2-ethyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-1-one | 93834-66-3

• 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-ethyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-1-one
• 英文别名: 2-ethyl-5,8-dimethoxy-3,4-dihydro-2H-naphthalen-1-one；2-Aethyl-5,8-dimethoxy-3,4-dihydro-2H-naphthalin-1-on；2-Ethyl-5,8-dimethoxy-3,4-dihydronaphthalen-1(2H)-one；2-ethyl-5,8-dimethoxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 93834-66-3
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: HPCAVUQOEROCKE-UHFFFAOYSA-N

物化性质

• 熔点：
  56.5-57.0 °C
• 沸点：
  381.4±42.0 °C(Predicted)
• 密度：
  1.073±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-ethyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-1-one 在 (+)-<(3,3-dimethoxycamphoryl)sulfonyl>oxaziridine 、 溴 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 30.5h， 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
• 作为产物：
  描述：

  2-ethyl-4-(2'5'-dimethoxyphenyl) butyric acid 在 五氯化磷 、 四氯化锡 作用下， 生成 2-ethyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-1-one
  参考文献：
  名称：

  Synthesen in der Naphthalinreihe: Methoxylierte Tetralone und Naphthole

  摘要：

  DOI：

  10.1007/bf00900430

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.
• Synthesen in der Naphthalinreihe: Methoxylierte Tetralone und Naphthole
  作者：O. Brunner、P. Hanke

  DOI：10.1007/bf00900430

  日期：——