dimethyl 2-(4'-acetoxyoct-2'(E)-enyl)-2-(4"-methylbenzyl)malonate | 462128-81-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dimethyl 2-(4'-acetoxyoct-2'(E)-enyl)-2-(4"-methylbenzyl)malonate
• 英文别名: dimethyl 2-[(E)-4-acetyloxyoct-2-enyl]-2-[(4-methylphenyl)methyl]propanedioate
• CAS: 462128-81-0
• 化学式: C₂₃H₃₂O₆
• 分子量: 404.503
• InChiKey: OJXZXMABMWRVMW-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(4'-acetoxyoct-2'(E)-enyl)-2-(4"-methylbenzyl)malonate 在 三氟乙酸 作用下， 以 溶剂黄146 为溶剂， 反应 1.5h， 以99%的产率得到2,2-bis(methoxycarbonyl)-6-methyl-4-hex-1'(E)-enyl-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Efficient synthesis of benzocyclohexanes via intramolecular Friedel–Crafts reaction of halogen free 6-acetoxy-4-alkenyl arenes

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(02)00430-6
• 作为产物：
  描述：

  dimethyl 2-(4-methylbenzyl)malonate 在 4-二甲氨基吡啶 、 palladium diacetate 、 sodium hydride 、 三乙胺 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 dimethyl 2-(4'-acetoxyoct-2'(E)-enyl)-2-(4"-methylbenzyl)malonate
  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

• 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.
• TFA-mediated intramolecular Friedel–Crafts reaction. An efficient metal and halogen free route to stereoselective synthesis of benzocycles
  作者：Shengming Ma、Junliang Zhang

  DOI：10.1016/s0040-4020(03)01026-3

  日期：2003.8

  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.