(-)-(S)-1,2,3,4-tetrahydro-1-oxonaphthalen-2-yl acetate | 197140-92-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (-)-(S)-1,2,3,4-tetrahydro-1-oxonaphthalen-2-yl acetate
• 英文别名: (S)-2-acetoxy-3,4-dihydronaphthalen-1(2H)-one；(-)-(S)-2-acetoxy-α-tetralone；[(2S)-1-oxo-3,4-dihydro-2H-naphthalen-2-yl] acetate
• CAS: 197140-92-4
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: HEEOOTRAUNNUMS-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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：

  (-)-(S)-1,2,3,4-tetrahydro-1-oxonaphthalen-2-yl acetate 在 水 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲醇 为溶剂， 反应 40.0h， 以82%的产率得到2-hydroxy-1-tetralone
  参考文献：
  名称：

  Scandium trifluoromethanesulfonate-catalyzed mild, efficient, and selective cleavage of acetates bearing a coordinative group

  摘要：

  Scandium trifluoromethanesulfonate is a useful Lewis acid catalyst for cleavage of acetates containing coordinative groups adjacent to the acetyl carbonyl. The reaction proceeds under weak acidic conditions at room temperature. Racemizable alpha-keto acyloxy compounds are deacetylated without racemization. Selective mono-deacetylation at the 10-position of paclitaxel has been achieved. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00003-9
• 作为产物：
  描述：

  2-acetoxy-3,4-dihydronaphthalen-1(2H)-one 生成 (-)-(S)-1,2,3,4-tetrahydro-1-oxonaphthalen-2-yl acetate
  参考文献：
  名称：

  具有衍生自（1 R，2 S）-顺式-1,2,3,4-四氢萘-1,2-二醇的手性亚基的高手性酚醛冠醚的制备：与中性胺络合的温度依赖性对映选择性

  摘要：

  含有衍生自（1 R，2 S）-顺式-1,2,3,4-四氢萘-1,2-二醇的手性亚基的冠醚（S，R，R，S）-1和带有内部环状OH基和对位的2,4-二硝基苯基偶氮基已经以对映体纯的形式制备。通过紫外可见光谱法测定了在各种温度下与手性胺的配合物的缔合常数，并计算了配合物形成的热力学参数。

  DOI：

  10.1016/s0957-4166(97)00282-6

文献信息

• Synthesis of chiral acetoxy lactones via the Baeyer–Villiger oxidation of cyclic aromatic acetoxy ketones
  作者：Ayhan S. Demir、Asuman Aybey

  DOI：10.1016/j.tet.2008.09.035

  日期：2008.12

  kinetic resolution of acetoxy ketones furnished both of the enantiomers of α-acetoxy ketones in good chemical and optical yields. The Baeyer–Villiger oxidation of α-acetoxy ketones with m-CPBA, CF3SO3H, and CH2Cl2, at rt gives the corresponding lactones without racemization. The acetoxy ketone moiety migrates selectively in order to form lactones. The mild hydrolysis of lactones affords phenolic α-hydroxycarboxylic

  通过使用Mn（OAc）3进行茚满酮和四氢萘酮的α-乙酰氧基化反应，然后酶催化乙酰氧基酮的动力学拆分，以良好的化学和光学收率提供了α-乙酰氧基酮的两种对映体。在室温下，使用m -CPBA，CF 3 SO 3 H和CH 2 Cl 2进行α-乙酰氧基酮的BAeyer-Villiger氧化，得到相应的内酯，而没有消旋化。乙酰氧基酮部分选择性迁移以形成内酯。内酯的温和水解得到酚类α-羟基羧酸衍生物。
• Scandium Trifluoromethanesulfonate-Catalyzed Cleavage of Esters Bearing a Coordinative Group at a Vicinal Position
  作者：Hiroshi Kajiro、Shuichi Mitamura、Atsunori Mori、Tamejiro Hiyama

  DOI：10.1246/bcsj.72.1553

  日期：1999.7

  Scandium trifluoromethanesulfonate is found to be a Lewis acid catalyst for selective cleavage of esters containing a coordinative group adjacent to an ester moiety. The reaction proceeds under weak acidic conditions at room temperature; the catalyst can be recovered and reused. Even α-acyloxy ketones are deacetylated without racemization. Selective monodeacetylation at C-10 of paclitaxel has been achieved.

  研究发现，三氟甲磺酸钪是一种路易斯酸催化剂，可选择性地裂解含有邻近酯分子的配位基团的酯。反应在室温下的弱酸性条件下进行；催化剂可以回收和重复使用。即使是 α-乙酰氧基酮也能脱乙酰化而不发生外消旋化。在紫杉醇的 C-10 处实现了选择性单去乙酰化。
• Synthesis and Rhizopus oryzae mediated enantioselective hydrolysis of α-acetoxy aryl alkyl ketones
  作者：Ayhan S Demir、Haluk Hamamci、Cihangir Tanyeli、Idris M Akhmedov、Fatos Doganel

  DOI：10.1016/s0957-4166(98)00165-7

  日期：1998.5

  Mn(OAc)(3) oxidation of aromatic ketones afforded the alpha-acetoxy ketones in good yield. Selective hydrolysis of the acetoxy ketones by the fungus Rhizopus oryzae yields (R)-hydroxy ketones in high enantiomeric excess. (C) 1998 Elsevier Science Ltd. All rights reserved.
• 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.
• Kinetic resolution of racemic α-hydroxy ketones by lipase-catalyzed irreversible transesterification
  作者：Waldemar Adam、María Teresa Díaz、Rainer T. Fell、Chantu R. Saha-Möller

  DOI：10.1016/0957-4166(96)00272-8

  日期：1996.8

  Asymmetric acetylation of racemic a-hydroxy ketones with isopropenyl acetate catalyzed by lipases afforded the optically active keto alcohols and acetates in high enantiomeric excess (up to 99%); an enzymatic kinetic resolution which may be performed on preparative scale. Copyright (C) 1996 Elsevier Science Ltd