1,2,3,4-四氢-6-甲氧基-7-异丙基菲-1-酮 | 93903-00-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 1,2,3,4-四氢-6-甲氧基-7-异丙基菲-1-酮
• 英文名称: 1,2,3,4-Tetrahydro-6-methoxy-7-isopropylphenanthren-1-one
• 英文别名: 1-Oxo-6-methoxy-7-isopropyl-1,2,3,4-tetrahydro-phenanthren；1,2,3,4-Tetrahydro-7-isopropyl-6-methoxy-1-oxo-phenanthren；6-methoxy-7-propan-2-yl-3,4-dihydro-2H-phenanthren-1-one
• CAS: 93903-00-5
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: SHKPGDODVCELMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,3,4-四氢-6-甲氧基-7-异丙基菲-1-酮 在 吡啶盐酸盐 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 23.0h， 生成 3,4-dihydro-6-(benzyloxy)-7-isopropylphenanthren-1(2H)-one
  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：

  2-异丙基苯甲醚 在 钯 盐酸 、 氢氧化钾 、 三氯化铝 、 PPA 、 磷酸 、 phosphorus pentoxide 、 mercury dichloride 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 硝基苯 、 甲苯 为溶剂， 反应 29.83h， 生成 1,2,3,4-四氢-6-甲氧基-7-异丙基菲-1-酮
  参考文献：
  名称：

  Structure elucidation and total synthesis of new tanshinones isolated from Salvia miltiorrhiza Bunge (Danshen)

  摘要：

  DOI：

  10.1021/jo00298a029

文献信息

• 821. Synthetical studies in the diterpene series. Part II. Synthesis of (±)-sugiyl methyl ether and related compounds
  作者：D. Nasipuri、Maya Guha

  DOI：10.1039/jr9620004248

  日期：——
• CHANG, HSON MOU;CHENG, KWOK PING;CHOANG, TAI FRANCIS;CHOW, HAK FUN;CHUI, +, J. ORG. CHEM., 55,(1990) N1, C. 3537-3543
  作者：CHANG, HSON MOU、CHENG, KWOK PING、CHOANG, TAI FRANCIS、CHOW, HAK FUN、CHUI, +

  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：——