(+/-)-2-acetyl-2-hydroxy-1,2,3,4-tetrahydro-5,8-dimethoxynaphthalene | 33628-85-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (+/-)-2-acetyl-2-hydroxy-1,2,3,4-tetrahydro-5,8-dimethoxynaphthalene
• 英文别名: 2-Acetyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene；(+/-)-2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthol；(+/-)-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthol；2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthol；2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphtol；2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydro-2-napthol；1-(2-hydroxy-5,8-dimethoxy-3,4-dihydro-1H-naphthalen-2-yl)ethanone
• CAS: 33628-85-2
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: ZSXULPOFXAGSMB-UHFFFAOYSA-N

物化性质

• 熔点：
  100-102 °C
• 沸点：
  442.4±45.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (+/-)-2-acetyl-2-hydroxy-1,2,3,4-tetrahydro-5,8-dimethoxynaphthalene 在 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 三氯化铝 、 偶氮二异丁腈 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 四氯化碳 、 二氯甲烷 、 硝基苯 、 苯 为溶剂， 反应 18.5h， 生成 (7S,9S)9-乙酰基-7,8,9,10-四氢-6,7,9,11-四羟基-5,12-并四苯二酮
  参考文献：
  名称：

  Facile Total Syntheses of Idarubicinone‐7‐β‐D‐glucuronide: Convenient Preparations of AB‐Ring Synthon Using Some Carboxylic Acid Derivatives

  摘要：

  Regiospecific syntheses of idarubicinone coupled with D-glucuronic acid are described. Cyclization of dimethoxybenzene with carboxylic acid derivatives in polyphosphoric acid (PPA) in one step afforded the naphthalenones 7, which were transformed to the (+/-)-idarubicinone 3b by general methods. Esterification of (+/-)-3b with (S)-(+)-O-acetylmandelic acid with subsequent separation and deprotection gave (+)-3b and (-)-3b. Reaction of separated two stereoisomers with acetobromo-alpha-D-glucuronic acid methyl ester respective followed by hydrolysis using lithium hydroxide and amberite cation exchange resin furnished two kinds of idarubicinone-7-beta-D-glucuronide (20 and 21) that are coupled at C-7 position of idarubicinone.

  DOI：

  10.1081/scc-120030758
• 作为产物：
  描述：

  (+/-)-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid 在 aluminium amalgam 、 sodium hydride 、 乙酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 23.0h， 生成 (+/-)-2-acetyl-2-hydroxy-1,2,3,4-tetrahydro-5,8-dimethoxynaphthalene
  参考文献：
  名称：

  Tamoto, Katsumi; Terashima, Shiro, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 11, p. 4328 - 4339

  摘要：

  DOI：

文献信息

• Novel ethynylcerium(III) reagents as efficient tools for constructing the .ALPHA.-hydroxy methyl ketone moiety of anthracyclinones.
  作者：MICHIYO SUZUKI、YOSHIKAZU KIMURA、SHIRO TERASHIMA

  DOI：10.1248/cpb.34.1531

  日期：——

  The title cerium(III) reagents (7-10) were found to react with 5, 8-dimethoxy-2-tetralone (11a) and 5, 12-dihydroxy-1, 2, 3, 4-tetrahydronaphthacene-2, 6, 11-trione (15) more efficiently than the corresponding lithium and magnesium reagents (3, 5, and 4, 6), giving the addition products (12a, 13a, and 17) in high yields. Hydration of these adducts readily afforded the α-hydroxy methyl ketones, 2-acetyl-5, 8-dimethoxy-1, 2, 3, 4-tetrahydro-2-naphthol (14a), and 2-acetyl-2, 5, 12-trihydroxy-1, 2, 3, 4-tetrahydronaphthacene-6, 11-dione (4-demethoxy-7-deoxydaunomycinone) (18), which are versatile synthetic intermediates for optically active 4-demethoxyanthracyclinones.

  标题铈(III)试剂（7-10）被发现与5, 8-二甲氧基-2-四氢萘酮（11a）和5, 12-二羟基-1, 2, 3, 4-四氢萘蒽-2, 6, 11-三酮（15）反应更有效，相比于相应的锂和镁试剂（3, 5, 和 4, 6），生成加成产物（12a, 13a, 和 17），产率较高。这些加成物的亲水化迅速提供了α-羟甲基酮，2-乙酰基-5, 8-二甲氧基-1, 2, 3, 4-四氢-2-萘酚（14a），和2-乙酰基-2, 5, 12-三羟基-1, 2, 3, 4-四氢萘蒽-6, 11-二酮（4-去甲氧基-7-脱氧道诺霉酮）（18），它们是光学活性4-去甲氧基蒽环酮的有用合成中间体。
• New strategy for the synthesis of key anthracycline precursors
  作者：John F. Honek、Michael L. Mancini、Bernard Belleau

  DOI：10.1016/s0040-4039(00)81379-9

  日期：1983.1

  A novel, practical approach to the synthesis of anthrocyclines precursor was developed. It centers on the use of the new ketimine synthon .

  开发了一种新颖，实用的蒽环素前体合成方法。它以新的酮亚胺合成素的使用为中心。
• A NOVEL SYNTHESIS OF THE α-HYDROXYKETONE MOIETY OF ANTHRACYCLINONES BY THE USE OF 2-TRIMETHYLSILYLETHYNYLCERIUM(III) REAGENTS
  作者：Michiyo Suzuki、Yoshikazu Kimura、Shiro Terashima

  DOI：10.1246/cl.1984.1543

  日期：1984.9.5

  ium(III) reagents were found to efficiently react with 1,2,3,4-tetrahydronaphthalene-2-one derivatives, giving the corresponding adducts in high yields. Hydration of the adducts readily afforded the α-hydroxy methyl ketones which are versatile synthetic intermediates of natural and unnatural anthracyclinones.

  发现 2-三甲基甲硅烷基乙炔基铈 (III) 试剂与 1,2,3,4-四氢萘-2-one 衍生物有效反应，以高产率得到相应的加合物。加合物的水合很容易得到 α-羟甲基酮，它是天然和非天然蒽环酮的通用合成中间体。
• A novel racemization mechanism for the α-hydroxy ketone moiety(C9-position) of optically active anthracyclinone derivatives
  作者：Shiro Terashima、Katsumi Tamoto

  DOI：10.1016/s0040-4039(00)81989-9

  日期：1983.1

  The facile acid-catalyzed racemization of optically active anthracyclinone derivatives ((S)(+)-1a,b) was found to proceed through the ring-expanded seven-membered α-hydroxy ketones(2 and/or 3 for (S)(+)-1a) by subjecting various plausible intermediates to the racemization condition.

  发现旋光活性蒽环酮衍生物（（S）（+）-1a，b）的轻度酸催化外消旋作用通过扩环的七元α-羟基酮（（S）（2和/或3）进行） +）-1a）通过使各种可能的中间体经历外消旋化条件。
• 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：