Methyl 6-methoxy-1,1-dimethyl-3,9-dioxo-2,4-dihydrophenanthrene-4a-carboxylate | 825638-60-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Methyl 6-methoxy-1,1-dimethyl-3,9-dioxo-2,4-dihydrophenanthrene-4a-carboxylate
• CAS: 825638-60-6
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: WPFPKGHIULAWEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 6-methoxy-1,1-dimethyl-3,9-dioxo-2,4-dihydrophenanthrene-4a-carboxylate 在 palladium on activated charcoal 吡啶 、 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 氢气 、 镍 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  Stereocontrolled total synthesis of (±)-pisiferol and (±)-pisiferal

  摘要：

  The stereoselective total synthesis of (+/-)-pisiferol (1) and (+/-)-pisiferal (2) has been successfully accomplished using the trans-octahydrophenanthrene derivative 20 as a key intermediate. Intramolecular cyclisation of the diazoketone 15 followed by catalytic hydrogenation provided, stereo selectively, the keto-ester 17 which was converted into the acetate 20 through the intermediates 18 and 19. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.089
• 作为产物：
  描述：

  Methyl 2-(5-diazo-2-methyl-4-oxopentan-2-yl)-4,7-dimethoxynaphthalene-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.05h， 以64%的产率得到Methyl 6-methoxy-1,1-dimethyl-3,9-dioxo-2,4-dihydrophenanthrene-4a-carboxylate
  参考文献：
  名称：

  Stereocontrolled total synthesis of (±)-pisiferol and (±)-pisiferal

  摘要：

  The stereoselective total synthesis of (+/-)-pisiferol (1) and (+/-)-pisiferal (2) has been successfully accomplished using the trans-octahydrophenanthrene derivative 20 as a key intermediate. Intramolecular cyclisation of the diazoketone 15 followed by catalytic hydrogenation provided, stereo selectively, the keto-ester 17 which was converted into the acetate 20 through the intermediates 18 and 19. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.089

文献信息

• Stereocontrolled total synthesis of (±)-pisiferol and (±)-pisiferal
  作者：Lokesh Chandra Pati、Debabrata Mukherjee

  DOI：10.1016/j.tetlet.2004.10.089

  日期：2004.12

  The stereoselective total synthesis of (+/-)-pisiferol (1) and (+/-)-pisiferal (2) has been successfully accomplished using the trans-octahydrophenanthrene derivative 20 as a key intermediate. Intramolecular cyclisation of the diazoketone 15 followed by catalytic hydrogenation provided, stereo selectively, the keto-ester 17 which was converted into the acetate 20 through the intermediates 18 and 19. (C) 2004 Elsevier Ltd. All rights reserved.