4-[(2-氯苯基)(羟基)苯基甲基]苯甲酸 | 172976-68-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: 4-[(2-氯苯基)(羟基)苯基甲基]苯甲酸
• 中文别名: 1H-咪唑,2,5-二氢-2-甲基-2,4-二(1-甲基乙基)-(9CI)
• 英文名称: 2-chloro-4'-carboxytriphenylmethanol
• 英文别名: 4-[(2-Chlorophenyl)(hydroxy)phenylmethyl]benzoic acid；4-[(2-chlorophenyl)-hydroxy-phenylmethyl]benzoic acid
• CAS: 172976-68-0
• 化学式: C₂₀H₁₅ClO₃
• 分子量: 338.79
• InChiKey: MYQCIJNSLZDQDI-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：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(2-氯苯基)(羟基)苯基甲基]苯甲酸 在 乙酰溴 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.25h， 生成 4-[Bromo-(2-chloro-phenyl)-phenyl-methyl]-benzoic acid pentafluorophenyl ester
  参考文献：
  名称：

  Synthesis of the 3-Repeat Region of Human Tau-2 by the Solid Phase Assembly of Backbone Amide-Protected Segments

  摘要：

  The synthesis, purification, and use of N-(2-acetoxy-4-methoxybenzyl)(AcHmb) backbone amide protected segments in the preparation of Asp(158)-Leu(251) from the 3-repeat region of human tau-2 has been investigated. Fmoc/tert-butyl based(1,2) fully protected segments of 9-21 residues, containing appropriately placed AcHmb protection were prepared on Polyhipe SU500 resin through a 2-chlorotrityl linker. Protected segments, cleaved with 0.75% trifluoroacetic acid in dichloromethane, were easily purified in 100s of milligram quantities by either silica gel chromatography or standard aqueous acetonitrile based reverse phase preparative HPLC. Purified protected segments, typically soluble at >500 mg mL(-1) in dimethylformamide, coupled efficiently and economically to a growing resin-bound assembly, to give the 94-mer human tau-2 with an overall purified yield of 2.50 mu mol (16.7%).

  DOI：

  10.1021/ja00152a005
• 作为产物：
  描述：

  2-氯二苯甲酮 、 4-溴苯甲酸 在 正丁基锂 作用下， 以50%的产率得到4-[(2-氯苯基)(羟基)苯基甲基]苯甲酸
  参考文献：
  名称：

  （R，S）2-氟（氯）-4'-羧基-三苯基甲醇。用于固相肽合成的新型酸不稳定的三苯甲基型手柄

  摘要：

  新颖三苯甲基型把手已经制备和应用到使用9固相合成-芴基（Fmoc）进行N-一-氨基保护侧链保护的酸不稳定保护基团和。可以通过使用合适的0.1％（v / v）的三氟乙酸弱酸性混合物和TFE∶CH 2 Cl 2 ∶CH 3 COOH 1∶8∶1 （v / v）来裂解所得的酯。

  DOI：

  10.1016/0040-4039(94)88341-6

文献信息

• Synthesis and assignment of stereochemistry of the antibacterial cyclic peptide xenematide
  作者：Kuo-yuan Hung、Paul W. R. Harris、Amanda M. Heapy、Margaret A. Brimble

  DOI：10.1039/c0ob00315h

  日期：——

  The synthesis of the antimicrobial cyclic peptide xenematide was accomplished by Fmoc solid phase peptide synthesis and the key esterification reaction was achieved using a modified Yamaguchi esterification. Comparison of the optical rotation and NMR data of the synthesized diastereomers to that of the natural product confirmed the structure of xenematide to be PA-L-[Thr-L-Trp-D-Trp-β-Ala]. (PA = phenylacetyl)

  抗菌环肽的合成 塞内马肽通过Fmoc固相肽合成来完成，并且使用改进的Yamaguchi酯化来实现关键的酯化反应。合成的非对映异构体与天然产物的旋光度和核磁共振数据的比较证实了其​​结构塞内马肽是PA-大号- [Thr-大号-Trp- d -Trp-β丙氨酸]。（PA ＝苯乙酰基）。
• (R, S) 2-fluoro (chloro)-4′-carboxy-triphenyl methanol. Novel acid labile trityl type handles for solid phase peptide synthesis
  作者：Christos C. Zikos、Nicolas G. Ferderigos

  DOI：10.1016/0040-4039(94)88341-6

  日期：1994.3

  Novel trityl type handles have been prepared and applied to solid phase synthesis using 9 - fluorenylmethyloxycarbonyl (Fmoc) for Na - amino protection and acid labile protecting groups for side chain protection. The cleavage of the resultant ester can be carried out by using appropriate mild acidic cocktails 0.1 % (v/v) trifluoroacetic acid, and TFE : CH2Cl2 : CH3COOH 1 : 8 : 1 (v/v).

