1-vinyl-3,3-bis(methoxycarbonyl)-1,2,3,4-tetrahydrophenanthrene

• 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: 1-vinyl-3,3-bis(methoxycarbonyl)-1,2,3,4-tetrahydrophenanthrene
• 英文别名: dimethyl 1-ethenyl-2,4-dihydro-1H-phenanthrene-3,3-dicarboxylate
• 化学式: C₂₀H₂₀O₄
• 分子量: 324.376
• InChiKey: BIOPWSGFHJCDNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (氯甲基)萘 在 sodium hydride 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 1-vinyl-3,3-bis(methoxycarbonyl)-1,2,3,4-tetrahydrophenanthrene
  参考文献：
  名称：

  TFA-mediated intramolecular Friedel–Crafts reaction. An efficient metal and halogen free route to stereoselective synthesis of benzocycles

  摘要：

  6-Acetoxy-4-alkenyl arenes undergo regio- and stereoselective intramolecular Friedel-Crafts reaction affording benzocycles in moderate to excellent yields in TFA/HOAc (3: 1). It was observed that introduction of alkyls or phenyl group to the allylic acetate moiety facilitates the cyclization reaction. The optically active tricyclic (4bR,8aS)-4b,7,8,8a,9,10-hexahydrophenanthrene skeleton could also be easily obtained in excellent yields. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01026-3

文献信息

• Gold(I)-Catalyzed Intramolecular Hydroarylation of Allenes
  作者：Michael A. Tarselli、Michel R. Gagné

  DOI：10.1021/jo7024948

  日期：2008.3.1

  Gold(I) complexes react with 4-allenyl arenes in an exo fashion to furnish vinyl-substituted benzocycles. Phosphite gold(I) monocations were found to be optimal, and the catalyst was tolerant of ethers, esters, and pyrroles. Reactions proceeded in unpurified solvent at room temperature.
• Efficient synthesis of benzocyclohexanes via intramolecular Friedel–Crafts reaction of halogen free 6-acetoxy-4-alkenyl arenes
  作者：Shengming Ma、Junliang Zhang

  DOI：10.1016/s0040-4039(02)00430-6

  日期：2002.4

  Benzocyclohexane derivatives were prepared highly stereoselectively by the cyclic Friedel-Crafts reaction of 6-acetoxy-4-alkenyl arenes in moderate to excellent yields in TFA HOAc (3:1). It was observed that the rate of the cyclization as well as the yields of products depend largely on the substituents of the allylic acetate moiety. (C) 2002 Elsevier Science Ltd. All rights reserved.