1-oxo-1,2,3,4-tetrahydro-2-naphthaleneacetic acid ethyl ester | 41059-51-2

• 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-oxo-1,2,3,4-tetrahydro-2-naphthaleneacetic acid ethyl ester
• 英文别名: ethyl 2-[2-(1,2,3,4-tetrahydro-1-oxonaphthalenyl)]acetate；1-oxo-1,2,3,4-tetrahydro-2-naphthaleneacetic ethyl ester；ethyl 2-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetate；ethyl (1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetate；ethyl 1-oxo-1,2,3,4-tetrahydronaphthyl-2-acetate；1-Oxo-tetralin-2-essigsaeure-diethylester；ethyl 2-(1-oxo-3,4-dihydro-2H-naphthalen-2-yl)acetate
• CAS: 41059-51-2
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: UXHVZHOONBSRIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-oxo-1,2,3,4-tetrahydro-2-naphthaleneacetic acid ethyl ester 在 氢氧化钾 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 4-[2-(1-Oxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-acetyl]-piperazine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and Affinities for Dopamine (D2) and 5-Hydroxytryptamine (5-HT2A Receptors of 1-(Benzoylpropyl)-4-(1-oxocycloalkyl-2-ethyl)- piperazines as Cyclic Butyrophenone Derivatives.

  摘要：

  从苯乙酸或噻吩环烷基乙酸开始，我们制备了一系列 1-(3-对氟苯甲酰基丙基)-4-(1-氧代-苯或噻吩环烷基-2-乙基)哌嗪 8a-e，其中含有半刚性和线性丁基苯酮药效团。这些化合物与多巴胺（D2）和 5-羟色胺（5-HT2A）受体的亲和力在体外受体结合实验和功能实验中进行了评估。5-HT2A/D2受体的pKi比值可用于快速筛选新化合物和评估诱发锥体外系症状的可能性；比值为≥-1.12（Meltzer比值）可预测非典型抗精神病药物的特征。新分子的比值范围为 0.96-1.11，而氟哌啶醇的比值为 0.93。比值为 1.11 的 2-哌嗪基乙基硫代四氢萘酮衍生物 8d（QF 0506B）是活性最强的化合物。

  DOI：

  10.1248/cpb.44.534
• 作为产物：
  描述：

  ethyl 5-{2-[(4-cyanophenyl)thiocarbonyl]phenyl}-2-pentenoate 在 1,4,8,11-tetraazacyclotetradecane based Ni(II) 、 四乙基对甲苯磺酸铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以44%的产率得到1-oxo-1,2,3,4-tetrahydro-2-naphthaleneacetic acid ethyl ester
  参考文献：
  名称：

  Cyclization of Aryl Acyl Radicals Generated from S-(4-Cyano)phenyl Thiolesters by a Nickel Complex Catalyzed Electroreduction

  摘要：

  Aromatic acyl radicals generated from S-(4-cyano)phenyl 2-alkenylthiobenzoate by a nickel complex catalyzed electroreduction undergo 5- and 6-exo cyclization to give 1-indanone and dihydro-1-naphthalenone derivatives, respectively.

  DOI：

  10.1021/jo0268512

文献信息

• Intermolecular Addition Reaction to Alkenes of Acylmolybdenum Complexes Generated by Oxidative Addition of Aryl or Alkenyl Halides with Molybdenum(0) Carbonyl Complexes
  作者：Nobuharu Iwasawa、Kenichiro Sangu、Toru Watanabe、Jun Takaya

  DOI：10.1055/s-2007-973858

  日期：2007.4

  Acylmolybdenum species, generated by oxidative addition of aryl or alkenyl halides with molybdenum(0) carbonyl complex followed by carbon monoxide insertion, added to various kinds of alkenes intermolecularly to give simple addition products in good yields without formation of carbonylative Heck-type products.

  酰基钼物种，通过芳基或烯基卤化物与钼 (0) 羰基络合物的氧化加成，然后插入一氧化碳，分子间添加到各种烯烃中，以良好的收率得到简单的加成产物，而不会形成羰基化的 Heck 型产物。
• Efficient Synthesis of γ‐Keto Esters from Enamines and EDA
  作者：Dan Huang、Ming Yan、Wei‐Jie Zhao、Qi Shen

  DOI：10.1081/scc-200050387

  日期：2005.3.1

  Abstract The reaction of enamines with ethyl diazoacetate (EDA) catalyzed by dirhodium and copper complexes provided γ‐keto esters in good yields. The influences of catalyst, reaction solvent, temperature, and structure of enamines on this transformation were investigated.

  摘要 由二铑和铜配合物催化的烯胺与重氮乙酸乙酯 (EDA) 的反应以良好的收率提供了 γ-酮酯。考察了催化剂、反应溶剂、温度和烯胺结构对这种转化的影响。
• Fluoride Anions in Self-Assembled Chiral Cage for the Enantioselective Protonation of Silyl Enol Ethers
  作者：Sushovan Paladhi、Yidong Liu、B. Senthil Kumar、Min-Jung Jung、Sang Yeon Park、Hailong Yan、Choong Eui Song

  DOI：10.1021/acs.orglett.7b01429

  日期：2017.6.16

  The potential of Song’s chiral oligoethylene glycols (oligoEGs) as catalysts was explored in the enantioselective protonation of trimethylsilyl enol ethers in combination with alkali metal fluoride (KF and CsF) and in the presence of a proton source. Highly enantioselective protonations of various silyl enol ethers of α-substituted tetralones were achieved, producing chiral α-substituted tetralones

  Song的手性低聚乙二醇（oligoEGs）作为催化剂的潜力已在三甲基甲硅烷基烯醇醚与碱金属氟化物（KF和CsF）结合以及质子源存在下的对映选择性质子化中得到了探索。获得了α-取代的四氢萘酮的各种甲硅烷基烯醇醚的高度对映选择性质子化，以完全转化并具有高达99％的ee产生了手性α-取代的四氢萘酮。已建立的协议已成功扩展到生物相关的手性α-取代的苯并二氢吡喃酮和硫代苯并二氢吡喃酮衍生物的合成。
• Development of a Chiral Bis(guanidino)iminophosphorane as an Uncharged Organosuperbase for the Enantioselective Amination of Ketones
  作者：Tadahiro Takeda、Masahiro Terada

  DOI：10.1021/ja408296h

  日期：2013.10.16

  Chiral bis(guanidino)iminophosphoranes were designed and synthesized as chiral uncharged organosuperbase catalysts that facilitate activation of lessacidic pro-nucleophiles. The newly developed bis(guanidino)iminophosphoranes, which possess the highest basicity among chiral organocatalysts reported to date, were proven to be a superb class of chiral organosuperbases by reaction of azodicarboxylates with 2-alkyltetralones and their analogues as the less acidic pro-nucleophiles.
• Asymmetric Intramolecular Crossed-Benzoin Reactions by N-Heterocyclic Carbene Catalysis
  作者：Dieter Enders、Oliver Niemeier、Tim Balensiefer

  DOI：10.1002/anie.200503885

  日期：2006.2.20