(+/-)-4,4',5,5',6,6'-Hexakis-benzyloxy-2,2'-bis-hydroxymethyl-biphenyl | 97152-41-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: (+/-)-4,4',5,5',6,6'-Hexakis-benzyloxy-2,2'-bis-hydroxymethyl-biphenyl
• 英文别名: [2-[6-(hydroxymethyl)-2,3,4-tris(phenylmethoxy)phenyl]-3,4,5-tris(phenylmethoxy)phenyl]methanol
• CAS: 97152-41-5
• 化学式: C₅₆H₅₀O₈
• 分子量: 851.008
• InChiKey: MHNDTVPRCAPTDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  64
• 可旋转键数：
  21
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  95.8
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (+/-)-4,4',5,5',6,6'-Hexakis-benzyloxy-2,2'-bis-hydroxymethyl-biphenyl 在 三溴化磷 作用下， 生成 2,2',3,3'4,4'-hexakis(benzyloxy)-1,1'-biphenyl-6,6'-dimethanol dimethyl ether
  参考文献：
  名称：

  Configuratio, Conformation and Rotatory Dispersion of Optically Active Biaryls

  摘要：

  DOI：

  10.1021/ja00867a023
• 作为产物：
  描述：

  鞣花酸 在 lithium aluminium tetrahydride 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 18.0h， 生成 (+/-)-4,4',5,5',6,6'-Hexakis-benzyloxy-2,2'-bis-hydroxymethyl-biphenyl
  参考文献：
  名称：

  Kashiwada; Huang; Ballas, Journal of Medicinal Chemistry, 1994, vol. 37, # 1, p. 195 - 200

  摘要：

  DOI：

文献信息

• Synthesis and biological profiling of tellimagrandin I and analogues reveals that the medium ring can significantly modulate biological activity
  作者：Shaojun Zheng、Luca Laraia、Cornelius J. O' Connor、David Sorrell、Yaw Sing Tan、Zhaochao Xu、Ashok R. Venkitaraman、Wenjun Wu、David R. Spring

  DOI：10.1039/c2ob25065a

  日期：——

  A novel synthesis of the ellagitannin natural product tellimagrandin I and a series of medium ring analogues is described. These compounds were all subsequently screened for redox activity, ability to precipitate protein and cellular phenotype in HeLa cells. From this we have shown that all properties can be modulated independently by varying ring size and by moving the ester out of conjugation with the biaryl ring system. Increasing ring size increased redox activity and cytotoxicity, leading to the identification of a compound (10) which was significantly more cytotoxic. In addition compounds identified with a redox active scaffold and low cytotoxicity may be employed as a new class of redox probes.

  本文描述了一种新的合成方法，用于制备原天然物质ellagitannin的tellimagrandin I及其一系列中等环系类似物。随后对这些化合物进行了氧化还原活性、蛋白质沉淀能力和在HeLa细胞中的细胞表型的筛选。结果表明，通过改变环的大小和将酯基移出联芳环系统的共轭结构，可以独立调控所有这些性质。环的增大增加了氧化还原活性和细胞毒性，从而鉴定出一种化合物（10），其细胞毒性显著更高。此外，具有氧化还原活性骨架和低细胞毒性的化合物可能被用作一类新的氧化还原探针。
• Synthesis of Chiral and Modifiable Hexahydroxydiphenoyl Compounds
  作者：Noriaki Asakura、Shohei Fujimoto、Naoki Michihata、Kentaro Nishii、Hiroshi Imagawa、Hidetoshi Yamada

  DOI：10.1021/jo201750d

  日期：2011.12.2

  A reliable method for synthesizing each enantiomer of the hexahydroxydiphenoyl (HHDP) cornpounds has been developed. The synthesis involved atropselective construction of the aryl-aryl bond of the HHDP compounds. This construction relied on the CuCl2.n-BuNH2-mediated intramolecular coupling of bis (4-O-benzyl- gallate) on two simple chiral auxiliaries, both of which were derived from L-(+)-tartaric acid. The coupling reaction realized complete or near-perfect atropselectivity. The two auxiliaries induced opposite axial chirality despite their identical origin. The diastereoselectivities of these couplings were probably controlled kinetically. Modifications of the free phenolic hydroxy groups and the carbonyl groups in the resulting HHDP compounds demonstrated the potential derivatization of a wide variety of HHDP analogues.
• Kashiwada Yoshiki, Huang Li, Kikuskie Robert E., Bodner Anne J., Lee Kuo-+, Bioorg. and med. chem. lett., 2 (1992) N 3, S 235-238
  作者：Kashiwada Yoshiki, Huang Li, Kikuskie Robert E., Bodner Anne J., Lee Kuo-+

  DOI：——

  日期：——
• Kashiwada Yoshiki, Huang Li, Ballas Lawrence M., Jiang Jack B., Janzen Wi+, J. Med. Chem, 37 (1994) N 1, S 195-200
  作者：Kashiwada Yoshiki, Huang Li, Ballas Lawrence M., Jiang Jack B., Janzen Wi+

  DOI：——

  日期：——
• Kashiwada; Huang; Ballas, Journal of Medicinal Chemistry, 1994, vol. 37, # 1, p. 195 - 200
  作者：Kashiwada、Huang、Ballas、Jiang、Janzen、Lee

  DOI：——

  日期：——