3-carbomethoxy-2-tetralone | 31202-22-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-carbomethoxy-2-tetralone
• 英文别名: 2-Oxo-tetralin-carbonsaeure-(3)-methylester；Methyl-2,3-tetraloncarboxylat；3-Oxo-1.2.3.4-tetrahydro-<2>naphthoesaeure-methylester；3-Oxo-tetralin-2-carbonsaeure-methylester；2,3-Tetraloncarbonsaeure-methylester；Methyl 3-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate；methyl 3-oxo-2,4-dihydro-1H-naphthalene-2-carboxylate
• CAS: 31202-22-9
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: WCODZXOMGDTGCX-UHFFFAOYSA-N

物化性质

• 熔点：
  123-124 °C
• 沸点：
  331.4±42.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  3-carbomethoxy-2-tetralone 以 乙醇 为溶剂， 反应 24.0h， 以76%的产率得到(2S,3S)-3-Hydroxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Selective synthesis of 1-, and 3-carbomethoxy 2-tetralol stereoisomers by microbial reduction of the corresponding tetralones

  摘要：

  The microbial reduction of beta-ketoesters derived from 2-tetralone has been shown to produce good yields of 2-hydroxy-1-carboxy- or 3-hydroxy-2-carboxyesters. Baker's yeast invariably affords a high enantiomeric purity cis-hydroxyester, while fungi strains may produce, sometimes exclusively, cis- or trans- complementary stereochemistries. From a general survey of the baker's yeast reduction of cyclic beta-ketoesters, a working model for predicting enantio- and diastereoselectivities of the reduction is proposed and discussed. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00389-8
• 作为产物：
  描述：

  重氮甲烷 、 碳酸镁 、 β-四氢萘酮 生成 3-carbomethoxy-2-tetralone
  参考文献：
  名称：

  Selective synthesis of 1-, and 3-carbomethoxy 2-tetralol stereoisomers by microbial reduction of the corresponding tetralones

  摘要：

  The microbial reduction of beta-ketoesters derived from 2-tetralone has been shown to produce good yields of 2-hydroxy-1-carboxy- or 3-hydroxy-2-carboxyesters. Baker's yeast invariably affords a high enantiomeric purity cis-hydroxyester, while fungi strains may produce, sometimes exclusively, cis- or trans- complementary stereochemistries. From a general survey of the baker's yeast reduction of cyclic beta-ketoesters, a working model for predicting enantio- and diastereoselectivities of the reduction is proposed and discussed. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00389-8

文献信息

• 一种医药中间体环烷烃并嘧啶二酮化合物的 合成方法
  申请人：中国海洋大学

  公开号：CN112028839B

  公开（公告）日：2022-04-12

  本发明提供了一种环烷烃并嘧啶二酮化合物的合成方法，属于有机合成技术领域。本发明所提供的方法为以2‑甲氧羰基环烷酮化合物为原料，在碱存在下与S‑甲基异硫脲硫酸盐在水中发生关环反应，反应完成后调节pH生成悬浊液，过滤得到2‑甲硫基‑4羟基环烷烃并嘧啶化合物粗品，粗品再在酸催化剂的存在下发生水解反应，反应完成后通过热滤、溶剂洗涤、真空浓缩、析晶、过滤、水洗、烘干等操作得到目标产物环烷烃并嘧啶二酮化合物。本发明的合成方法收率高、操作简便、对设备和环境友好，适用于环烷烃并嘧啶二酮化合物的高效合成。
• Synthesis and HIV-1 inhibitory properties of new tetrahydrobenzoquinazolinedione and tetrahydrobenzocycloheptenuracil derivatives and of their thioxo analogues
  作者：Marco Macchia、Guido Antonelli、Aldo Balsamo、Silvia Barontini、Federico Calvani、Daniela Gentili、Adriano Martinelli、Armando Rossello、Ombretta Turriziani、Ramon Tesoro

  DOI：10.1016/s0014-827x(99)00024-5

  日期：1999.4

  Some new tetrahydrobenzoquinazolinediones 2a-4a, tetrahydrobenzocycloheptenuracils 5a, 6a and their thioxo analogues 2b-6b were synthesized within a project aimed at obtaining new HIV-1 tricyclic inhibitors whose scaffold includes a pyrimidine and a phenyl ring, which are present in various HIV-1 non-nucleoside inhibitors. Among the tetrahydrobenzaquinazolinediones 2a-4a, compounds 3a and 4a, in which the tricyclic system is respectively in an angular or linear arrangement, proved to possess a HIV-1 inhibitory activity which was in the micromolar range, while compound 2a, in which the tricyclic system is in the angular arrangement opposite to that of 3a, was found to be completely inactive. As regards the tetrahydrobenzocycloheptenuracil derivatives (5a and 6a), only 5a showed an inhibitory activity similar to that of 3a and 4a. Furthermore, all thioxo analogues 2b-6b were found to be devoid of any activity. (C) 1999 Elsevier Science S.A. All rights reserved.
• US4692453A
  申请人：——

  公开号：US4692453A

  公开（公告）日：1987-09-08
• Selective synthesis of 1-, and 3-carbomethoxy 2-tetralol stereoisomers by microbial reduction of the corresponding tetralones
  作者：Cécile Abalain、Didier Buisson、Robert Azerad

  DOI：10.1016/0957-4166(96)00389-8

  日期：1996.10

  The microbial reduction of beta-ketoesters derived from 2-tetralone has been shown to produce good yields of 2-hydroxy-1-carboxy- or 3-hydroxy-2-carboxyesters. Baker's yeast invariably affords a high enantiomeric purity cis-hydroxyester, while fungi strains may produce, sometimes exclusively, cis- or trans- complementary stereochemistries. From a general survey of the baker's yeast reduction of cyclic beta-ketoesters, a working model for predicting enantio- and diastereoselectivities of the reduction is proposed and discussed. Copyright (C) 1996 Elsevier Science Ltd