geranylgeranyl phenyl ether | 1187618-75-2

• 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: geranylgeranyl phenyl ether
• 英文别名: [(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoxy]benzene
• CAS: 1187618-75-2
• 化学式: C₂₆H₃₈O
• 分子量: 366.587
• InChiKey: PANAMZSWGYOVOQ-GHDNBGIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  geranylgeranyl phenyl ether 在 Zymomonas mobilis squalene hopene cyclase 1 作用下， 以 二甲基亚砜 为溶剂， 反应 20.0h， 以5%的产率得到
  参考文献：
  名称：

  Stereoselective Friedel–Crafts alkylation catalyzed by squalene hopene cyclases

  摘要：

  In organic synthesis the Friedel-Crafts alkylation is of eminent importance, as it is a key reaction in many synthetic routes. A general access to enzymatic Friedel-Crafts alkylations would be very beneficial due to the high selectivity of biocatalysts. We used designed polyprenyl phenyl ethers to specifically address this reaction by using squalene hopene cyclases as catalysts. Polycyclic products with aromatic rings constituting important biological active compounds were obtained. Our results demonstrate that squalene hopene cyclases can be utilized for Friedel Crafts alkylations and reveal the potential of these enzymes for chiral Bronsted acid catalysis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.041
• 作为产物：
  描述：

  香叶基香叶醇 在 三溴化磷 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 geranylgeranyl phenyl ether
  参考文献：
  名称：

  Stereoselective Friedel–Crafts alkylation catalyzed by squalene hopene cyclases

  摘要：

  In organic synthesis the Friedel-Crafts alkylation is of eminent importance, as it is a key reaction in many synthetic routes. A general access to enzymatic Friedel-Crafts alkylations would be very beneficial due to the high selectivity of biocatalysts. We used designed polyprenyl phenyl ethers to specifically address this reaction by using squalene hopene cyclases as catalysts. Polycyclic products with aromatic rings constituting important biological active compounds were obtained. Our results demonstrate that squalene hopene cyclases can be utilized for Friedel Crafts alkylations and reveal the potential of these enzymes for chiral Bronsted acid catalysis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.041

文献信息

• Stereoselective Friedel–Crafts alkylation catalyzed by squalene hopene cyclases
  作者：Stephan C. Hammer、Jörg M. Dominicus、Per-Olof Syrén、Bettina M. Nestl、Bernhard Hauer

  DOI：10.1016/j.tet.2012.06.041

  日期：2012.9

  In organic synthesis the Friedel-Crafts alkylation is of eminent importance, as it is a key reaction in many synthetic routes. A general access to enzymatic Friedel-Crafts alkylations would be very beneficial due to the high selectivity of biocatalysts. We used designed polyprenyl phenyl ethers to specifically address this reaction by using squalene hopene cyclases as catalysts. Polycyclic products with aromatic rings constituting important biological active compounds were obtained. Our results demonstrate that squalene hopene cyclases can be utilized for Friedel Crafts alkylations and reveal the potential of these enzymes for chiral Bronsted acid catalysis. (C) 2012 Elsevier Ltd. All rights reserved.