trans-2-(benzyloxycarbonylamino)cyclohexanecarboxylic acid | 61935-48-6

• 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: trans-2-(benzyloxycarbonylamino)cyclohexanecarboxylic acid
• 英文别名: trans-1-(Benzyloxycarbonyl-amino)-cyclohexyl-2-carboxylic acid；(1S,2S)-2-(phenylmethoxycarbonylamino)cyclohexane-1-carboxylic acid
• CAS: 61935-48-6
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: RPJMLWMATNCSIS-STQMWFEESA-N

物化性质

• 熔点：
  146-148 °C(Solv: methanol (67-56-1))
• 沸点：
  484.7±44.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  trans-2-(benzyloxycarbonylamino)cyclohexanecarboxylic acid 在 palladium on activated charcoal 氨 、 氢气 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 乙醇 为溶剂， -10.0~25.0 ℃ 、101.33 kPa 条件下， 反应 17.25h， 生成 trans-2-aminocyclohexanecarboxamide
  参考文献：
  名称：

  Goendoes, Gyoergy; Szecsenyi, Istvan; Dombi, Gyoergy, Liebigs Annalen der Chemie, 1991, # 6, p. 591 - 593

  摘要：

  DOI：
• 作为产物：
  描述：

  (4S)-N-benzyloxycarbonyl-4-allyl-1,3-oxazinan-6-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium 10% on activated carbon 、 氢气 、 双(三甲基硅烷基)氨基钾 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 7.67h， 生成 trans-2-(benzyloxycarbonylamino)cyclohexanecarboxylic acid
  参考文献：
  名称：

  Diastereoselective synthesis of cyclic β2,3-amino acids utilizing 4-substituted-1,3-oxazinan-6-ones

  摘要：

  The 4-substituted-1,3-oxazinan-6-one scaffold is a versatile synthon enabling access to a diverse array of beta-amino acid derivatives. In this study, the synthetic utility of the 1,3-oxazinan-6-one is expanded to include the diastereoselective synthesis of cyclic beta(2,3)-amino acids. Enolate chemistry is used to first alkylate the 4-vinyl, 4-allyl, and 4-butenyl oxazinan-6-ones with various alkenyl electrophiles, in high dr. The resulting 4,5-bis-alkene adducts are then transformed into 4,5-cyclic-1,3-oxazinan-6-ones utilizing the ring closing metathesis reaction. The metathesis products are subsequently converted into a variety of five-, six-, and seven-membered cyclic beta(2,3)-amino acids. The research further highlights the 1,3-oxazinan-6-one as a versatile synthon for producing beta-amino acid derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.016

文献信息

• INHIBITORS OF INFLUENZA VIRUSES REPLICATION
  申请人：Charifson Paul S.

  公开号：US20120171245A1

  公开（公告）日：2012-07-05

  Methods of inhibiting the replication of influenza viruses in a biological sample or patient, of reducing the amount of influenza viruses in a biological sample or patient, and of treating influenza in a patient, comprises administering to said biological sample or patient an effective amount of a compound represented by Structural Formula (I): or a pharmaceutically acceptable salt thereof, wherein the values of Structural Formula (IA) are as described herein. A compound is represented by Structural Formula (IA) or a pharmaceutically acceptable salt thereof, wherein the values of Structural Formula (IA) are as described herein. A pharmaceutical composition comprises an effective amount of such a compound or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, adjuvant or vehicle.

  抑制生物样本或患者中流感病毒的复制、减少生物样本或患者中流感病毒量以及治疗患者流感的方法，包括向所述生物样本或患者施用有效量的由结构公式（I）表示的化合物： 或其药用可接受盐，其中结构公式（IA）的值如本文所述。由结构公式（IA）或其药用可接受盐表示的化合物，其中结构公式（IA）的值如本文所述。药物组合物包括有效量的上述化合物或其药用可接受盐，以及药用可接受载体、佐剂或车辆。
• A novel, microwave-assisted method for the synthesis of alicyclic-condensed 5H-1,4,6,7-tetrahydro-1,4-diazepin-5-ones
  作者：Árpád Balázs、Erik Van der Eycken、Ferenc Fülöp

  DOI：10.1016/j.tetlet.2008.05.034

  日期：2008.7

  An efficient, high-yielding method has been developed for the synthesis of cycloalkane-fused and phenyl-substituted 1,4-diazepin-5-ones from β-amino acids. The process involves the oxidative cleavage of a terminal olefin bond and an acid-catalyzed, microwave-assisted intramolecular condensation step.

