rac,cis-2-(9-fluorenylmethoxycarbonylamino)-cyclohex-3-ene carboxylic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: rac,cis-2-(9-fluorenylmethoxycarbonylamino)-cyclohex-3-ene carboxylic acid
• 英文别名: (1S,2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)cyclohex-3-ene-1-carboxylic acid
• 化学式: C₂₂H₂₁NO₄
• 分子量: 363.413
• InChiKey: OTYJADWWVDSUOQ-AZUAARDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-2-(9-Fluorenylmethoxycarbonylamino)cyclohex-3-enecarboxylic acid 、 rac,cis-2-(9-fluorenylmethoxycarbonylamino)-cyclohex-3-ene carboxylic acid 在 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 3.0h， 以48%的产率得到
  参考文献：
  名称：

  Building β-Peptide H10/12 Foldamer Helices with Six-Membered Cyclic Side-Chains: Fine-Tuning of Folding and Self-Assembly

  摘要：

  The ability of the beta-peptidic H10/12 helix to tolerate side-chains containing six-membered alicyclic rings was studied. cis-2-Aminocyclohex-3-ene carboxylic acid (cis-ACHEC) res dues afforded H10/12 helix formation with alternating backbone configuration. Conformational polymorphism was observed for the alternating cis-ACHC hexamer, where chemical exchange takes place between the major left-handed H10/12 helix and a minor folded conformation. The hydrophobically driven self-assembly was achieved for the cis-ACHC-containing helix which was observed as vesicles similar to 100 nm in diameter.

  DOI：

  10.1021/ol102494m
• 作为产物：
  描述：

  7-azabicyclo[4.2.0]oct-4-en-8-one 在 盐酸 、 4-二甲氨基吡啶 、 lithium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 16.83h， 生成 rac,cis-2-(9-fluorenylmethoxycarbonylamino)-cyclohex-3-ene carboxylic acid
  参考文献：
  名称：

  Structure-Based Design, Synthesis, and X-ray Crystallography of a High-Affinity Antagonist of the Grb2-SH2 Domain Containing an Asparagine Mimetic

  摘要：

  Previous efforts in the search for molecules capable of blocking the associations between the activated tyrosine kinase growth factor receptors and the SH2 domain of Grb2 had resulted in the identification of 3-amino-Z-pTyr-Ac(6)c-Asn-NH2, a high-affinity and selective antagonist of this SH2 domain. In the present paper, we report the successful replacement of asparagine in this compound by a beta-amino acid mimetic, which brings us closer to our objective of identifying a Grb2-SH2 antagonist suitable for pharmacological investigations.

  DOI：

  10.1021/jm991013u

文献信息

• Structure-Based Design, Synthesis, and X-ray Crystallography of a High-Affinity Antagonist of the Grb2-SH2 Domain Containing an Asparagine Mimetic
  作者：Pascal Furet、Carlos García-Echeverría、Brigitte Gay、Joseph Schoepfer、Martin Zeller、Joseph Rahuel

  DOI：10.1021/jm991013u

  日期：1999.7.1

  Previous efforts in the search for molecules capable of blocking the associations between the activated tyrosine kinase growth factor receptors and the SH2 domain of Grb2 had resulted in the identification of 3-amino-Z-pTyr-Ac(6)c-Asn-NH2, a high-affinity and selective antagonist of this SH2 domain. In the present paper, we report the successful replacement of asparagine in this compound by a beta-amino acid mimetic, which brings us closer to our objective of identifying a Grb2-SH2 antagonist suitable for pharmacological investigations.
• Building β-Peptide H10/12 Foldamer Helices with Six-Membered Cyclic Side-Chains: Fine-Tuning of Folding and Self-Assembly
  作者：István M. Mándity、Livia Fülöp、Elemér Vass、Gábor K. Tóth、Tamás A. Martinek、Ferenc Fülöp

  DOI：10.1021/ol102494m

  日期：2010.12.3

  The ability of the beta-peptidic H10/12 helix to tolerate side-chains containing six-membered alicyclic rings was studied. cis-2-Aminocyclohex-3-ene carboxylic acid (cis-ACHEC) res dues afforded H10/12 helix formation with alternating backbone configuration. Conformational polymorphism was observed for the alternating cis-ACHC hexamer, where chemical exchange takes place between the major left-handed H10/12 helix and a minor folded conformation. The hydrophobically driven self-assembly was achieved for the cis-ACHC-containing helix which was observed as vesicles similar to 100 nm in diameter.