma-Svensson Susanne R., Lahti Robert A., McCall Rober+

  DOI：——

  日期：——
• (1,2N) AND (3,2N)-CARBOCYCLIC-2-AMINO TETRALIN DERIVATIVES
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP0482084B1

  公开（公告）日：1997-05-07