(-)-(R)-7-methoxy-1,6-dimethyl-1,2,3,4-tetrahydronaphthalene | 1131235-53-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (-)-(R)-7-methoxy-1,6-dimethyl-1,2,3,4-tetrahydronaphthalene
• 英文别名: (-)-(R)-1,2,3,4-tetrahydro-7-methoxy-1,6-dimethylnaphthalene；(1R)-7-methoxy-1,6-dimethyl-1,2,3,4-tetrahydronaphthalene
• CAS: 1131235-53-4
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: WQMFIPKWRLORFF-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (-)-(R)-7-methoxy-1,6-dimethyl-1,2,3,4-tetrahydronaphthalene 在 chromium(VI) oxide 、 水 、 溶剂黄146 作用下， 以80%的产率得到(+)-(R)-6-methoxy-4,7-dimethyl-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  (+)- and (−)-Mutisianthol: First Total Synthesis, Absolute Configuration, and Antitumor Activity

  摘要：

  The first synthesis of the natural product (+)-mutisianthol was accomplished in 11 steps and in 21% overall yield from 2-methylanisole. The synthesis of its enantiomer was also performed in a similar overall yield. The absolute configuration of the sesquiterpene (+)-mutisianthol was assigned as (1S,3R). Key steps in the route are the asymmetric hydrogenation of a nonfunctionalized olefin using chiral iridium catalysts and the ring contraction of 1,2-dihydronaphthalenes using thallium(III) or iodine(III). The target molecules show moderate activity against the human tumor cell lines SF-295, HCT-8, and MDA-MB-435.

  DOI：

  10.1021/jo9000405
• 作为产物：
  描述：

  1,2-dihydro-6-methoxy-4,7-dimethylnaphthalene 在 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、10.0 MPa 条件下， 反应 3.0h， 以97%的产率得到(-)-(R)-7-methoxy-1,6-dimethyl-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  (+)- and (−)-Mutisianthol: First Total Synthesis, Absolute Configuration, and Antitumor Activity

  摘要：

  The first synthesis of the natural product (+)-mutisianthol was accomplished in 11 steps and in 21% overall yield from 2-methylanisole. The synthesis of its enantiomer was also performed in a similar overall yield. The absolute configuration of the sesquiterpene (+)-mutisianthol was assigned as (1S,3R). Key steps in the route are the asymmetric hydrogenation of a nonfunctionalized olefin using chiral iridium catalysts and the ring contraction of 1,2-dihydronaphthalenes using thallium(III) or iodine(III). The target molecules show moderate activity against the human tumor cell lines SF-295, HCT-8, and MDA-MB-435.

  DOI：

  10.1021/jo9000405

文献信息

• (+)- and (−)-Mutisianthol: First Total Synthesis, Absolute Configuration, and Antitumor Activity
  作者：Graziela G. Bianco、Helena M. C. Ferraz、Arinice M. Costa、Letícia V. Costa-Lotufo、Cláudia Pessoa、Manoel O. de Moraes、Marcus G. Schrems、Andreas Pfaltz、Luiz F. Silva

  DOI：10.1021/jo9000405

  日期：2009.3.20

  The first synthesis of the natural product (+)-mutisianthol was accomplished in 11 steps and in 21% overall yield from 2-methylanisole. The synthesis of its enantiomer was also performed in a similar overall yield. The absolute configuration of the sesquiterpene (+)-mutisianthol was assigned as (1S,3R). Key steps in the route are the asymmetric hydrogenation of a nonfunctionalized olefin using chiral iridium catalysts and the ring contraction of 1,2-dihydronaphthalenes using thallium(III) or iodine(III). The target molecules show moderate activity against the human tumor cell lines SF-295, HCT-8, and MDA-MB-435.