1,1-dimethyl-1,2,3,4-tetrahydrophenanthren-6-ol | 133130-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1,1-dimethyl-1,2,3,4-tetrahydrophenanthren-6-ol
• 英文别名: 1,2,3,4-Tetrahydro-6-hydroxy-1,1-dimethyl-phenanthren；8,8-Dimethyl-5,6,7,8-tetrahydrophenanthren-3-OL；8,8-dimethyl-6,7-dihydro-5H-phenanthren-3-ol
• CAS: 133130-79-7
• 化学式: C₁₆H₁₈O
• 分子量: 226.318
• InChiKey: NZPHFMVNAUUXKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,1-dimethyl-1,2,3,4-tetrahydrophenanthren-6-ol 生成 5,6,7,8-Tetrahydro-3-hydroxy-8,8-dimethyl-phenanthrachinon-(1,4)
  参考文献：
  名称：

  天然存在的醌。第十一部分。丹参酮

  摘要：

  通过合成建立了来自丹参丹参的色素丹参酮I，丹参酮IIA和隐丹参酮的结构。关键步骤是通过与β-氯丙酰过氧化物反应，将2-羟基-1,4-醌转化为二氢呋喃-邻-醌。将8-甲基-3-菲咯啉转化为3-羟基-8-甲基-1,4-菲蒽醌，得到2,3,4,5-四氢-3,9-二甲基菲[1,2- b ]-呋喃-通过与β-氯-α-甲基丙酰过氧化物反应来形成4,5-二酮。随后用二氯二氰基苯并苯醌脱氢得到丹参酮l（4,5-二氢-3,9-二甲基菲[1,2- b]呋喃-4,5-二酮）。通过相同的途径，将5,6,7,8-四氢-8,8-二甲基-3-菲酚转化为外消旋隐丹参酮（2,3,4,5,6,7,8,9-八氢-3,9 ，9-三甲基菲蒽[1,2- b ]呋喃-4,5-二酮）经脱氢得到丹参酮IIA。由光谱数据推断丹参酮IIB为4,5,6,7,8,9-六氢-9-羟甲基-3,9-二甲基菲蒽[1,2 - b ]呋喃-4,5-二酮。

  DOI：

  10.1039/j39680000048
• 作为产物：
  描述：

  3-(4-甲氧基苯甲酰基)丙酸 在 钯 氢氧化钾 、 磷酸 、 三氟化硼乙醚 、 phosphorus pentoxide 、 三溴化硼 、 一水合肼 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 二乙二醇 为溶剂， 反应 20.0h， 生成 1,1-dimethyl-1,2,3,4-tetrahydrophenanthren-6-ol
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Tanshinone Analogues

  摘要：

  DOI：

  10.1023/b:conc.0000003428.26731.7f

文献信息

• Compounds from Danshen. Part 4. Structure-activity relationship of miltirone, an active central benzodiazepine receptor ligand isolated from Salvia miltiorrhiza Bunge (Danshen)
  作者：Hson Mou Chang、Kuk Ying Chui、Fan Wah Lau Tan、Yun Yang、Zeng Pei Zhong、Chi Ming Lee、Hing Leung Sham、Henry N. C. Wong

  DOI：10.1021/jm00109a022

  日期：1991.5

  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).
• 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：——
• Synthesis and Antitumor Activity of Tanshinone Analogues
  作者：Haji Akber Aisa、Wei Lu、Junchao Cai

  DOI：10.1023/b:conc.0000003428.26731.7f

  日期：2003.7
• Naturally occurring quinones. Part XI. The tanshinones
  作者：A. C. Baillie、R. H. Thomson

  DOI：10.1039/j39680000048

  日期：——

  dichlorodicyanobenzoquinone yielded tanshinone l (4,5-dihydro-3,9-dimethylphenanthra[1,2-b]furan-4,5-dione). By the same route 5,6,7,8-tetrahydro-8,8-dimethyl-3-phenanthrol was converted into racemic cryptotanshinone (2,3,4,5,6,7,8,9-octahydro-3,9,9-trimethylphenanthra[1,2-b]furan-4,5-dione) which gave tanshinone IIA on dehydrogenation. It is deduced from spectroscopic data that tanshinone IIB is 4,5,6,7,8,9-he

  通过合成建立了来自丹参丹参的色素丹参酮I，丹参酮IIA和隐丹参酮的结构。关键步骤是通过与β-氯丙酰过氧化物反应，将2-羟基-1,4-醌转化为二氢呋喃-邻-醌。将8-甲基-3-菲咯啉转化为3-羟基-8-甲基-1,4-菲蒽醌，得到2,3,4,5-四氢-3,9-二甲基菲[1,2- b ]-呋喃-通过与β-氯-α-甲基丙酰过氧化物反应来形成4,5-二酮。随后用二氯二氰基苯并苯醌脱氢得到丹参酮l（4,5-二氢-3,9-二甲基菲[1,2- b]呋喃-4,5-二酮）。通过相同的途径，将5,6,7,8-四氢-8,8-二甲基-3-菲酚转化为外消旋隐丹参酮（2,3,4,5,6,7,8,9-八氢-3,9 ，9-三甲基菲蒽[1,2- b ]呋喃-4,5-二酮）经脱氢得到丹参酮IIA。由光谱数据推断丹参酮IIB为4,5,6,7,8,9-六氢-9-羟甲基-3,9-二甲基菲蒽[1,2 - b ]呋喃-4,5-二酮。