(+/-)-1,2,3,4-tetrahydro-2-oxo-1-naphthaleneacetic acid methyl ester | 7531-31-9

• 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-2-oxo-1-naphthaleneacetic acid methyl ester
• 英文别名: methyl 2-(1-(1,2,3,4-tetrahydro-2-oxonaphthalenyl))acetate；2-Oxo-1-methoxycarbonyl-tetrahydronaphthalin；1-Naphthaleneacetic acid, 1,2,3,4-tetrahydro-2-oxo-, methyl ester；methyl 2-(2-oxo-3,4-dihydro-1H-naphthalen-1-yl)acetate
• CAS: 7531-31-9
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: AVLHEBLMJQSCNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-1,2,3,4-tetrahydro-2-oxo-1-naphthaleneacetic acid methyl ester 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 7.5h， 生成 cis-(+/-)-2,3,3a,4,5,9b-hexahydro-3-n-propyl-1H-benzindole
  参考文献：
  名称：

  中枢作用的血清素和多巴胺能药物。1. 2,3,3a，4,5,9b-六氢-1H-苯并[e]吲哚衍生物的合成及构效关系。

  摘要：

  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

  DOI：

  10.1021/jm00060a014
• 作为产物：
  描述：

  methyl 3-<2-<3-oxo-3-(phenylseleno)propyl>phenyl>-2-propenoate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以94%的产率得到(+/-)-1,2,3,4-tetrahydro-2-oxo-1-naphthaleneacetic acid methyl ester
  参考文献：
  名称：

  Acyl radicals: intermolecular and intramolecular alkene addition reactions

  摘要：

  A full study of the use of phenyl selenoesters as precursors to acyl radicals and their subsequent participation in intermolecular and intramolecular alkene addition reactions is detailed. Primary alkyl-, vinyl-, and aryl-substituted acyl radicals generated by Bu3SnH treatment of the corresponding phenyl selenoesters participate cleanly in intermolecular addition reactions with alkenes bearing electron-withdrawing or radical-stabilizing substituents at rates that exceed those of the potentially competitive decarbonylation or reduction. Similarly, their intramolecular addition to activated or unactivated alkenes proceeds without significant competitive reduction or decarbonylation and at rates generally greater-than-or-equal-to 1 x 10(6) s-1 with some occurring at rates greater-than-or-equal-to 3 x 10(7) s-1. Consistent with their behavior in intermolecular addition reactions, the 5-exo-trig cyclizations of secondary and tertiary alkyl-substituted acyl radicals to an unactivated olefin acceptor may be accompanied by varying degrees of decarbonylation, even under low-temperature free-radical reaction conditions. Studies are presented which suggest that the intramolecular additions of acyl radicals to alkenes under the conditions detailed herein may be regarded as irreversible, kinetically controlled processes which exhibit regioselectivity that is predictable based on well-established empirical rules set forth for the analogous free-radical cyclization reactions of alkyl radicals.

  DOI：

  10.1021/jo00031a021

文献信息

• (1,2N) and (3,2N)-carbocyclic-2-amino tetralin derivatives
  申请人：The Upjohn Company

  公开号：US05491236A1

  公开（公告）日：1996-02-13

  This invention is therapeutically useful tetralins and pharmaceutically acceptable acid addition salts thereof of the formula ##STR1## wherein R, R.sub.1 and A are as defined in claim 1. These compounds are useful to treat central nervous system disorders.

  这项发明是治疗上有用的四氢萘类化合物及其药学上可接受的酸盐，其化学式为##STR1##其中R、R.sub.1和A的定义如权利要求书中所述。这些化合物可用于治疗中枢神经系统疾病。
• Acyl radicals: functionalized free radicals for intramolecular cyclization reactions
  作者：Dale L. Boger、Robert J. Mathvink

  DOI：10.1021/jo00249a053

  日期：1988.7
• 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：——
• BOGER, D. L.;MATHVINK, R. J., J. ORG. CHEM., 53,(1988) N 14, 3377-3379
  作者：BOGER, D. L.、MATHVINK, R. J.

  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