7,8-didehydro-4-(4-fluorobenzyloxy)-3,7-dimethoxy-17-methylmorphinan-6-one | 1335301-51-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: 7,8-didehydro-4-(4-fluorobenzyloxy)-3,7-dimethoxy-17-methylmorphinan-6-one
• 英文别名: (1R,9S,10S)-3-[(4-fluorophenyl)methoxy]-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one
• CAS: 1335301-51-3
• 化学式: C₂₆H₂₈FNO₄
• 分子量: 437.511
• InChiKey: YKMCDRJVHXKYMH-BVFVYWQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7,8-didehydro-4-(4-fluorobenzyloxy)-3,7-dimethoxy-17-methylmorphinan-6-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.42h， 以99%的产率得到
  参考文献：
  名称：

  Highly Stereoselective Synthesis of Functionalised Sinomenine Derivatives by Reducing the C-6 (Ring C)

  摘要：

  C-4（环 A）上的西诺明醚衍生物被 C-6（环 C）上的 LiAlH4 还原，以高度的立体选择性提供相应的羟基衍生物。所需的产物产量极高，并通过 1H NMR、13C NMR、MS 光谱、元素分析和 X 射线衍射进行了全面表征。温和的反应条件、易于获得的 sinomenine 醚衍生物、简单的操作和高立体选择性使该反应极具吸引力。

  DOI：

  10.3184/174751914x14176845374506
• 作为产物：
  描述：

  青藤碱 在 sodium hydroxide 作用下， 以 乙腈 为溶剂， 反应 7.0h， 生成 7,8-didehydro-4-(4-fluorobenzyloxy)-3,7-dimethoxy-17-methylmorphinan-6-one
  参考文献：
  名称：

  Design, synthesis and molecular docking studies of sinomenine derivatives

  摘要：

  In order to search for drugs with excellent anti-inflammatory activities, a series of novel sinomenine derivatives were designed, synthesized, and evaluated for their inhibition activities against NF-kappa B activation induced by lipopolysaccharide (LPS). Compared with the natural parent sinomenine, compounds 2a-w showed higher activity, while compounds 1a-o showed similar activity against NF-kappa B. Moreover, a molecular model for the binding between compound 2v and the active site of p50 was provided on the basis of the computational docking results. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.087

文献信息

• Design, synthesis and molecular docking studies of sinomenine derivatives
  作者：Xiaoyun Chai、Zhongjun Guan、Shichong Yu、Qingjie Zhao、Honggang Hu、Yan Zou、Xia Tao、Qiuye Wu

  DOI：10.1016/j.bmcl.2012.07.087

  日期：2012.9

  In order to search for drugs with excellent anti-inflammatory activities, a series of novel sinomenine derivatives were designed, synthesized, and evaluated for their inhibition activities against NF-kappa B activation induced by lipopolysaccharide (LPS). Compared with the natural parent sinomenine, compounds 2a-w showed higher activity, while compounds 1a-o showed similar activity against NF-kappa B. Moreover, a molecular model for the binding between compound 2v and the active site of p50 was provided on the basis of the computational docking results. (C) 2012 Elsevier Ltd. All rights reserved.
• Highly Stereoselective Synthesis of Functionalised Sinomenine Derivatives by Reducing the C-6 (Ring C)
  作者：Xingliang Zheng、Weihua Zhu、Liqiong Han、Kecui Zhang、Tong Pan

  DOI：10.3184/174751914x14176845374506

  日期：2014.12

  Sinomenine ether derivatives at C-4 (ring A) were reduced by LiAlH₄ at the C-6 (ring C) to provide the corresponding hydroxyl derivatives with highly stereoselectivity. The desired products were obtained in excellent yields and fully characterised by ¹H NMR, ¹³C NMR, MS spectra, elemental analysis and X-ray diffraction. The mild reaction conditions, readily available sinomenine ether derivatives, simple operation and high stereoselectivity make such a reaction highly attractive.

  C-4（环 A）上的西诺明醚衍生物被 C-6（环 C）上的 LiAlH4 还原，以高度的立体选择性提供相应的羟基衍生物。所需的产物产量极高，并通过 1H NMR、13C NMR、MS 光谱、元素分析和 X 射线衍射进行了全面表征。温和的反应条件、易于获得的 sinomenine 醚衍生物、简单的操作和高立体选择性使该反应极具吸引力。