1,6-dimethyl-7-methoxy-1,2-dihyronaphthalene | 606146-47-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,6-dimethyl-7-methoxy-1,2-dihyronaphthalene
• 英文别名: 1,2-dihydro-7-methoxy-1,6-dimethylnaphthalene；7-Methoxy-1,6-dimethyl-1,2-dihydronaphthalene
• CAS: 606146-47-8
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: ZMJQOLDZUQAVBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  1,6-dimethyl-7-methoxy-1,2-dihyronaphthalene 在 thallium(III) nitrate trihydrate 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以89%的产率得到5-methoxy-3,6-dimethyl-indan-1-carbaldehyde
  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：

  (±)-methoxy-4,7-dimethyl-3,4-dihydronaphthalen-1(2H)-one 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 2.5h， 生成 1,6-dimethyl-7-methoxy-1,2-dihyronaphthalene
  参考文献：
  名称：

  倍半萜（±）-异扁桃醇的非对映选择性全合成

  摘要：

  从容易获得的2-甲基苯甲醚以十二个步骤完成了酚倍半萜烯泛醇的全合成。所需的反式-1,3-二取代的茚满中间体是通过非对映选择性的（（III）介导的1-甲基-1，2-二氢萘衍生物的环收缩而获得的。

  DOI：

  10.1016/s0040-4020(03)00974-8

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.
• A diastereoselective total synthesis of the sesquiterpene (±)-mutisianthol
  作者：Helena M.C Ferraz、Andrea M Aguilar、Luiz F Silva

  DOI：10.1016/s0040-4020(03)00974-8

  日期：2003.7

  The total synthesis of the phenolic sesquiterpene mutisianthol has been accomplished in 12 steps from the readily available 2-methylanisole. The required trans-1,3-disubstituted indan intermediate was obtained through a diastereoselective thallium(III) mediated ring contraction of a 1-methyl-1,2-dihydronaphthalene derivative.

  从容易获得的2-甲基苯甲醚以十二个步骤完成了酚倍半萜烯泛醇的全合成。所需的反式-1,3-二取代的茚满中间体是通过非对映选择性的（（III）介导的1-甲基-1，2-二氢萘衍生物的环收缩而获得的。