methyl (2S)-2-benzyloxycarboxamido-4-pentenoate | 78553-47-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S)-2-benzyloxycarboxamido-4-pentenoate
• 英文别名: methyl (2S)-2-[N-(benzyloxycarbonyl)amino]pent-4-enoate；L-Allylglycine；(S)-methyl 2-(((benzyloxy)carbonyl)amino)pent-4-enoate；methyl (S)-2-(((benzyloxy)carbonyl)amino)pent-4-enoate；methyl (2S)-2-(N-benzyloxycarbonyl)amino-4-pentenoate；(S)-N-Cbz-allylglycine methyl ester；Methyl (2S)-2-[[(phenylmethoxy)carbonyl]amino]-4-pentenoate；methyl (2S)-2-(phenylmethoxycarbonylamino)pent-4-enoate
• CAS: 78553-47-6
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: RKNNPGXXWNQYKS-LBPRGKRZSA-N

物化性质

• 沸点：
  386.7±42.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-benzyloxycarboxamido-4-pentenoate 在 盐酸 、 lipase AY₃₀ from Candida rugosa 作用下， 以 水 为溶剂， 生成 (2S,4r)-顺式-4-羟基哌啶-2-羧酸
  参考文献：
  名称：

  水解酶在合成环状氨基酸中的用途

  摘要：

  描述了具有所有必要结构特征以使其成为用于药物化学的理想支架的几种环状氨基酸的合成。每个合成过程中的关键步骤是使用水解酶来定义手性中心。为了将这些结构单元详细化为更复杂的分子，使用了结晶和不对称氢化来定义进一步的立体中心。

  DOI：

  10.1016/j.tet.2003.10.116
• 作为产物：
  描述：

  N-苄氧羰酰基-L-丝氨酸甲酯 在 吡啶 、 2,4-滴二甲胺盐 、 sodium iodide 、 锌 作用下， 以 丙酮 为溶剂， 生成 methyl (2S)-2-benzyloxycarboxamido-4-pentenoate
  参考文献：
  名称：

  Synthesis of new 3- and 4-substituted analogues of acyl homoserine lactone quorum sensing autoinducers

  摘要：

  The quorum sensing mechanism in Gram-negative bacteria uses small intercellular signal molecules, N-acyl-homoserine lactones (AHLs), to control transcription of specific genes in relation to population density. In this communication, we describe the parallel synthesis of new AHL analogues, in which substituents have been introduced into the 3- and 4-positions of the lactone ring. These analogues have been screened for their ability to activate and inhibit a Vibrio fischeri LuxI/LuxR-derived quorum sensing reporter system. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00756-9

文献信息

• Alternating Radical Stabilities: A Convergent Route to Terminal and Internal Boronates
  作者：Qi Huang、Jean Michalland、Samir Z. Zard

  DOI：10.1002/anie.201906497

  日期：2019.11.18

  on the boron atom, thus stabilizing or not stabilizing the corresponding adjacent radical, it is possible to control the behavior of α-boronyl xanthates and construct a large variety of terminal or internal boronates in a modular fashion. The remarkable tolerance of polar groups and the ability to introduce quaternary centers are particularly noteworthy features of this process.

  与硼被sp3-杂化的二乙醇胺基硼酸酯[B（DEA）]相比，硼上具有空p轨道的品纳可乐硼酸酯（Bpin）可以稳定相邻的碳原子团。通过将频哪醇或二乙醇胺部分交替地放置在硼原子上，从而稳定或不稳定相应的相邻基团，可以控制α-硼基黄原酸酯的行为，并以模块化的方式构建多种末端或内部的硼酸酯。极性基团的显着耐受性和引入四元中心的能力在此过程中特别值得注意。
• Synthesis and in vitro enzyme activity of peptide derivatives of bacterial cell wall biosynthesis inhibitors
  作者：Russell J. Cox、Helen Jenkins、James A. Schouten、Rosie A. Stentiford、Katrina J. Wareing

  DOI：10.1039/b002701o

  日期：——

  The enzyme diaminopimelate aminotransferase (DAP-AT) is a good potential target for the design of novel antibacterial agents. We have synthesised a series of peptide hydrazines based on the structure of the natural substrate of DAP-AT. These compounds show varied inhibition properties in vitrovs. DAP-AT from E. coli as well as moderate antimicrobial activity vs. E. coli. Examination of the kinetics of inhibition reveals that hydrazine, as well as the substituted hydrazino-peptides, shows two-phase slow-binding inhibition. Possible mechanisms for inhibition are discussed.