  新颖三苯甲基型把手已经制备和应用到使用9固相合成-芴基（Fmoc）进行N-一-氨基保护侧链保护的酸不稳定保护基团和。可以通过使用合适的0.1％（v / v）的三氟乙酸弱酸性混合物和TFE∶CH 2 Cl 2 ∶CH 3 COOH 1∶8∶1 （v / v）来裂解所得的酯。
• Synthetic Studies towards the Calcium‐Dependent Lipopeptide Antibiotic Cadaside B
  作者：Nadiia Kovalenko、Jonathan A. Swain、Georgina K. Howard、Yann O. Hermant、Alan J. Cameron、Louise A. Stubbing、Paul W. R. Harris、Margaret A. Brimble

  DOI：10.1002/chem.202202554

  日期：2022.12.15

  Cadaside B is a novel calcium-dependent lipopeptide antibiotic, bearing multiple rare non-canonical amino acids and exhibiting potent antimicrobial activity towards multi-drug resistant Gram-positive pathogens. Synthetic studies towards cadaside B yielded a compound possessing the desired connectivity of macrocyclic scaffold, but poorly matching 1H NMR spectra and lack of bioactivity. Insights and

  Cadaside B是一种新型的钙依赖性脂肽抗生素，具有多种稀有的非经典氨基酸，对多重耐药的革兰氏阳性病原体表现出强大的抗菌活性。对 cadaside B 的合成研究产生了一种化合物，该化合物具有所需的大环骨架连接性，但1 H NMR 光谱匹配不佳且缺乏生物活性。提出了对全合成的见解和挑战。
• Amphiphilic solid support
  申请人：Polymer Laboratories Limited

  公开号：EP2159228A1

  公开（公告）日：2010-03-03

  Amphiphilic solid supports for solid phase synthesis are disclosed, and methods for preparation and use thereof, comprising a solid support and a compound according to Formula I covalently bound thereto: wherein A is C5-10 aryl or heteroaryl, Z is either lower alkyl or absent, R1 is lower alkyl, R2 is H or lower alkyl, a is an integer from about 0 to about 20, b is an integer from about 5 to about 150, c is an integer from about 0 to about 20.

  本发明公开了用于固相合成的两亲性固体支持物及其制备和使用方法，包括固体支持物和与之共价结合的符合式 I 的化合物： 其中 A 是 C5-10 芳基或杂芳基，Z 是低级烷基或不存在，R1 是低级烷基，R2 是 H 或低级烷基，a 是约 0 至约 20 的整数，b 是约 5 至约 150 的整数，c 是约 0 至约 20 的整数。
• Synthesis of the 3-Repeat Region of Human Tau-2 by the Solid Phase Assembly of Backbone Amide-Protected Segments
  作者：M. Quibell、L. C. Packman、T. Johnson

  DOI：10.1021/ja00152a005

  日期：1995.11

  The synthesis, purification, and use of N-(2-acetoxy-4-methoxybenzyl)(AcHmb) backbone amide protected segments in the preparation of Asp(158)-Leu(251) from the 3-repeat region of human tau-2 has been investigated. Fmoc/tert-butyl based(1,2) fully protected segments of 9-21 residues, containing appropriately placed AcHmb protection were prepared on Polyhipe SU500 resin through a 2-chlorotrityl linker. Protected segments, cleaved with 0.75% trifluoroacetic acid in dichloromethane, were easily purified in 100s of milligram quantities by either silica gel chromatography or standard aqueous acetonitrile based reverse phase preparative HPLC. Purified protected segments, typically soluble at >500 mg mL(-1) in dimethylformamide, coupled efficiently and economically to a growing resin-bound assembly, to give the 94-mer human tau-2 with an overall purified yield of 2.50 mu mol (16.7%).