5,6,7,8-tetrahydro-3-phenanthrenol | 133130-77-5

• 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: 5,6,7,8-tetrahydro-3-phenanthrenol
• 英文别名: 5,6,7,8-tetrahydrophenanthren-3-ol
• CAS: 133130-77-5
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: HJZMTEBQODMGLW-UHFFFAOYSA-N

物化性质

• 沸点：
  386.3±11.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  5,6,7,8-tetrahydro-3-phenanthrenol 在 potassium dihydrogenphosphate 、 potassium nitrososulfonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以20%的产率得到5,6,7,8-tetrahydrophenanthrene-3,4-dione
  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-methoxy-1,2,3,4-tetrahydrophenanthrene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到5,6,7,8-tetrahydro-3-phenanthrenol
  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

文献信息

• Facile synthesis of 1,2-dione-containing abietane analogues for the generation of human carboxylesterase inhibitors
  作者：Randall J. Binder、M. Jason Hatfield、Liying Chi、Philip M. Potter

  DOI：10.1016/j.ejmech.2018.02.052

  日期：2018.4

  the synthesis of such compounds is complex. Here we describe a novel method for the generation of 1,2-dione containing diterpenoids using a unified approach, by which boronic acids are joined to vinyl bromo-cyclohexene derivatives via Suzuki coupling, followed by electrocyclization and oxidation to the o-phenanthroquinones. This has allowed the construction of a panel of miltirone analogues containing

  最近，基于丹参酮已经鉴定出一系列选择性的人羧酸酯酶抑制剂，其具有1，2-二酮基团的生物活性分子作为萘醌核心的一部分。不幸的是，这类化合物的合成很复杂。在这里，我们描述了一种使用统一方法生成含1,2-二酮的二萜类化合物的新方法，该方法将硼酸通过Suzuki偶联与乙烯基溴-环己烯衍生物连接，然后进行电环化并氧化成邻位-菲醌。这允许构建一组含有一系列取代基（甲基，异丙基，氟，甲氧基）的米替隆类似物，这些取代基已用于与两种人羧酸酯酶同工型发展初步的SAR。因此，我们已经合成这些酶（K的高度有效的抑制剂我 <15纳米），其保持所述芯丹参酮支架。因此，我们开发了一种简便易行且可重现的方法，用于合成abetanene类似物，从而产生了一系列米替农衍生物，这些衍生物将是评估羧酸酯酶生物学的有用工具化合物。
• The synthesis of carnosol derivatives
  作者：Andreas Luxenburger

  DOI：10.1016/s0040-4020(03)00412-5

  日期：2003.4

  development of an efficient and flexible synthetic strategy towards the synthesis of carnosol type derivatives. The strategy involves the construction of the required trans-decalin structure with a carboxylic functionality in the angular position as well as the elaboration of the lactone ring to afford the tetracyclic core structure of the natural compound 1.

  在本文中，我们报告了一种高效，灵活的合成策略，用于合成鼠尾草酚型衍生物。该策略涉及在角位置上具有羧基官能团的所需反式-十氢萘结构的构建以及内酯环的精制以提供天然化合物1的四环核心结构。
• 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：——