<4-(α-chlorobenzyl)phenoxy>acetic acid | 117175-05-0

• 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: <4-(α-chlorobenzyl)phenoxy>acetic acid
• 英文别名: 4-(α-chlorobenzyl)phenoxyacetic acid；2-(4-(Chloro(phenyl)methyl)phenoxy)aceticacid；2-[4-[chloro(phenyl)methyl]phenoxy]acetic acid
• CAS: 117175-05-0
• 化学式: C₁₅H₁₃ClO₃
• 分子量: 276.719
• InChiKey: CCZPCMCPCVXECT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <4-(α-chlorobenzyl)phenoxy>acetic acid 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 4-(α-mercaptobenzyl)phenoxyacetic acid
  参考文献：
  名称：

  合成用于肽α-硫代酸固相合成的硫酯树脂接头的一般方法

  摘要：

  据报导了用于逐步固相肽合成的硫酯连接基合成的一般方法。接头与Boc化学相容，并且在HF中裂解后，会生成肽C末端硫代酸。

  DOI：

  10.1016/0040-4039(95)00037-d
• 作为产物：
  描述：

  (4-苯甲酰基苯氧基)-乙酸 在 盐酸 、 sodium tetrahydroborate 作用下， 生成 <4-(α-chlorobenzyl)phenoxy>acetic acid
  参考文献：
  名称：

  硫酯连接基前体的合成，用于肽C末端硫代酸的常规制备

  摘要：

  提出了通过固相肽合成制备肽硫代酸的一般程序。该方法包括合成4- [α-（S-乙酰基）巯基苄基]苯氧基乙酸作为一般前体。巯基脱保护后，一旦连接到固体支持物上的该试剂就会用所选的Boc-氨基酸衍生化。

  DOI：

  10.1016/j.tetlet.2003.12.160

文献信息

• A general method for the synthesis of thioester resin linkers for use in the solid phase synthesis of peptide-α-thioacids
  作者：Lynne E. Canne、Sharon M. Walker、Stephen B.H. Kent

  DOI：10.1016/0040-4039(95)00037-d

  日期：1995.2

  A generalized procedure for the synthesis of thioester linkers for use in stepwise solid phase peptide synthesis is reported. The linkers are compatible with Boc chemistry and, upon cleavage in HF, generate peptide C-terminal thioacids.

  据报导了用于逐步固相肽合成的硫酯连接基合成的一般方法。接头与Boc化学相容，并且在HF中裂解后，会生成肽C末端硫代酸。
• US7408026B1
  申请人：——

  公开号：US7408026B1

  公开（公告）日：2008-08-05
• Synthesis of a thioester linker precursor for a general preparation of peptide C-terminal thioacids
  作者：Hubert Gaertner、Matteo Villain、Paolo Botti、Lynne Canne

  DOI：10.1016/j.tetlet.2003.12.160

  日期：2004.3

  A general procedure to prepare peptide thioacids by solid-phase peptide synthesis is presented. The method involves the synthesis of 4-[α-(S-acetyl)mercaptobenzyl]phenoxyacetic acid as general precursor. This reagent once attached to a solid support is derivatized with the Boc-amino acid of choice after deprotection of the thiol.

  提出了通过固相肽合成制备肽硫代酸的一般程序。该方法包括合成4- [α-（S-乙酰基）巯基苄基]苯氧基乙酸作为一般前体。巯基脱保护后，一旦连接到固体支持物上的该试剂就会用所选的Boc-氨基酸衍生化。
• Total Chemical Synthesis of a Unique Transcription Factor-Related Protein: cMyc-Max
  作者：Lynne E. Canne、Adrian R. Ferre- D'Amare、Stephen K. Burley、Stephen B. H. Kent

  DOI：10.1021/ja00116a005

  日期：1995.3

  cMyc and Max are proteins that regulate gene expression by associating to form noncovalent dimers that bind to specific regions of double-stranded DNA, thus activating or inhibiting mRNA transcription. Each of these transcription factor proteins contains an similar to 90 amino acid residue basic/helix-loop-helix/zipper (b/HLH/Z) domain responsible for formation of the protein dimers and for DNA binding. Noncovalent heterodimers of the cMyc and Max b/HLH/Z domains are believed to be functionally important in vivo but have not been accessible by conventional means (recDNA expression). Here we report the total chemical synthesis of novel covalently-linked dimers of the b/HLH/Z domains of these transcription factors by a modular strategy based on the convergent chemical ligation of several unprotected peptide segments. The resulting similar to 20 kDa synthetic proteins were purified to homogeneity and characterized by electrospray mass spectrometry. The synthetic covalent cMyc-Max heterodimer and the covalent Max homodimer control were shown to bind DNA specifically at the region involved in the regulation of mRNA transcription. Access to defined heterodimeric forms of the b/HLH/Z transcription factors will allow the structural and functional properties of these important protein regulators of gene expression to be studied.