7-bromo-1-oxo-1,2,3,4-tetrahydro-2-naphthoic acid ethyl ester | 914262-72-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-bromo-1-oxo-1,2,3,4-tetrahydro-2-naphthoic acid ethyl ester
• 英文别名: ethyl 7-bromo-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate；ethyl 7-bromo-1-oxo-3,4-dihydro-2H-naphthalene-2-carboxylate
• CAS: 914262-72-9
• 化学式: C₁₃H₁₃BrO₃
• 分子量: 297.148
• InChiKey: NVPPZACQBBTTSF-UHFFFAOYSA-N

物化性质

• 熔点：
  67.6 °C(Solv: ligroine (8032-32-4))
• 沸点：
  381.5±42.0 °C(Predicted)
• 密度：
  1.463±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 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：

  7-bromo-1-oxo-1,2,3,4-tetrahydro-2-naphthoic acid ethyl ester 在 盐酸 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 、 oil 为溶剂， 反应 45.25h， 生成 7-bromo-2-((1-(2,2-difluoroethyl)piperidin-4-yl)methyl)-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  [EN] COMPOUNDS FOR TREATING NEURODEGENERATIVE DISEASES
  [FR] COMPOSÉS POUR TRAITER DES MALADIES NEURODÉGÉNÉRATIVES

  摘要：

  这项发明提供了一种新型的Formula α的螺环四氢萘化合物，可以抑制APP的β-分泌酶裂解，并且可用作治疗神经退行性疾病的治疗剂。

  公开号：

  WO2011123674A1
• 作为产物：
  描述：

  3-(4-溴苯甲酰)丙酸 在 氢氧化钾 、 PPA 、 sodium hydride 、 肼 作用下， 以 苯 、 三乙二醇 为溶剂， 反应 5.33h， 生成 7-bromo-1-oxo-1,2,3,4-tetrahydro-2-naphthoic acid ethyl ester
  参考文献：
  名称：

  Dicationic DNA-targeted antiprotozoal agents: Naphthalene replacement of benzimidazole

  摘要：

  A series of naphthalene analogues of highly active benzimidazole diamidines were synthesized using sequential Stille and Suzuki coupling reactions for preparation of the bis-nitrile intermediates. All of the diamidines showed strong DNA affinities as judged by high Delta T-m values with poly(dA-dT). The dicationic compounds were quite active in vitro versus Trypanosoma brucei rhodesiense (T. b. r.) exhibiting IC50 values ranging from 4 to 98 nM. These compounds were also active versus Plasmodium falciparum (P. f) giving IC50 values ranging from 4 to 33 nM. Two of the compounds showed good activity in vivo in the STIB900 model for acute African trypanosomiasis; one gave 3/4 cures and the other gave 4/4 cures on ip dosage of 20 mg/kg for 4 days. The amidoxime prodrugs of the naphthalene analogues were essentially ineffective. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.024
• 作为试剂：
  描述：

  、 萘 、 苯并咪唑 、 碳酸二乙酯 、 sodium;hydride 、 7-溴-3,4-二氢萘-1(2H)-酮 、 氮气 在 7-bromo-1-oxo-1,2,3,4-tetrahydro-2-naphthoic acid ethyl ester 、 氮气 、 ice 、 乙酸乙酯 、 Brine 、 magnesium sulfate 、 乙醇 作用下， 以 甲苯 、 溶剂黄146 为溶剂， 反应 4.33h， 以giving ethyl 7-bromo-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate (5.2 g, 77% yield)的产率得到7-bromo-1-oxo-1,2,3,4-tetrahydro-2-naphthoic acid ethyl ester
  参考文献：
  名称：

  COMPOUNDS FOR TREATING NEURODEGENERATIVE DISEASES

  摘要：

  本发明提供了一种新型的螺四氢萘酚化合物，其化学式为α，可以抑制β-分泌酶对APP的切割，并且可用作治疗神经退行性疾病的治疗剂。

  公开号：

  US20120065195A1

文献信息

• <i>N,N′</i>-Dioxide-Magnesium Ditriflate Complex-Catalyzed Asymmetric α-Hydroxylation of β-Keto Esters and β-Keto Amides
  作者：Chengkai Yin、Weidi Cao、Lili Lin、Xiaohua Liu、Xiaoming Feng

  DOI：10.1002/adsc.201300335

  日期：2013.7.8

  The highly catalytic asymmetric α‐hydroxylation of 1‐tetralone‐derived β‐keto esters and β‐keto amides using tert‐butyl hydroperoxide (TBHP) as the oxidant was realized by a chiral N,N′‐dioxide‐magnesium ditriflate [Mg(OTf)2] complex. A series of corresponding chiral α‐hydroxy dicarbonyl compounds was obtained in excellent yields (up to 99%) with excellent enantioselectivities (up to 98% ee). The products

