(2R)-methyl 1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxy-naphthalene-2-carboxylate | 70526-26-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2R)-methyl 1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxy-naphthalene-2-carboxylate
• 英文别名: (R)-(-)-Methyl 2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthoate；(R)(-)-Methyl 5,8-dimethoxy-2-hydroxy-1,2,3,4-tetrahydro-2-naphthoate；methyl (2R)-2-hydroxy-5,8-dimethoxy-3,4-dihydro-1H-naphthalene-2-carboxylate
• CAS: 70526-26-0
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: XSVBEFALLXMURC-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R)-methyl 1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxy-naphthalene-2-carboxylate 在 aluminum amalgam 、 dimsyl sodium 作用下， 生成 抗癌药中间体
  参考文献：
  名称：

  （R）-（-）-2-乙酰基-5,8-二甲氧基-1,2,3,4-四氢-2-萘酚的高度对映选择性合成。蒽环素合成中的关键中间体

  摘要：

  AB-Synthon（R）-（-）- 5是蒽环素3和4的不对称合成中的关键中间体，其总产率为35％，ee≥95 ％。关键步骤涉及使用N-磺酰基恶唑烷（-）- 6c对7的烯醇钾进行羟化反应。

  DOI：

  10.1016/s0040-4039(00)92107-5
• 作为产物：
  描述：

  Methyl 5,8-dimethoxy-3,4-dihydronaphthalene-2-carboxylate 在 三乙基硅烷 、 四氧化锇 、 chiral diamine 、 sodium hydrogensulfite 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.33h， 生成 (2R)-methyl 1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxy-naphthalene-2-carboxylate
  参考文献：
  名称：

  Short-step asymmetric syntheses of anthracycline antibiotics via enantioselective dihydroxylation by osmium tetroxide with a chiral diamine

  摘要：

  Short-step asymmetric syntheses of (+)-7-dehydroxy-4-demethoxydaunornycinone 4 and (-)-9-deacetyl-1-7-dehydroxy-4-demethoxy-9-hydroxymethyldaunomycinone 5 were accomplished via enantioselective dihydroxylation by osmium tetroxide with chiral diamine 13.

  DOI：

  10.1016/s0040-4020(01)80235-0

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：
• AN IMPROVED ASYMMETRIC SYNTHESIS OF (<i>R</i>)-(−)-2-ACETYL-5,8-DIMETHOXY-1,2,3,4-TETRAHYDRO-2-NAPHTHOL. A VERSATILE KEY SYNTHETIC INTERMEDIATE OF OPTICALLY ACTIVE ANTHRACYCLINONES
  作者：Michiyo Suzuki、Yoshikazu Kimura、Shiro Terashima

  DOI：10.1246/cl.1985.367

  日期：1985.3.5

  The bromolactonization of the (−)-acetals prepared from readily available 2-acetyl-5,8-dimethoxy-3,4-dihydronaphthalene and (1R,2R)-(+)-tartaric acid diamide derivatives was found to proceed highly diastereoselectively, giving the seven-membered bromolactones. The bromolactones could be effectively converted to the title compound, >95%ee, in one-pot reaction.

  发现由易得的 2-乙酰基-5,8-二甲氧基-3,4-二氢萘和 (1R,2R)-(+)-酒石酸二酰胺衍生物制备的 (-)-缩醛的溴内酯化反应具有高度非对映选择性，给出七元溴内酯。溴内酯可以在一锅反应中有效地转化为标题化合物，> 95%ee。
• Enantioface differentiation in cis dihydroxylation of carbon-carbon double bonds by osmium tetroxide using a chiral diamine with D2 symmetry
  作者：Kiyoshi Tomioka、Makoto Nakajima、Kenji Koga

  DOI：10.1021/ja00254a067

  日期：1987.9
• Asymmetric Synthesis of the AB Ring Segments of Daunomycin and 4-Demethoxydaunomycin
  作者：Franklin A. Davis、Charles Clark、Anil Kumar、Bang-Chi Chen

  DOI：10.1021/jo00084a042

  日期：1994.3

  Asymmetric hydroxylation of the potassium enolate of beta-keto ester 14, with (camphorsulfonyl)-oxaziridine (-)-7c [tetrahydro-9,9-dimethyl-8,8-dimethorry-4H-4a,7-methanooxazirino[3,2-i][2,1]-benzisothiazole 3,3-dioxide] affords alpha-hydroxy beta-keto ester (R)-(+)-15 in >95% ee. The high ee's are attributed to the fact that this enolate probably exists in one geometric form as a consequence of intramolecular chelation. Reduction of the ketone in 15 with triethylsilane and conversion of the ester group into the methyl ketone results in a highly efficient synthesis of the AB ring building block (R)-(-)-2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydro-2-napthol (3b), a key intermediate in the asymmetric synthesis of the antitumor agent 4-demethoxydaunomycin (1c). Selective deprotection of the 8-methoxy group in 3b with BBr3 gives 3a, important in the enantioselective synthesis of the clinically useful antitumor agent adriamycin (1b). Attempts to prepare 3a and 3b more directly by asymmetric hydroxylation of the enolates of methyl 5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthoate (9) or the 8-benzyloxy derivative of 16 resulted in low ee's, attributable to the formation of E/Z enolate mixtures and increased steric congestion in the transition state for hydroxylation.
• Jew,S.-S. et al., Chemical and pharmaceutical bulletin, 1979, vol. 27, # 10, p. 2351 - 2362
  作者：Jew,S.-S. et al.

  DOI：——

  日期：——