7-methoxy-6-isopropyl-1,2-dihydronaphthalene | 100971-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-methoxy-6-isopropyl-1,2-dihydronaphthalene
• 英文别名: (3-isopropyl-5,6-dihydro-[2]naphthyl)-methyl ether；(3-Isopropyl-5,6-dihydro-[2]naphthyl)-methyl-aether；6-Methoxy-7-propan-2-yl-1,2-dihydronaphthalene
• CAS: 100971-64-0
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: UNWRTLSNMYBFOR-UHFFFAOYSA-N

物化性质

• 沸点：
  80 °C(Press: 0.1 Torr)
• 密度：
  0.993±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  7-methoxy-6-isopropyl-1,2-dihydronaphthalene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到(3-异丙基-[2]萘基)-甲基醚
  参考文献：
  名称：

  Compounds from Danshen. Part 4. Structure-activity relationship of miltirone, an active central benzodiazepine receptor ligand isolated from Salvia miltiorrhiza Bunge (Danshen)

  摘要：

  Twenty one o-quinonoid-type compounds and one coumarin-type compound related to miltirone (1) have been synthesized with the aim to identify the key structural elements involved in miltirone's interaction with the central benzodiazepine receptor. On the basis of their inhibition of [H-3]flunitrazepam binding to bovine cerebral cortex membranes, it is apparent that ring A of miltirone is essential for affinity. Although increasing the size of ring A from six-membered to seven- and eight-membered is well-tolerated, the introduction of polar hydroxyl groups greatly reduces binding affinity. The presence of 1,1-dimethyl groups on ring A is, however, not essential. On the other hand, the isopropyl group on ring C appears to be critical for binding as its removal decreases affinity by more than 30-fold. It can, however, be replaced with a methyl group with minimal reduction in affinity. Finally, linking ring A and B with a -CH2CH2- bridge results in analogue 89, which is 6 times more potent than miltirone at the central benzodiazepine receptor (IC50 = 0.05-mu-M).

  DOI：

  10.1021/jm00109a022
• 作为产物：
  描述：

  6-isopropyl-7-methoxy-1-tetralone 在 对甲苯磺酸 、 2,4-戊二醇 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以90%的产率得到7-methoxy-6-isopropyl-1,2-dihydronaphthalene
  参考文献：
  名称：

  6-异丙基-7-甲氧基-1-四氢萘酮和6-异丙基-7-甲氧基-2-四氢萘酮的一锅法合成

  摘要：

  6-异丙基-7-甲氧基-1-四氢萘酮1 (2) 和6-异丙基-7-甲氧基-2-四氢萘酮2 (4) 已被声称是合成与二萜米替龙 (5) 相关的天然产物的潜在中间体和鼠尾草酸 (6)，分别。Miltirone，一种丹参酮（邻醌二萜），从 S. miltiorrhiza3 和其他物种 4 中分离出来，之前已经合成 5,6 并且对许多培养的肿瘤细胞系具有细胞毒性7。鼠尾草酸，一种天然存在的儿茶酚型多酚二萜，从迷迭香（迷迭香）叶中获得 8，之前也已合成。9,10 鼠尾草酸已知具有强大的抗氧化活性以及抗癌和抗病毒特性。11-13 1990 年，据报道，由 2-异丙基苯酚四步合成四氢萘酮 2，总产率为 24%1，而由 2,7-二甲氧基萘制备四氢萘酮 4 分六步完成，总产率为 39%2。四氢萘酮 2 和 4 的高产方法将有助于扩大制备前面提到的和相关的天然产物。此外，以高产率合成这两种四氢萘酮将有利于 5

  DOI：

  10.1080/00304948.2014.903146

文献信息

• Synthesis of miltirone analogues as inhibitors of Cdc25 phosphatases
  作者：Weigang Huang、Jingya Li、Wei Zhang、Yueyang Zhou、Chuanming Xie、Yu Luo、Yunfei Li、Jingli Wang、Jia Li、Wei Lu

  DOI：10.1016/j.bmcl.2005.12.080

  日期：2006.4

  Miltirone analogues were synthesized and evaluated for inhibitory activity against Cdc25 and PTP1B. Most of the compounds demonstrated potent Cdc25 inhibitory activity, and several exhibited higher selectivity for Cdc25 than for PTP1B. In a cytotoxic assay, most of the compounds displayed cytotoxicity against the tumor cell lines A549 and HCT-116, producing IC50 values in the micromolar range. (C) 2006 Elsevier Ltd. All rights reserved.
• Sengupta et al., Journal of the Indian Chemical Society, 1959, vol. 36, p. 659,665
  作者：Sengupta et al.

  DOI：——

  日期：——
• CHANG, HSON MOU;CHUI, KUK YING;TAN, FAN WAH LAU;YANG, YUN;ZHONG, ZENG PEI+, J. MED. CHEM., 34,(1991) N, C. 1675-1692
  作者：CHANG, HSON MOU、CHUI, KUK YING、TAN, FAN WAH LAU、YANG, YUN、ZHONG, ZENG PEI+

  DOI：——

  日期：——