  使用叔丁基氢过氧化物（TBHP）作为氧化剂，对1-四氢萘酮衍生的β-酮酯和β-酮酰胺进行高度催化的不对称α-羟基化反应，是通过手性N，N'-二氧化物-三氟甲磺酸镁[Mg（ OTf）2 ]复杂。以优异的收率（最高99％）和优异的对映选择性（最高98％ee）获得了一系列相应的手性α-羟基二羰基化合物。产物易于转化为有用的结构单元，并且首次以不对称催化方式获得了道诺霉素的前体。
• Highly enantioselective α-chlorination of cyclic β-ketoesters catalyzed by N,N′-Dioxide using NCS as the chlorine source
  作者：Yunfei Cai、Wentao Wang、Ke Shen、Jun Wang、Xiaolei Hu、Lili Lin、Xiaohua Liu、Xiaoming Feng

  DOI：10.1039/b922769e

  日期：——

  A simple and highly efficient N,N′-dioxide organocatalyst system was developed for the asymmetric α-chlorination of cyclic β-ketoesters using easily available NCS as the chlorine source to provide a series of optically active α-chloro-β-ketoesters in excellent yields with 90–98% ee.

  开发了一种简单且高效的N,N′-二氧化物有机催化剂系统，利用易得的NCS作为氯源，针对循环β-酮酯的非对称α-氯化反应，提供了一系列光学活性的α-氯-β-酮酯，其产率极佳，光学纯度为90–98% ee。
• Construction of Polycyclic β-Ketoesters Using a Homoconjugate Addition/Decarboxylative Dieckmann Annulation Strategy
  作者：Zhiwei Chen、Allen Y. Hong、Xin Linghu

  DOI：10.1021/acs.joc.8b00754

  日期：2018.6.1

  arene-fused cyclic β-ketoesters from 2-iodoaryl esters and 1,1-cyclopropane diesters is detailed. The synthetic method takes advantage of a CuI·SMe2-mediated homoconjugate addition followed by a decarboxylative Dieckmann cyclization to afford valuable polycyclic building blocks. Various iodoaryl esters and 1,1-cyclopropane diesters were evaluated, and the limitations of both reactions are discussed. Several

  详细说明了由2-碘芳基酯和1,1-环丙烷二酯构建芳烃稠合的环状β-酮酸酯。该合成方法利用了CuI·SMe 2介导的均聚物加成，然后进行脱羧Dieckmann环化的优势，从而提供了有价值的多环结构单元。评价了各种碘代芳基酯和1,1-环丙烷二酯，并讨论了两个反应的局限性。详细介绍了几种机械探针，并介绍了其综合应用。
• [EN] COMPOUNDS FOR TREATING NEURODEGENERATIVE DISEASES<br/>[FR] COMPOSÉS POUR TRAITER DES MALADIES NEURODÉGÉNÉRATIVES
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2011123674A1

  公开（公告）日：2011-10-06

  The invention provides novel spirotetrahydronaphthalene compounds of Formula α that inhibit β-secretase cleavage of APP and are useful as therapeutic agents for treating neurodegenerative diseases.

  这项发明提供了一种新型的Formula α的螺环四氢萘化合物，可以抑制APP的β-分泌酶裂解，并且可用作治疗神经退行性疾病的治疗剂。
• Dicationic DNA-targeted antiprotozoal agents: Naphthalene replacement of benzimidazole
  作者：Sarah Chackal-Catoen、Yi Miao、W. David Wilson、Tanja Wenzler、Reto Brun、David W. Boykin

  DOI：10.1016/j.bmc.2006.07.024

  日期：2006.11

  A series of naphthalene analogues of highly active benzimidazole diamidines were synthesized using sequential Stille and Suzuki coupling reactions for preparation of the bis-nitrile intermediates. All of the diamidines showed strong DNA affinities as judged by high Delta T-m values with poly(dA-dT). The dicationic compounds were quite active in vitro versus Trypanosoma brucei rhodesiense (T. b. r.) exhibiting IC50 values ranging from 4 to 98 nM. These compounds were also active versus Plasmodium falciparum (P. f) giving IC50 values ranging from 4 to 33 nM. Two of the compounds showed good activity in vivo in the STIB900 model for acute African trypanosomiasis; one gave 3/4 cures and the other gave 4/4 cures on ip dosage of 20 mg/kg for 4 days. The amidoxime prodrugs of the naphthalene analogues were essentially ineffective. (c) 2006 Elsevier Ltd. All rights reserved.