(1R,2R)-1-(hydroxymethyl)-2-(aminomethyl)cyclopentane | 1509907-36-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R)-1-(hydroxymethyl)-2-(aminomethyl)cyclopentane
• CAS: 1509907-36-1
• 化学式: C₇H₁₅NO
• 分子量: 129.202
• InChiKey: VKTXOELOSJCFDK-BQBZGAKWSA-N

物化性质

• 沸点：
  222.9±13.0 °C(Predicted)
• 密度：
  0.978±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.35
• 重原子数：
  9.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.25
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1-(hydroxymethyl)-2-(aminomethyl)cyclopentane 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 重铬酸 、 1-羟基苯并三唑 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 47.0h， 生成
  参考文献：
  名称：

  Evaluation of a Cyclopentane-Based γ-Amino Acid for the Ability to Promote α/γ-Peptide Secondary Structure

  摘要：

  We report the asymmetric synthesis of the gamma-amino acid (1R,2R)-2-aminomethyl-1-cyclopentane carboxylic acid (AMCP) and an evaluation of this residue's potential to promote secondary structure in alpha/gamma-peptides. Simulated annealing calculations using NMR-derived distance restraints obtained for alpha/gamma-peptides in chloroform reveal that AMCP-containing oligomers are conformationally flexible. However, additional evidence suggests that an internally hydrogen-bonded helical conformation is partially populated in solution. From these data, we propose characteristic NOE patterns for the formation of the alpha/gamma-peptide 12/10-helix and discuss the apparent conformational frustration of AMCP-containing oligomers.

  DOI：

  10.1021/jo401501g
• 作为产物：
  描述：

  1-环戊烯甲醛 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 sodium tetrahydroborate 、 氢气 、 苯甲酸 作用下， 以 2,4,6-三甲基吡啶 、 甲醇 、 乙醇 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 18.0h， 生成 (1R,2R)-1-(hydroxymethyl)-2-(aminomethyl)cyclopentane
  参考文献：
  名称：

  Evaluation of a Cyclopentane-Based γ-Amino Acid for the Ability to Promote α/γ-Peptide Secondary Structure

  摘要：

  We report the asymmetric synthesis of the gamma-amino acid (1R,2R)-2-aminomethyl-1-cyclopentane carboxylic acid (AMCP) and an evaluation of this residue's potential to promote secondary structure in alpha/gamma-peptides. Simulated annealing calculations using NMR-derived distance restraints obtained for alpha/gamma-peptides in chloroform reveal that AMCP-containing oligomers are conformationally flexible. However, additional evidence suggests that an internally hydrogen-bonded helical conformation is partially populated in solution. From these data, we propose characteristic NOE patterns for the formation of the alpha/gamma-peptide 12/10-helix and discuss the apparent conformational frustration of AMCP-containing oligomers.

  DOI：

  10.1021/jo401501g

文献信息

• A slightly shorter route to carbocyclic nucleosides. Synthesis of (±)-<i>trans</i>-1-[2-(hydroxymethyl)cyclopentylmethyl]uracil
  作者：Lourdes Santana、Marta Teijeira、Eugenio Uriarte

  DOI：10.1002/jhet.5570360146

  日期：1999.1

  (±)-trans-1-[2-(Hydroxymethyl)cyclopentylmethyl]uracil (1) was prepared in two steps and 56% yield from 2-hydroxymethylcyclopentylmethylamine (7) and 3-methoxy-2-propenoylisocyanate (6). Isocyanate 6 was prepared from methyl 3-methoxy-2-propenoate in four steps and 38% overall yield.

  分两步制备（±）-反式-1- [2-（羟甲基）环戊基甲基]尿嘧啶（1），由2-羟甲基环戊基甲胺（7）和3-甲氧基-2-丙烯酰基异氰酸酯（6）制备产率为56％。由3-甲氧基-2-丙烯酸甲酯以四个步骤制备异氰酸酯6，总产率为38％。
• A Novel Approach for the Virtual Screening and Rational Design of Anticancer Compounds
  作者：Ernesto Estrada、Eugenio Uriarte、Alina Montero、Marta Teijeira、Lourdes Santana、Erik De Clercq

  DOI：10.1021/jm991172d

  日期：2000.5.1

  A topological substructural approach to molecular design (TOSS-MODE) has been introduced for the selection and design of anticancer compounds. A quantitative model that discriminates anticancer compounds from the inactive ones in a training series was obtained. This model permits the correct classification of 91.43% of compounds in an external prediction set with only 1.43% of false actives and 7.14% of false inactives. The model developed is then used in a simulation of a virtual search for Ras FTase inhibitors; 87% of the Ras FTase inhibitors used in this simulated search were correctly classified, thus indicating the ability of the TOSS-MODE model of finding lead compounds with novel structures and mechanism of action. Finally, a series of carbonucleosides was designed, and the compounds were classified as active/inactive anticancer compounds by using the model developed here. From the compounds so-designed, 20 were synthesized and evaluated experimentally for their antitumor effects on the proliferation of murine leukemia cells (L1210/0) and human T-lymphocyte cells (Molt4/C8 and CEM/0); 80% of these compounds were well-classified, as active or inactive, and only two pairs of isomeric compounds were false actives. The chloropurine derivatives were the most active compounds, especially compounds 6c,d.
• 1,2-Disubstituted Carbocyclic Analogues of Thymine Nucleosides
  作者：V. Escuredo、B. Ferro、L. Santana、M. Teijeira、E. Uriarte

  DOI：10.1080/07328319708006204

  日期：1997.7

  A series of one two carbonucleoside (OTC) analogues of thymine was synthetized and their conformation was studied by AM1 theoretical calculations. The low-energy conformations of Compound 1 and 2',3'-dideoxythymidine, showed a degree of steric congruity.
• Synthesis and Biological Evaluation of 1,2-Disubstituted Carbonucleosides of 6-Substituted Purine and 8-Azapurine
  作者：L. Santana、M. Teijeira、E. Uriarte、C. Terán、G. Andrei、R. Snoeck、J. Balzarini、E. De Clercq

  DOI：10.1080/15257779908041557

  日期：1999.4

  A series of new one two subtituted carbonucleoside analogues (OTC), with the purine and 8-azapurine base linked through a methylene group at the cyclopentane ring, were synthesized and evaluated for their activity against a number of viruses and tumor cells in vitro.