3,4-Dihydro-6-methoxy-2-(pyrrolidin-1-yl)naphthalene | 20915-80-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,4-Dihydro-6-methoxy-2-(pyrrolidin-1-yl)naphthalene
• 英文别名: 1-(6-Methoxy-3,4-dihydro-2-naphthyl)pyrrolidin；1-(6-Methoxy-3,4-dihydronaphthalen-2-yl)-pyrrolidine；1-(6-methoxy-3,4-dihydro-2-naphthyl)pyrrolidine；3,4-dihydro-6-methoxy-2-pyrrolidinonapthalene；1-(3,4-dihydro-6-methoxynaphthalen-2-yl)-pyrrolidine；1-(6-methoxy-3,4-dihydronaphthalen-2-yl)pyrrolidine
• CAS: 20915-80-4
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: NBKWGVDIYHHCKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-Dihydro-6-methoxy-2-(pyrrolidin-1-yl)naphthalene 在 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 33.0h， 生成 3,4-dihydro-6-methoxy-1-(phenylmethyl)-2(1H)-naphthalenone
  参考文献：
  名称：

  α-Substituted N-(Sulfonamido)alkyl-β-aminotetralins:  Potent and Selective Neuropeptide Y Y5 Receptor Antagonists

  摘要：

  DOI：

  10.1021/jm990468g
• 作为产物：
  描述：

  四氢吡咯 、 6-甲氧基-3,4-二氢-1H-2-萘酮 在 montmorillonite K₁₀ Clay 作用下， 反应 0.1h， 以70%的产率得到3,4-Dihydro-6-methoxy-2-(pyrrolidin-1-yl)naphthalene
  参考文献：
  名称：

  Microwave-Induced Montmorillonite-Mediated Facile Synthesis of Enamines

  摘要：

  蒙脱石黏土介导的简单高产率合成方案，在微波条件下合成不同的烯胺，使用次级胺和酮。该方案非常便利，可在温和反应条件下、短时间内高产率地从环状胺与各种羰基化合物中获得烯胺。

  DOI：

  10.14233/ajchem.2020.22169

文献信息

• Carboxyarylindoles as nonsteroidal antiinflammatory agents
  作者：V. Brian Anderson、Marc N. Agnew、Richard C. Allen、Jeffrey C. Wilker、Howard B. Lassman、William J. Novick

  DOI：10.1021/jm00224a023

  日期：1976.2

  An extensive series of carboxyarylindoles has been evaluated for antiinflammatory activity in the carrageenin paw edema assay. The requirements for optimal antiinflammatory activity in this series are relatively specific: a central pyrrole nucleus with (a) a 3-carboxy-4-hydroxyphenyl moiety substituted directly on the nitrogen, (b) a 2-phenyl group (R2) with a substituent of low electronegativity,

  已经在角叉菜胶爪水肿试验中评估了一系列羧芳基吲哚的抗炎活性。此系列中最佳抗炎活性的要求是相对特定的：中心吡咯核具有（a）直接在氮上取代的3-羧基-4-羟基苯基部分，（b）具有取代基的2-苯基（R2）低电负性，（c）在3位（R3）上不存在取代基，和（d）在4,5位（X）上稠合的系统，该系统是亲脂的，准平面的，并且不与N发生空间相互作用-苯基。选择了一种衍生物3-（3-羧基-4-羟基苯基）-2-苯基-4,5-二氢-3H-苯并[e]吲哚（42）进行进一步研究。
• Bifunctional Brønsted Base Catalyst Enables Regio-, Diastereo-, and Enantioselective C_α-Alkylation of β-Tetralones and Related Aromatic-Ring-Fused Cycloalkanones
  作者：Iñaki Urruzuno、Odei Mugica、Mikel Oiarbide、Claudio Palomo

  DOI：10.1002/anie.201612332

  日期：2017.2.13

  The catalytic asymmetric synthesis of both α‐substituted and α,α‐disubstituted (quaternary) β‐tetralones through direct α‐functionalization of the corresponding β‐tetralone precursor remains elusive. A designed Brønsted base‐squaramide bifunctional catalyst promotes the conjugate addition of either unsubstituted or α‐monosubstituted β‐tetralones to nitroalkenes. Under these reaction conditions, not

  通过相应的β-四氢萘酮前体的直接α-官能化，α-取代的和α，α-二取代的（季）β-四氢萘酮的催化不对称合成仍然难以捉摸。设计的布朗斯台德碱-方酰胺双功能催化剂可促进未取代的或α-单取代的β-四氢萘酮与硝基烯烃的共轭加成反应。在这些反应条件下，不仅烯醇化和官能化仅在β-四氢萘酮的α-碳原子上发生，而且包括全碳四元中心的加合物也以高度非对映和对映选择性的方式形成。
• Hydrocinnamic acid derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US04883815A1

