3',5'-dibenzyloxy-2'-hydroxy-p-terphenyl | 1026691-86-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3',5'-dibenzyloxy-2'-hydroxy-p-terphenyl
• 英文别名: 3,6-Diphenyl-2,4-bis(phenylmethoxy)phenol
• CAS: 1026691-86-0
• 化学式: C₃₂H₂₆O₃
• 分子量: 458.557
• InChiKey: LAZUKBMGWXAZHY-UHFFFAOYSA-N

物化性质

• 沸点：
  605.4±55.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3',5'-dibenzyloxy-2'-hydroxy-p-terphenyl 在 palladium on activated charcoal 氢气 、 caesium carbonate 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 48.0h， 生成 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(3',5'-dihydroxy-[1,1';4',1'']terphenyl-2'-yloxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  The isolation, structural determination, and total synthesis of terfestatin A, a novel auxin signaling inhibitor from Streptomyces sp.

  摘要：

  Indole 3-acetic acid, a plant hormone auxin, regulates every aspects of plant growth and development. In the screening for specific inhibitors on auxin signaling using the transgenic Arabidopsis plant harboring the auxin-responsive reporter gene, terfestatin A was found to be a novel inhibitor of auxin signaling from the culture of Streptomyces sp. F40. The structure of terfestatin A was determined to be p-terphenyl beta-glucoside on the basis of spectroscopic analyses, chemical degradation, and total synthesis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.055
• 作为产物：
  描述：

  Acetic acid 3',5'-bis-benzyloxy-[1,1';4',1'']terphenyl-2'-yl ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以90%的产率得到3',5'-dibenzyloxy-2'-hydroxy-p-terphenyl
  参考文献：
  名称：

  The isolation, structural determination, and total synthesis of terfestatin A, a novel auxin signaling inhibitor from Streptomyces sp.

  摘要：

  Indole 3-acetic acid, a plant hormone auxin, regulates every aspects of plant growth and development. In the screening for specific inhibitors on auxin signaling using the transgenic Arabidopsis plant harboring the auxin-responsive reporter gene, terfestatin A was found to be a novel inhibitor of auxin signaling from the culture of Streptomyces sp. F40. The structure of terfestatin A was determined to be p-terphenyl beta-glucoside on the basis of spectroscopic analyses, chemical degradation, and total synthesis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.055

文献信息

• Active core structure of terfestatin A, a new specific inhibitor of auxin signaling
  作者：Ken-ichiro Hayashi、Atsushi Yamazoe、Yuki Ishibashi、Naoyuki Kusaka、Yutaka Oono、Hiroshi Nozaki

  DOI：10.1016/j.bmc.2008.02.085

  日期：2008.5

  The auxins, plant hormones, regulate many aspects of the growth and development of plants. Terfestatin A (TrfA), a novel auxin signaling inhibitor, was identified in a screen of Streptomyces sp. F40 extracts for inhibition of the expression of an auxin-inducible gene. However, the mode of action of TrfA has not been elucidated. To identify the active core structure, 25 derivatives of TrfA were synthesized and their inhibitory activities against auxin-inducible gene expression were evaluated. The structure activity relationships revealed the essential active core structure of TrfA, 3-butoxy-4-methylbiphenyl-2,6-diol, which will lead to the design of biotin-tagged active TrfA. (C) 2008 Elsevier Ltd. All rights reserved.
• The isolation, structural determination, and total synthesis of terfestatin A, a novel auxin signaling inhibitor from Streptomyces sp.
  作者：Atsushi Yamazoe、Ken-ichiro Hayashi、Atsuhito Kuboki、Susumu Ohira、Hiroshi Nozaki

  DOI：10.1016/j.tetlet.2004.09.055

  日期：2004.11

  Indole 3-acetic acid, a plant hormone auxin, regulates every aspects of plant growth and development. In the screening for specific inhibitors on auxin signaling using the transgenic Arabidopsis plant harboring the auxin-responsive reporter gene, terfestatin A was found to be a novel inhibitor of auxin signaling from the culture of Streptomyces sp. F40. The structure of terfestatin A was determined to be p-terphenyl beta-glucoside on the basis of spectroscopic analyses, chemical degradation, and total synthesis. (C) 2004 Elsevier Ltd. All rights reserved.