(3aS,6R,6aS,9aR,9bR)-9b-Hydroxy-6,9-dimethyl-3-methylene-3a,4,5,6,6a,7,9a,9b-octahydro-3H-benzo[de]chromen-2-one | 64439-86-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3aS,6R,6aS,9aR,9bR)-9b-Hydroxy-6,9-dimethyl-3-methylene-3a,4,5,6,6a,7,9a,9b-octahydro-3H-benzo[de]chromen-2-one
• 英文别名: (1R,5S,8R,9S,13R)-13-hydroxy-8,12-dimethyl-4-methylidene-2-oxatricyclo[7.3.1.05,13]tridec-11-en-3-one
• CAS: 64439-86-7
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: PTXJFFZECVHEHC-JDRMZHCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aS,6R,6aS,9aR,9bR)-9b-Hydroxy-6,9-dimethyl-3-methylene-3a,4,5,6,6a,7,9a,9b-octahydro-3H-benzo[de]chromen-2-one 在 甲醇 、 水 、 magnesium 、 cadmium(II) chloride 作用下， 反应 0.25h， 生成 (3S,3aS,6R,6aS,9aR,9bR)-9b-Hydroxy-3,6,9-trimethyl-3a,4,5,6,6a,7,9a,9b-octahydro-3H-benzo[de]chromen-2-one 、 (3R,3aS,6R,6aS,9aR,9bR)-9b-Hydroxy-3,6,9-trimethyl-3a,4,5,6,6a,7,9a,9b-octahydro-3H-benzo[de]chromen-2-one
  参考文献：
  名称：

  Selective Reduction of the Exomethylene Group of α-Methylene γ- or δ-Lactones with CdCl2–Mg–MeOH–H2O‡

  摘要：

  倍半萜类化合物中δ-亚甲基δ-或δ-内酯分子的受约束外亚甲基可以用 CdCl2âMgâMeOHâH2O 试剂体系进行选择性还原。

  DOI：

  10.1039/a803981j
• 作为产物：
  描述：

  青蒿素 B 在 氢溴酸 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以80%的产率得到(3aS,6R,6aS,9aR,9bR)-9b-Hydroxy-6,9-dimethyl-3-methylene-3a,4,5,6,6a,7,9a,9b-octahydro-3H-benzo[de]chromen-2-one
  参考文献：
  名称：

  Stereoselective reduction of arteannuin B and its chemical transformations

  摘要：

  Absolute stereochemistry of dihydroarteannuin B 5 obtained by the reduction of arteannuin B 3 with Ni2B, NaBH4 or CdCl2-Mg-MeOH-H2O has been established by 2D NMR and single crystal X-ray diffraction studies. Some experiments aimed at the synthesis of dihydrodeoxyarteannuin B [C-4, 5 double bond isomer of 11] are also discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00330-2

文献信息

• Selective Reduction of the Exomethylene Group of α-Methylene γ- or δ-Lactones with CdCl2–Mg–MeOH–H2O‡
  作者：Asish K. Bhattacharya、Dharam C. Jain、Ram P. Sharma

  DOI：10.1039/a803981j

  日期：——

  The strained exomethylene group of the α-methylene γ- or δ-lactone moiety in sesquiterpenoids can be selectively reduced with the CdCl2–Mg–MeOH–H2O reagent system.

  倍半萜类化合物中δ-亚甲基δ-或δ-内酯分子的受约束外亚甲基可以用 CdCl2âMgâMeOHâH2O 试剂体系进行选择性还原。
• Stereoselective reduction of arteannuin B and its chemical transformations
  作者：Asish K Bhattacharya、Mahesh Pal、Dharam C Jain、Bhawani S Joshi、Raja Roy、Urszula Rychlewska、Ram P Sharma

  DOI：10.1016/s0040-4020(03)00330-2

  日期：2003.4

  Absolute stereochemistry of dihydroarteannuin B 5 obtained by the reduction of arteannuin B 3 with Ni2B, NaBH4 or CdCl2-Mg-MeOH-H2O has been established by 2D NMR and single crystal X-ray diffraction studies. Some experiments aimed at the synthesis of dihydrodeoxyarteannuin B [C-4, 5 double bond isomer of 11] are also discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.