  公开（公告）日：1989-11-28

  Hydrocinnamic acid derivatives of the formula ##STR1## wherein one or two of the symbols R.sup.1 to R.sup.4 are halogen or methoxy and the others are hydrogen; R.sup.5 is hydrogen or phenyl; R.sup.6 is a residue of the formula ##STR2## R.sup.7 is (C.sub.1 -C.sub.4)-alkyl, (C.sub.2 -C.sub.5)-alkanoylamino-(C.sub.2 -C.sub.5)-alkyl, amino or (C.sub.1 -C.sub.4)-alkoxyphenyl; R.sup.8 and R.sup.9 each, independently, are hydrogen or (C.sub.1 -C.sub.4)-alkyl; R.sup.10 is hydrogen and R.sup.11 is hydroxy or R.sup.10 and R.sup.11 taken together are oxo; R.sup.12 is hydrogen, (C.sub.1 -C.sub.10)-alkyl, pyridylmethyl or carbamoylmethyl; R.sup.13 is hydrogen, (C.sub.1 -C.sub.4)-alkyl and R.sup.14 is hydrogen, (C.sub.1 -C.sub.4)-alkyl, pyridyl, phenyl-(C.sub.1 -C.sub.4)-alkyl, carboxy-(C.sub.1 -C.sub.4)-alkyl, carbamoyl-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy carbonyl-(C.sub.1 -C.sub.4)-alkyl, di-(C.sub.1 -C.sub.4)-alkoxy carbonyl-C.sub.2 -C.sub.5)-alky, piperidino-C.sub.2 -C.sub.4)-alkyl or halopyridinecarboxamido-(C.sub.2 -C.sub.4)-alkyl or R.sup.13 and R.sup.14 taken together with the nitrogen atom are 4-(C.sub.1 -C.sub.4)-alkyl-piperazin-1-yl, as well as pharmaceutically acceptable salts of basic compounds of formula I with acids or of acidic compounds of formula I with bases are described. The compounds of formula I and their pharmaceutically acceptable salts are suitable for the control or prevention of cerebral insufficiency or for the improvement of cognitive functions.

  公式为##STR1##的羟肉桂酸衍生物，其中符号R.sup.1至R.sup.4中的一个或两个是卤素或甲氧基，其余为氢；R.sup.5为氢或苯基；R.sup.6为##STR2##的残基；R.sup.7为(C.sub.1 -C.sub.4)-烷基，(C.sub.2 -C.sub.5)-辛酰胺基-(C.sub.2 -C.sub.5)-烷基，氨基或(C.sub.1 -C.sub.4)-烷氧基苯基；R.sup.8和R.sup.9各自独立地为氢或(C.sub.1 -C.sub.4)-烷基；R.sup.10为氢，R.sup.11为羟基或R.sup.10和R.sup.11一起为氧代；R.sup.12为氢，(C.sub.1 -C.sub.10)-烷基，吡啶甲基或氨甲酰甲基；R.sup.13为氢，(C.sub.1 -C.sub.4)-烷基，R.sup.14为氢，(C.sub.1 -C.sub.4)-烷基，吡啶，苯基-(C.sub.1 -C.sub.4)-烷基，羧基-(C.sub.1 -C.sub.4)-烷基，氨甲酰-(C.sub.1 -C.sub.4)-烷基，(C.sub.1 -C.sub.4)-烷氧基羰基-(C.sub.1 -C.sub.4)-烷基，二-(C.sub.1 -C.sub.4)-烷氧基羰基-C.sub.2 -C.sub.5)-烷基，哌哆啶-C.sub.2 -C.sub.4)-烷基或卤代吡啶基羧酰胺基-(C.sub.2 -C.sub.4)-烷基或R.sup.13和R.sup.14与氮原子一起为4-(C.sub.1 -C.sub.4)-烷基-哌嗪-1-基，以及公式I的碱性化合物的药学上可接受的盐与酸或公式I的酸性化合物的药学上可接受的盐与碱描述。公式I的化合物及其药学上可接受的盐适用于控制或预防脑部供血不足或改善认知功能。
• N-substituted aminotetralins as ligands for the neuropeptide Y Y5
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：US06140354A1

  公开（公告）日：2000-10-31

  .beta.-Aminotetralin derivatives of the formula: ##STR1## which are ligands for the neuropeptide Y Y5 (NPY5) receptor, methods of preparation and pharmaceutical compositions containing a .beta.-aminotetralin derivative as the active ingredient are described. The .beta.-aminotetralins are useful in the treatment of disorders and diseases associated with NPY receptor subtype Y5.

  该公式的.beta.-氨基四氢萘衍生物：##STR1##，它们是神经肽Y Y5（NPY5）受体的配体，描述了制备方法和含有.beta.-氨基四氢萘衍生物作为活性成分的药物组合物。这些.beta.-氨基四氢萘在治疗与NPY受体亚型Y5相关的疾病和疾病中很有用。
• [3 + 3]-Carbocyclizations of nitroallylic esters and enamines with stereoselective formation of up to six new stereogenic centers
  作者：Dieter Seebach、Martin Missbach、Giorgio Calderari、Martin Eberle

  DOI：10.1021/ja00177a026

  日期：1990.10

  and intermediates, which can be trapped under certain conditions, as well as previous investigations of single steps of the in situ reaction sequence involved in the carbocyclization are used to arrive at a tentative proposal for the steric course of these steps: (i) intermolecular coupling of the trigonal centers of enamine and nitroolefin with preferred relative topicity like, (ii) intramolecular coupling

  讨论了导致观察到的产物的复杂反应序列的机制。可以在某些条件下捕获的产物和中间体的结构，以及先前对参与碳环化的原位反应序​​列的单个步骤的研究，用于得出这些步骤的空间过程的初步建议： (i) 烯胺和硝基烯烃的三角中心的分子间偶联，具有优选的相对局部性，(ii) 中间体烯胺中的三角中心的分子内偶联，(iii) 硝基阴离子部分的质子化，和 (iv) 的质子化烯胺（在单环产品的情况下）