  二氨基庚二酸转氨酶（DAP-AT）是一个良好的新型抗菌药物设计潜在靶点。我们基于DAP-AT天然底物的结构，合成了一系列肽酰肼化合物。这些化合物在体外对大肠杆菌来源的DAP-AT表现出不同的抑制性质，并具有中等程度的抗大肠杆菌活性。抑制动力学的研究表明，肽酰肼及其取代物表现出两阶段慢速结合抑制作用。文章还讨论了可能的抑制机制。
• [EN] HYPOPHOSPHOROUS ACID DERIVATIVES HAVING ANTIHYPERALGIC ACTIVITY AND BIOLOGICAL APPLICATIONS THEREOF<br/>[FR] DÉRIVÉS DE L'ACIDE HYPOPHOSPHOREUX AYANT UNE ACTIVITÉ ANTIHYPERALGIQUE ET LEURS APPLICATIONS BIOLOGIQUES
  申请人：UNIV PARIS DESCARTES

  公开号：WO2012156931A1

  公开（公告）日：2012-11-22

  The invention relates to hypophosphorous acid derivatives of formula (I) wherein - X is H or OH, - R represents one or several radicals R1-R5, identical or different, two of R1-R5 optionally occupying the same position on the phenyl group, one to four of R1-R5 being H and the others being selected in the group comprising - 0-(CH2)n-COOH; - S-(CH2)n-COOH; -NH-(CH2)n-COOH; - 0-(CH,R') -COOH; -O- (CH2)n-OH; OR', -R' being a C1 -C3 alkyl radical;-OH; --COOH; halogen, particularly -F, - CI, -Br, -I, -CF3; -OCF3; -N02; -CH=CH-COOH; - -(CH2)n-COOH; O - (CH2)n- P03H2; O - (CF2)n- P03H2; O - (CH2)n- S03H; O - (CH2)n- CONHOH; O - (CH2)n-tetrazol; O - (CH2)n-hydroxyisoxazol - n = 1 to 5, preferably 1-3; said hypophosrous acid derivatives being diastereoisomers or enantiomers.

  该发明涉及式(I)的次磷酸衍生物，其中- X为H或OH，- R代表一个或几个基团R1-R5，相同或不同，R1-R5中的两个可以选择占据苯基上的同一位置，R1-R5中的一到四个为H，其余的选择自-0-(CH2)n-COOH；-S-(CH2)n-COOH；-NH-(CH2)n-COOH；-0-(CH,R')-COOH；-O-(CH2)n-OH；OR'，其中-R'为C1-C3烷基基团；-OH；-COOH；卤素，特别是-F，-Cl，-Br，-I，-CF3；-OCF3；-NO2；-CH=CH-COOH；-(CH2)n-COOH；O-(CH2)n-P03H2；O-(CF2)n-P03H2；O-(CH2)n-S03H；O-(CH2)n-CONHOH；O-(CH2)n-四唑；O-(CH2)n-羟基异噁唑-n=1至5，优选1-3；所述的次磷酸衍生物为对映异构体或对映体。
• Hydroboration–Suzuki cross coupling of unsaturated amino acids; the synthesis of pyrimine derivatives
  作者：Philip N Collier、Andrew D Campbell、Ian Patel、Richard J.K Taylor

  DOI：10.1016/s0040-4020(02)00541-0

  日期：2002.7

  giving a range of new bis-homophenylalanine and related derivatives in good yields (9 examples, 53–64%). One of the Suzuki coupling products has been elaborated to give the N-Cbz-protected natural product pyrimine. The hydroboration–Suzuki coupling of vinylglycine derivatives was also studied but was less efficient than with the allylglycine derivatives: the best results were obtained using disiamylborane·DMS

  用9-BBN对受保护的烯丙甘氨酸进行氢硼化，然后对所得的有机硼烷进行Suzuki交叉偶联，收率很好，得到了一系列新的双-高苯丙氨酸和相关衍生物（9个实例，53-64％）。已开发出一种铃木偶联产品，以提供受N -Cbz保护的天然产品嘧啶。还研究了乙烯基甘氨酸衍生物的硼氢化-Suzuki偶联，但效率不及烯丙基甘氨酸衍生物：使用二酰亚胺基硼烷·DMS作为硼氢化剂可获得最佳结果。
• Divergent Access to Histone Deacetylase Inhibitory Cyclopeptides via a Late-Stage Cyclopropane Ring Cleavage Strategy. Short Synthesis of Chlamydocin
  作者：Gábor Zoltán Elek、Kaur Koppel、Dzmitry M. Zubrytski、Nele Konrad、Ivar Järving、Margus Lopp、Dzmitry G. Kananovich

  DOI：10.1021/acs.orglett.9b03305

  日期：2019.10.18

  The efficacy of the proposed diversity-oriented approach has been validated by short stereoselective synthesis of natural product chlamydocin, containing a challenging-to-install fragment of (2S,9S)-2-amino-8-oxo-9,10-epoxydecanoic acid (Aoe) and a range of its analogues, derivatives of 2-amino-8-oxodecanoic and 2-aminosuberic acids.

  基于通过在通用的多能环丙醇前体中裂解环丙烷环的裂解来安装多个锌结合功能的后期安装，提出了一种访问组蛋白脱乙酰基酶抑制肽的统一的步骤经济策略。通过短立体选择性合成天然产物衣藻多菌素，证实了所提出的面向多样性的方法的功效，该产物含有（2 S，9 S）-2-氨基-8-氧代-9,10-的具有挑战性的安装片段环氧癸酸（Aoe）及其一系列类似物，2-氨基-8-氧十二烷酸和2-氨基丁二酸的衍生物。