(+/-)-5,8-dimethoxy-2-hydroxy-2-(1'-hydroxyethyl)-1,2,3,4-tetrahydronaphthalene | 81452-15-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (+/-)-5,8-dimethoxy-2-hydroxy-2-(1'-hydroxyethyl)-1,2,3,4-tetrahydronaphthalene
• 英文别名: (+/-)-2-hydroxyethyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene；2-(1-hydroxyethyl)-5,8-dimethoxy-3,4-dihydro-1H-naphthalen-2-ol
• CAS: 81452-15-5
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: WYKATIKHEGTVHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-5,8-dimethoxy-2-hydroxy-2-(1'-hydroxyethyl)-1,2,3,4-tetrahydronaphthalene 在 三氯化铝 、 silver carbonate 、 sodium chloride 作用下， 以 苯 为溶剂， 反应 2.08h， 生成 4-demethoxy-7-deoxydaunomycinone
  参考文献：
  名称：

  Rao, A. V. Rama; Deshpande, V. H.; Sathaye, K. M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 697 - 702

  摘要：

  DOI：
• 作为产物：
  描述：

  2-bromo-5,8-dimethoxy-1-tetralone 在 lithium aluminium tetrahydride 作用下， 生成 (+/-)-5,8-dimethoxy-2-hydroxy-2-(1'-hydroxyethyl)-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Synthesis in the Field of Natural Products of Biological Relevance

  摘要：

  AbstractThe chemical manipulation of the aminosugar, daunosamine, has resulted in the development of new interesting doxorubicin analogues, namely 4′‐epi‐ and 4′‐deoxydoxorubicin, whereas the total synthesis of new aglycones has provided new structural types of the anthracyclines. In the field of beta‐lactams, efforts aimed to the discovery of original anti‐infective compounds have led to the synthesis of novel “penem” derivatives starting from methyl penicillinate.

  DOI：

  10.1002/bscb.19820911207

文献信息

• 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。
• Synthesis in the Field of Natural Products of Biological Relevance
  作者：Federico Arcamone

  DOI：10.1002/bscb.19820911207

  日期：——

  AbstractThe chemical manipulation of the aminosugar, daunosamine, has resulted in the development of new interesting doxorubicin analogues, namely 4′‐epi‐ and 4′‐deoxydoxorubicin, whereas the total synthesis of new aglycones has provided new structural types of the anthracyclines. In the field of beta‐lactams, efforts aimed to the discovery of original anti‐infective compounds have led to the synthesis of novel “penem” derivatives starting from methyl penicillinate.
• A short synthesis of two chiral anthracycline AB synthons
  作者：Herbert L. Holland、Peter Viski

  DOI：10.1021/jo00017a046

  日期：1991.8
• SODEOKA, MIKIKO;IIMORI, TAKAMASA;SHIBASAKI, MASAKATSU, TETRAHEDRON LETT., 1985, 26, N 52, 6497-6500
  作者：SODEOKA, MIKIKO、IIMORI, TAKAMASA、SHIBASAKI, MASAKATSU

  DOI：——

  日期：——
• TAMOTO, KATSUMI;TERASHIMA, SHIRO, CHEM. AND PHARM. BULL., 1984, 32, N 11, 4340-4349
  作者：TAMOTO, KATSUMI、TERASHIMA, SHIRO

  DOI：——

  日期：——