5,8-二甲氧基-3,4-二氢萘-2-羧酸 | 68569-96-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 5,8-二甲氧基-3,4-二氢萘-2-羧酸
• 英文名称: 5,8-dimethoxy-3,4-dihydro-2-naphthoic acid
• 英文别名: 3,4-Dihydro-5,8-dimethoxy-2-naphthoic acid；5,8-Dimethoxy-3,4-dihydronaphthalin-2-carbonsaeure；5,8-Dimethoxy-3,4-dihydronaphthalene-2-carboxylic acid
• CAS: 68569-96-0
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: DRSUGRQPMWIEHB-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：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,8-二甲氧基-3,4-二氢萘-2-羧酸 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 1-(5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthalenyl)-1-ethanone
  参考文献：
  名称：

  Rao, M. Vishnumurthi; Bhatt, M. Vivekananda, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 6, p. 487 - 488

  摘要：

  DOI：
• 作为产物：
  描述：

  Ethyl 3,4-dihydro-5,8-dimethoxy-2-naphthoate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 5,8-二甲氧基-3,4-二氢萘-2-羧酸
  参考文献：
  名称：

  Novel process for asymmetric synthesis of optically active

  摘要：

  一种用于不对称合成光学活性2-烷酰基-1,2,3,4-四氢-2-萘酚化合物的过程，其化学式为：从L-脯氨酸或其酯和以下化学式的羧酸：或其反应性衍生物通过以下中间化合物依次进行：

  公开号：

  US04212828A1

文献信息

• Novel process for asymmetric synthesis of optically active
  申请人：Sumitomo Chemical Company, Limited

  公开号：US04212828A1

  公开（公告）日：1980-07-15

  A process for asymmetric synthesis of optically active 2-alkanoyl-1,2,3,4-tetrahydro-2-naphthol compounds of the formula: ##STR1## from L-proline or its ester and the following carboxylic acid of the formula: ##STR2## or its reactive derivative through the following intermediary compounds in order: ##STR3##

  一种用于不对称合成光学活性2-烷酰基-1,2,3,4-四氢-2-萘酚化合物的过程，其化学式为：从L-脯氨酸或其酯和以下化学式的羧酸：或其反应性衍生物通过以下中间化合物依次进行：
• Development of a novel synthetic route to optically active anthracyclinones: Preliminary synthesis of the racemic key intermediate.
  作者：NORIHIKO TANNO、SHIRO TERASHIMA

  DOI：10.1248/cpb.31.811

  日期：——

  In order to develop a novel synthetic route to a key synthetic intermediate ((R)-(-)-3) for optically active anthracyclinones (2a-d), preparation of the racemic intermediate ((±)-3) from the α, β-unsaturated ketone (6), obtainable from the α, β-unsaturated acid (5) or the 2-tetralone (11), was attempted according to the designed synthetic scheme. Since epoxidation of the racemic allylic alcohol ((±)-7) produced by reduction of 6, followed by reductive cleavage of the epoxides ((±)-8a, b) and oxidation of the vicinal-diol ((±)-9a), was found to readily give the desired (±)-3 in good overall yield, optically pure (R)-(-)-3 should be obtainable from 6 if 6 can be asymmetrically reduced to afford (S)-7 in a high optical yield. The racemic ketone ((±)-3) was further transformed to (±)-7-deoxy-4-demethoxy-daunomycinone dimethyl ether ((±)-13), from which racemic 4-demethoxyanthracyclinone ((±)-2c, d) could be elaborated.

  为了开发出一条通向光学活性蒽环类化合物（2a-d）的关键合成中间体（(R)-(-)-3）的新合成路线，我们根据设计的合成方案，尝试从α，β-不饱和酮（6）制备外消旋中间体（(±)-3），该中间体可从α，β-不饱和酸（5）或 2-四氢萘酮（11）中获得。由于发现通过还原 6 生成的外消旋烯丙基醇（(±)-7）的环氧化反应，随后环氧化物（(±)-8a, b）的还原裂解和沧醛二醇（(±)-9a）的氧化反应很容易得到所需的(±)-3，而且总收率很高，因此如果 6 可以不对称地还原，以高光学收率得到(S)-7，那么就可以从 6 得到光学纯度为(R)-(-)-3。外消旋酮（(±)-3）进一步转化为(±)-7-脱氧-4-去甲氧基-金霉素酮二甲醚（(±)-13），并由此制备外消旋 4-去甲氧基蒽环酮（(±)-2c, d）。
• Modified aluminium hydrides, their preparation and their use in reducing acetylnaphthalene derivatives
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0035355A2

  公开（公告）日：1981-09-09

  A modified lithium aluminium hydride type reducing agent is useful for reducing organic compounds having a carbonyl group-(ketone group of aldehyde group) in their structure to the corresponding alcohols. It is obtained by reacting one equivalent of lithium aluminium hydride with one equivalent of an optically active N-substituted ephedrine of the formula, (wherein R, is a Ci-C4 alkyl group or benzyl group and Ph is phenyl group) and two equivalents of an N-substituted aniline of the formula, (wherein R2 is a C1-C4 alkyl group or phenyl group, and Ph is phenyl group). The reducing agent is particularly useful for reducing 2-acetyl-5, 8-dimethoxy-3, 4-dihydronaphthalene to the corresponding 2-(1'-hydroxy)ethyl compound, and, by selecting a particular modified aluminium hydride the unsymmetrical ketone can be reduced to selectively produce either an alcohol in which the asymmetric carbon atom bonded to the hydroxy group is in R-configuration or an alcohol in which said asymmetric carbon atom is in S-configuration.

  一种改性氢化锂铝型还原剂可用于将结构中含有羰基（酮基或醛基）的有机化合物还原成相应的醇类。它是通过将 1 个当量的氢化锂铝与 1 个当量的光学活性 N-取代麻黄碱反应得到的，其化学式为 (其中 R 为 Ci-C4 烷基或苄基，Ph 为苯基） 和两个等量的 N-取代苯胺，其式为 (其中 R2 为 C1-C4 烷基或苯基，Ph 为苯基）。 还原剂特别适用于将 2-乙酰基-5，8-二甲氧基-3，4-二氢萘还原成相应的 2-（1'-羟基）乙基化合物，通过选择特定的改性氢化铝，可以将不对称酮还原，选择性地生成与羟基键合的不对称碳原子为 R 构型的醇或所述不对称碳原子为 S 构型的醇。
• A novel synthesis of (±)-2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthol, a key intermediate for the synthesis of anthracyclinones
  作者：Shiro Terashima、Norihiko Tanno、Kenji Koga

  DOI：10.1016/s0040-4039(00)78596-0

  日期：1980.1
• A high yield synthesis of (±)-5,8-dimethoxy-2-α-hydroxyethyl-3,4-dihydronaphthalene, a key intermediate in anthracyclinone synthesis
  作者：M.Parameswara Reddy and G.S. Krishna^Rao

  DOI：10.1016/s0040-4039(01)81954-7

  日期：1981.1