(+)-(R)-7-bromo-2-ethyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-1-one | 131863-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (+)-(R)-7-bromo-2-ethyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-1-one
• 英文别名: (2R)-7-bromo-2-ethyl-2-hydroxy-5,8-dimethoxy-3,4-dihydronaphthalen-1-one
• CAS: 131863-81-5
• 化学式: C₁₄H₁₇BrO₄
• 分子量: 329.191
• InChiKey: INZQTNGGTGYURO-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 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：

  乙酸酐 、 (+)-(R)-7-bromo-2-ethyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-1-one 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 2-acetoxy-7-bromo-2-ethyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-1-one
  参考文献：
  名称：

  Chemistry of oxaziridines. 16. A short, highly enantioselective synthesis of the AB-ring segments of .gamma.-rhodomycionone and .alpha.-citromycinone using (+)-[(8,8-dimethoxycamphoryl)sulfonyl]oxaziridine

  摘要：

  A highly efficient procedure for the preparation of rhodomycinone 1 AB synthons (-)-2a and (+)-2b in high enantiomeric purity (93-4% ee) and good yield is described. This method involves asymmetric oxidation of the lithium enolate of 2-ethyl-5,8-dimethoxy-1-tetralone (4) with (+)-[(8,8-dimethoxycamphoryl)sulfonyl]oxaziridine (5c), a new enantiomerically pure, aprotic oxidizing reagent. Lower stereoselectivities were observed with this reagent for the enantioselective oxidation of 2-substituted 1-tetralone enolates 8 lacking the 8-methoxy group.

  DOI：

  10.1021/jo00003a042
• 作为产物：
  描述：

  5,8-二甲氧基-1-四氢萘酮 在 (+)-<(3,3-dimethoxycamphoryl)sulfonyl>oxaziridine 、 溴 、 sodium hexamethyldisilazane 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 43.0h， 生成 (+)-(R)-7-bromo-2-ethyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-1-one
  参考文献：
  名称：

  Chemistry of oxaziridines. 16. A short, highly enantioselective synthesis of the AB-ring segments of .gamma.-rhodomycionone and .alpha.-citromycinone using (+)-[(8,8-dimethoxycamphoryl)sulfonyl]oxaziridine

  摘要：

  A highly efficient procedure for the preparation of rhodomycinone 1 AB synthons (-)-2a and (+)-2b in high enantiomeric purity (93-4% ee) and good yield is described. This method involves asymmetric oxidation of the lithium enolate of 2-ethyl-5,8-dimethoxy-1-tetralone (4) with (+)-[(8,8-dimethoxycamphoryl)sulfonyl]oxaziridine (5c), a new enantiomerically pure, aprotic oxidizing reagent. Lower stereoselectivities were observed with this reagent for the enantioselective oxidation of 2-substituted 1-tetralone enolates 8 lacking the 8-methoxy group.

  DOI：

  10.1021/jo00003a042

文献信息

• DAVIS, FRANKLIN A.;KUMAR, ANIL;CHEN, BANG-CHI, J. ORG. CHEM., 56,(1991) N, C. 1143-1145
  作者：DAVIS, FRANKLIN A.、KUMAR, ANIL、CHEN, BANG-CHI

  DOI：——

  日期：——
• Chemistry of oxaziridines. 16. A short, highly enantioselective synthesis of the AB-ring segments of .gamma.-rhodomycionone and .alpha.-citromycinone using (+)-[(8,8-dimethoxycamphoryl)sulfonyl]oxaziridine
  作者：Franklin A. Davis、Anil Kumar、Bang Chi Chen

  DOI：10.1021/jo00003a042

  日期：1991.2

  A highly efficient procedure for the preparation of rhodomycinone 1 AB synthons (-)-2a and (+)-2b in high enantiomeric purity (93-4% ee) and good yield is described. This method involves asymmetric oxidation of the lithium enolate of 2-ethyl-5,8-dimethoxy-1-tetralone (4) with (+)-[(8,8-dimethoxycamphoryl)sulfonyl]oxaziridine (5c), a new enantiomerically pure, aprotic oxidizing reagent. Lower stereoselectivities were observed with this reagent for the enantioselective oxidation of 2-substituted 1-tetralone enolates 8 lacking the 8-methoxy group.