3,4-dihydrophenanthren-2(1H)-one | 68715-26-4

• 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: 3,4-dihydrophenanthren-2(1H)-one
• 英文别名: 2(1H)-Phenanthrenone, 3,4-dihydro-；3,4-dihydro-1H-phenanthren-2-one
• CAS: 68715-26-4
• 化学式: C₁₄H₁₂O
• 分子量: 196.249
• InChiKey: BHZRMLCGRKKPTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4-dihydrophenanthren-2(1H)-one 在 sodium ethanolate 、 sodium hydride 作用下， 以 乙醇 为溶剂， 反应 22.25h， 生成 2-Amino-11,12-dihydro-3H-1,3-diaza-chrysen-4-one
  参考文献：
  名称：

  Benzoquinazoline inhibitors of thymidylate synthase: enzyme inhibitory activity and cytotoxicity of some 3-amino- and 3-methylbenzo[f]quinazolin-1(2H)-ones

  摘要：

  The synthesis and thymidylate synthase (TS) inhibitory activity of a series of simple benzo-[f]-quinazolin-1(2H)-ones are described. Fully aromatic 3-amino compounds with compact lipophilic substituents in the 9-position were found to have I50 values as low as 20 nM on the isolated enzyme, and represent the first examples of potent, folate-based TS inhibitors that completely lack any structural feature corresponding to the (p-aminobenzoyl)glutamate moiety of the cofactor. A number of the compounds also showed moderate growth inhibitory activity against a human colon adenocarcinoma cell line (SW480), with IC50 values as low as 2 muM.

  DOI：

  10.1021/jm00068a004
• 作为产物：
  描述：

  1-(but-3-yn-1-yl)naphthalene 在 2,6-二氯吡啶N-氧化物 、 C₃₃H₅₄AuClP 、 四(3,5-二(三氟甲基)苯基)硼酸钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.5h， 以94%的产率得到3,4-dihydrophenanthren-2(1H)-one
  参考文献：
  名称：

  金催化的氧化末端炔烃：合成取代的二氢萘-2（1 H）-一和苯二酚的一种方法

  摘要：

  实现了一种简便的金催化的氧化末端炔烃，用于合成取代的二氢萘-2（1 H）-酮3和菲酚5。在温和的条件下和低的催化剂负载下，可以以高达99％的产率生成各种有用的结构和药物前体。

  DOI：

  10.1021/acs.joc.7b01244

文献信息

• [EN] SYNTHESIS OF MORPHINE AND RELATED DERIVATIVES<br/>[FR] SYNTHÈSE DE LA MORPHINE ET DE DÉRIVÉS ASSOCIÉS
  申请人：UNIV TEXAS

  公开号：WO2010132570A1

  公开（公告）日：2010-11-18

  The present invention relates to methods for the synthesis of galanthamine, morphine, intermediates, salts and derivatives thereof, wherein the starting compound is biphenyl.

  本发明涉及一种合成迷迭香碱、吗啡、中间体、盐和衍生物的方法，其中起始化合物为联苯。
• Enantioselectivity in the reduction of tricyclic hydroaromatic ketones by baker's yeast
  作者：Gabriele Fontana、Paolo Manitto、Giovanna Speranza、Simona Zanzola

  DOI：10.1016/s0957-4166(98)00111-6

  日期：1998.4

  Three benzo-2-tetralones were hydrogenated to the corresponding alcohols by non-fermenting baker's yeast. Satisfactory yields but modest enantioselectivities were observed. The prevalent enantioform of the benzo-2-tetralol was found to be in agreement with the predictive abstract model previously proposed for the enzymatic hydrogenation of aromatic ring substituted 2-tetralones.

  通过非发酵面包酵母将三种苯并-2-四氢萘酮氢化为相应的醇。令人满意的产率，但是观察到适度的对映选择性。发现苯并-2-戊醇的普遍对映体与先前提出的用于芳香环取代的2-四氢萘酮的酶促氢化的预测抽象模型相符。
• Efficient Synthesis Of Morphine And Codeine
  申请人：Magnus Philip D.

  公开号：US20100292475A1

  公开（公告）日：2010-11-18

  The present invention relates to methods for the synthesis of morphine, intermediates, salts and derivatives thereof. In preferred embodiments, the invention relates to methods for improving the efficiency and overall yield of said morphine, morphine related derivatives and intermediates thereof. In further embodiments, the invention relates to methods for improving the efficiency and overall yield of galanthamine and intermediates thereof.

  本发明涉及吗啡、中间体、盐和衍生物的合成方法。在优选实施例中，本发明涉及改善吗啡、吗啡相关衍生物和中间体的效率和总产量的方法。在进一步实施例中，本发明涉及改善迷迭香碱及其中间体的效率和总产量的方法。
• Efficient Synthesis Of Galanthamine
  申请人：Magnus Philip D.

  公开号：US20100292466A1

  公开（公告）日：2010-11-18

  The present invention relates to methods for the synthesis of galanthamine, morphine, intermediates, salts and derivatives thereof. In preferred embodiments, the invention relates to methods for improving the efficiency and overall yield of said morphine, morphine related derivatives and intermediates thereof. In further embodiments, the invention relates to methods for improving the efficiency and overall yield of galanthamine and intermediates thereof.

  本发明涉及合成迷达唑啉、吗啡、中间体、盐和衍生物的方法。在优选实施例中，本发明涉及提高吗啡、吗啡相关衍生物和中间体的效率和总产率的方法。在进一步的实施例中，本发明涉及提高迷达唑啉及其中间体的效率和总产率的方法。
• Cross-conjugated 2,5-cyclohexadienone and related synthesis methods
  申请人：Magnus Philip D.

  公开号：US20100292489A1

  公开（公告）日：2010-11-18

  The present invention relates to methods for the synthesis of galanthamine, morphine, intermediates, salts and derivatives thereof. In preferred embodiments, the invention relates to methods for improving the efficiency and overall yield of said morphine, morphine related derivatives and intermediates thereof. In further embodiments, the invention relates to methods for improving the efficiency and overall yield of galanthamine and intermediates thereof.

  本发明涉及合成无花果碱、吗啡、中间体、盐和衍生物的方法。在优选实施例中，本发明涉及改善吗啡、吗啡相关衍生物和中间体的效率和总产率的方法。在进一步的实施例中，本发明涉及改善无花果碱及其中间体的效率和总产率的方法。