(S)-n-羰基苄氧基环己基氨基丙醇 | 113828-85-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-n-羰基苄氧基环己基氨基丙醇
• 英文名称: Cbz-3-cyclohexyl-L-alaninol
• 英文别名: (S)-N-Carbobenzyloxy cyclohexylalaninol；benzyl N-[(2S)-1-cyclohexyl-3-hydroxypropan-2-yl]carbamate
• CAS: 113828-85-6
• 化学式: C₁₇H₂₅NO₃
• 分子量: 291.39
• InChiKey: XZVBJGVFEUPWEW-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-n-羰基苄氧基环己基氨基丙醇 在 三氧化硫吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 氨甲酸,(2-环己基-1-甲酰基乙基)-,苯基甲基酯,(S)-
  参考文献：
  名称：

  Stereoselective silver triflate-mediated iodocyclization of carbamates

  摘要：

  Iodocyclization of carbamates involving electron-deficient olefins, (i.e. alpha,beta-unsaturated esters) is greatly facilitated by the use of silver(I) triflate and proceeds with excellent trans ring stereoselectivity. During this process, the resultant iodides can undergo epimerization, the rate of which is solvent-dependent.

  DOI：

  10.1016/s0040-4039(00)74232-8
• 作为产物：
  描述：

  CBZ-L-环己基丙氨酸 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-n-羰基苄氧基环己基氨基丙醇
  参考文献：
  名称：

  Stereoselective silver triflate-mediated iodocyclization of carbamates

  摘要：

  Iodocyclization of carbamates involving electron-deficient olefins, (i.e. alpha,beta-unsaturated esters) is greatly facilitated by the use of silver(I) triflate and proceeds with excellent trans ring stereoselectivity. During this process, the resultant iodides can undergo epimerization, the rate of which is solvent-dependent.

  DOI：

  10.1016/s0040-4039(00)74232-8

文献信息

• Tunable Probes with Direct Fluorescence Signals for the Constitutive and Immunoproteasome
  作者：Christian Dubiella、Haissi Cui、Michael Groll

  DOI：10.1002/anie.201605753

  日期：2016.10.10

  leaving group. The use of fluorophores as leaving groups enabled us to design probes that release a stoichiometric fluorescence signal upon reaction, thereby directly linking proteasome inactivation to the readout. This principle could be applicable to other sulfonyl fluoride based inhibitors and allows the design of sensitive probes for enzymatic studies.

  亲电试剂通常用于抑制蛋白酶。值得注意的是，蛋白酶体抑制剂是细胞存活的关键因素，也是几种FDA批准药物的靶标，其主要特征是亲电头基的反应性。我们旨在通过改变离去基团来调节肽磺酸酯的抑制强度。确实，蛋白酶体抑制与离去基团的p K a密切相关。使用荧光团作为离去基团使我们能够设计探针，该探针在反应后释放化学计量的荧光信号，从而直接将蛋白酶体失活与读数联系起来。该原理可能适用于其他基于磺酰氟的抑制剂，并允许设计用于酶研究的敏感探针。
• [EN] PROTEASOME INHIBITOR COMPRISING A SIGNAL-EMITTING MOIETY<br/>[FR] INHIBITEUR DE PROTÉASOME COMPRENANT UNE FRACTION D'ÉMISSION DE SIGNAL
  申请人：TECHNISCHE UNIVERSITÄT MÜNCHEN

  公开号：WO2017032487A1

  公开（公告）日：2017-03-02

  The present invention relates to compounds such as peptides which act as proteasome inhibitors. The compounds are covalently linked with a signal emitting compound or a precursor thereof, via an ester such as a sulfonic ester group for imaging of the inhibition of the proteasome. The compound is for use in the quantification of proteasomal inhibition, diagnosis and/or prevention and/or treatment of autoimmune diseases, cancer, neurodegenerative diseases, viral infections and/or diseases associated with inflammation. The invention further relates to methods to produce the compounds.

  本发明涉及类似肽的化合物，其作为蛋白酶体抑制剂。这些化合物与发射信号化合物或其前体通过酯（例如磺酯基团）共价连接，用于成像蛋白酶体的抑制。该化合物用于定量蛋白酶体抑制、自身免疫疾病、癌症、神经退行性疾病、病毒感染以及与炎症相关的疾病的诊断、预防和/或治疗。该发明还涉及生产这些化合物的方法。
• PROCESS FOR PRODUCING $g(a)-AMINO-$g(b),$g(d)-DIOL DERIVATIVE
  申请人：Japan Tobacco Inc.

  公开号：EP0523248A1

  公开（公告）日：1993-01-20

  A process for producing compounds represented by general formulae (III) and (IV), which are useful as intermediates for the production of amino acid derivatives which have a renin inhibitory activity and are useful as a hypotensive, stereo-selectively in high yields, which comprises reacting an α-amino aldehyde derivative (I) with a compound (II) in the presence of BF₃ OEt₂ to give an α-amino-β-hydroxy-δ-keto derivative (III) and, if necessary, reducing it into a compound (IV), wherein R¹ represents an amino blocking group; R² represents lower alkyl which may be branched; and R³ represents cyclohexyl or phenyl.

  一种以高产率立体选择性生产通式(III)和(IV)所代表的化合物的工艺，这些化合物可用作生产具有肾素抑制活性并可用作降血压剂的氨基酸衍生物的中间体、其中包括在 BF₃ OEt₂ 存在下，使 α-氨基醛衍生物 (I) 与化合物 (II) 反应，得到 α-氨基-β-羟基-δ-酮衍生物 (III)，必要时还原成化合物 (IV)，其中 R¹ 代表氨基封端基团；R²代表低级烷基，可以是支链烷基；R³代表环己基或苯基。
• US5322963A
  申请人：——

  公开号：US5322963A

  公开（公告）日：1994-06-21