  已经开发了一种高效，高产率的方法，用于从β-氨基酸合成环烷烃稠合的和苯基取代的1,4-二氮杂5-5-酮。该方法涉及末端烯烃键的氧化裂解和酸催化的，微波辅助的分子内缩合步骤。
• Dipeptidyl aspartyl fluoromethylketones as potent caspase inhibitors: Peptidomimetic replacement of the P2 amino acid by 2-aminoaryl acids and other non-natural amino acids
  作者：Yan Wang、Shaojuan Jia、Ben Tseng、John Drewe、Sui Xiong Cai

  DOI：10.1016/j.bmcl.2007.09.030

  日期：2007.11

  As a continuation of our SAR studies of dipeptidyl aspartyl-fmk as caspase inhibitors, we explored the replacement of the P(2) amino acid by a 2-aminoaryl acid or other non-natural amino acids. Several of these compounds, such as 6l and 6p, were found to have good activities with inhibition potencies of around 100 nM in a caspase-3 enzyme assay. EP1113, Z-Val-(2-aminobenzoyl)-Asp-fmk (9b), is identified

  作为我们对作为天冬氨酸蛋白酶抑制剂的二肽基天冬氨酰-fmk的SAR研究的延续，我们探索了用2-氨基芳基酸或其他非天然氨基酸替代P（2）氨基酸。在caspase-3酶分析中，发现其中的几种化合物（例如6l和6p）具有良好的活性，抑制力约为100 nM。EP1113 Z-Val-（2-氨基苯甲酰基）-Asp-fmk（9b）被确定为有效的广谱胱天蛋白酶抑制剂，在不同的半胱天冬酶中IC（50）值为6-60 nM。EP1113在细胞凋亡保护试验中也具有良好的活性。
• 1,2-Disubstituted cyclohexane derived tripeptide aldehydes as novel selective thrombin inhibitors
  作者：Nicholas J.S. Harmat、Cristina Di Bugno、M. Criscuoli、Raffaello Giorgi、Annalisa Lippi、Adriano Martinelli、Susanna Monti、A. Subissi

  DOI：10.1016/s0960-894x(98)00200-5

  日期：1998.5

  A series of tripeptide arginine aldehydes was synthesized by replacement of proline with 1,2-disubstituted cyclohexane derivatives in the sequence of D-MePhe-Pro-Arg-H. Based on molecular modeling, further modification of the D-MePhe residue resulted in a potent and selective thrombin inhibitor.

  通过用D-MePhe-Pro-Arg-H序列中的1，2-二取代的环己烷衍生物代替脯氨酸，合成了一系列的三肽精氨酸醛。基于分子模型，D-MePhe残基的进一步修饰产生了有效的选择性凝血酶抑制剂。
• Ring−Chain Tautomerism of 2-Aryl-Substituted <i>cis</i>- and <i>trans</i>-Decahydroquinazolines
  作者：László Lázár、Anikó Göblyös、Tamás A. Martinek、Ferenc Fülöp

  DOI：10.1021/jo020070j

  日期：2002.7.1

  and trans-3-phenyldecahydroquinazolines proved to be three-component (r(1)[bond]o[bond]r(2)) ring[bond]chain tautomeric mixtures, whereas only ring-closed tautomers could be detected for the 3-methyl-substituted analogues. The proportions of the ring-chain tautomeric forms at equilibrium were strongly influenced by the N-substitutents and the cis-trans ring junction and could be described by the equation

  在300 K的CDCl（3）中，2-芳基取代的顺式和反式-3-异丙基十氢喹唑啉和反式-3-苯基十氢喹唑啉被证明是三组分的（r（1）[o] bon [r]（2） ）环链互变异构混合物，而对于3-甲基取代的类似物只能检测到闭环互变异构体。N-取代基和顺-反式环结强烈影响着平衡状态下的环链互变异构形式的比例，可用等式log K（X）= rho sigma（+）+ log K（X = H）。这些是由哈米特型方程表征的三组分环链互变异构平衡的2-芳基-1,3-N，N-杂环中的第一个实例。顺式和反式-2-芳基十氢喹唑啉的闭环形式的稳定性以及相应的3，