1,2,3,4-Tetrahydro-1,1-dimethyl-6-methoxyphenanthrene | 126979-87-1

• 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: 1,2,3,4-Tetrahydro-1,1-dimethyl-6-methoxyphenanthrene
• 英文别名: 1,2,3,4-tetrahydro-6-methoxy-1,1-dimethylphenanthrene；6-Methoxy-1,1-dimethyl-1,2,3,4-tetrahydrophenanthrene；1,2,3,4-Tetrahydro-6-methoxy-1,1-dimethyl-phenanthren；6-methoxy-1,1-dimethyl-3,4-dihydro-2H-phenanthrene
• CAS: 126979-87-1
• 化学式: C₁₇H₂₀O
• 分子量: 240.345
• InChiKey: AGBSKZPMRBIRCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  1,2,3,4-Tetrahydro-1,1-dimethyl-6-methoxyphenanthrene 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 、 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 17.0h， 生成 1,2,3,4-Tetrahydro-1,1-dimethyl-6-methoxyphenanthrene
  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

• Intramolecular Diels–Alder additions to 2-benzopyran-3-ones; endo-selective additions and some reactions of the adducts
  作者：David W. Jones、Firstborn Matthew Nongrum

  DOI：10.1039/p19960000705

  日期：——

  system e.g. 18a (n= 3 or 4), the 2-benzopyran-3-ones 10a, 10b and 10c undergo endo-selective intramolecular Diels–Alder addition of the connecting chain to give cis-BC fused ring systems of type 13. The adduct 13b is converted into the ester 21 with methanolic HCl and into the ketol 36 by LiAlH4 reduction followed by oxidation (MnO2). The ketone 31 is prepared from 21 by epoxidation followed by BF3·Et2O-catalysed

  与在二烯体系的末端之间缺少桥键的邻喹啉甲烷（例如18a（n = 3或4））不同，2-苯并吡喃-3-酮10a，10b和10c经历了内链选择性分子内Diels-Alder加成连接链的过程得到13型的顺式-BC稠合环系统。加合物13b用HCl的甲醇溶液转化成酯21，并通过LiAlH 4还原然后氧化（MnO 2）转化成酮醇36 。酮31由21进行环氧化，然后由BF 3 ·Et 2 O催化重排制备；使用NaOMe-CD 3 OD时，它无法顺式-反式异构化，并且由于C-6质子的酸度过高，未能在C-8处引入氘。由21获得的顺式-二氢萘26得到带有KOBu t-（CD 3）2 SO的顺式-27，在这种情况下显示出更大的顺式稠合环体系的热力学稳定性。
• Structure elucidation and total synthesis of new tanshinones isolated from Salvia miltiorrhiza Bunge (Danshen)
  作者：Hson Mou Chang、Kwok Ping Cheng、Tai Francis Choang、Hak Fun Chow、Kuk Ying Chui、Po Ming Hon、Fan Wah Lau Tan、Yun Yang、Zeng Pei Zhong

  DOI：10.1021/jo00298a029

  日期：1990.5
• 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).
• Ghosh, Sukumar; Banik, Bimal K.; Ghatak, Usha Ranjan, Journal of the Chemical Society. Perkin transactions I, 1991, # 12, p. 3195 - 3198
  作者：Ghosh, Sukumar、Banik, Bimal K.、Ghatak, Usha Ranjan

  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：——