methyl 2,4,5-tribenzamido-4-pentenoate | 6298-09-5

• 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: methyl 2,4,5-tribenzamido-4-pentenoate
• 英文别名: (S)-2,4,5ξ-tris-benzoylamino-pent-4-enoic acid methyl ester；(S)-2,4,5ξ-Tris-benzoylamino-pent-4-ensaeure-methylester；L-1.2.4-Tris-benzamino-penten-(1)-saeure-(5)-methylester；(S)-2,4,5-Tris(benzoylamino)-4-pentenoic Acid Methyl Ester；methyl (2S)-2,4,5-tribenzamidopent-4-enoate
• CAS: 6298-09-5；66675-21-6；78420-24-3；78420-23-2
• 化学式: C₂₇H₂₅N₃O₅
• 分子量: 471.513
• InChiKey: AACGMMSOMRBWNU-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  methyl 2,4,5-tribenzamido-4-pentenoate 在 盐酸 作用下， 以 甲醇 为溶剂， 以79%的产率得到N2,N5-二苯甲酰-4-氧代-L-鸟氨酸甲酯
  参考文献：
  名称：

  Cysteine as a sustainable sulfur reagent for the protecting-group-free synthesis of sulfur-containing amino acids: biomimetic synthesis of l-ergothioneine in water

  摘要：

  生物质来源的半胱氨酸被用作可持续的硫源，用于合成稀有的含硫氨基酸，如可能是一种新维生素的L-厄替奥宁（L-ergothioneine）以及各种L-或D-2-硫组氨酸化合物。该简单的一锅两步水相反应程序的关键是通过溴诱导选择性引入半胱氨酸，然后在硫醇存在下进行新型热裂解反应，这是一种比危险红磷更安全的替代方法。除了避免有害的硫试剂外，这种新的无保护基团的方法大大减少了总步骤数，相较于已有的程序。主要缺点，即在水中处理作为活化和氧化试剂的液溴，已通过评估四种替代方法（使用原位生成溴或次溴酸）进行解决，并描述了初步令人鼓舞的结果。

  DOI：

  10.1039/c2gc35367a
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 水 、 sodium carbonate 作用下， 生成 methyl 2,4,5-tribenzamido-4-pentenoate
  参考文献：
  名称：

  CCCXLII.—1-2-2-巯基组氨酸的合成

  摘要：

  DOI：

  10.1039/jr9300002586

文献信息

• Synthesis of Four Stereoisomers of γ-Hydroxyarginine<i>via</i>the Corresponding Isomers of γ-Hydroxyornithine
  作者：Koichi Mizusaki、Satoru Makisumi

  DOI：10.1246/bcsj.54.470

  日期：1981.2

  estimated to be 68% erythro and 32% threo isomers and that of the product from D-histidine 65% erythro and 35% threo isomers by automatic amino acid analysis after conversion of the basic amino acids into neutral Nδ-acetyl derivatives. The diastereoisomers of each γ-hydroxyorni thine were separated by chromatography on a Dowex 50 column, four optically active isomers being isolated as their hydrochlorides

  非对映异构 γ-羟基-L-和 D-鸟氨酸是通过用硼氢化钠还原由 L-和 D-组氨酸合成的相应 γ-氧代鸟氨酸来制备的。通过碱性转化后的自动氨基酸分析，估计从 L-组氨酸获得的产物的异构体组成为 68% 赤型和 32% 苏型异构体，而 D-组氨酸产品的异构体组成为 65% 赤型和 35% 苏型异构体氨基酸转化为中性 Nδ-乙酰基衍生物。每种 γ-羟基鸟氨酸的非对映异构体在 Dowex 50 柱上通过色谱法分离，四种旋光异构体被分离为结晶状态的盐酸盐。这些异构体与 1-脒基-3 的胍基化，5-二甲基吡唑硝酸盐 (ADPN) 得到 γ-羟基精氨酸的相应旋光异构体，其作为结晶盐酸盐被分离。赤型-γ-羟基-L-精氨酸盐酸盐显示出与γ-羟基精氨酸的天然产物非常接近的比旋光度。
• Heath et al., Journal of the Chemical Society, 1951, p. 2215
  作者：Heath et al.

  DOI：——

  日期：——
• The Conversion of L-Histidine into Hydroxy- and Allohydroxy-proline via erythro- and threo-γ-Hydroxy-L-ornithine^1,2
  作者：Bernhard Witkop、Theodore Beiler

  DOI：10.1021/ja01593a066

  日期：1956.6
• Dose-response relationships for edrophonium and neostigmine antagonism of atracurium and cisatracurium- induced neuromuscular block
  作者：Mohamed Naguib、Waleed Riad

  DOI：10.1007/bf03027958

  日期：2000.11

  Purpose: To study the dose-response relationships for neostigmine and edrophonium during antagonism of neuromuscular block induced by atracurium and cisatracurium.Methods: One hundred and twenty eight, ASA group 1 or 2 adults were given either 0.5 mg.kg(-1) atracurium or 0.1 mg.kg(-1) cisatracurium during fentanyl-thiopental-nitrous oxide-isoflurane anesthesia. The neuromuscular block was measured by an acceleration-responsive transducer. Responses were defined in terms of percent depression in the first twitch (T1) and train-of-four (TOF) response. When spontaneous recovery of first twitch height reached 10% of its initial control value, edrophonium (0, 1, 0.2, 0,4, or 1 mg.kg(-1)) or neostigmine (0.005, 0.01, 0.02, or 0.05 mg.kg(-1)) was administered by random allocation, Neuromuscular function in another sixteen subjects was allowed to recover spontaneouslyResults: At five minutes, unlike edrophonium, neostigmine was equally effective against atracurium and cisatracurium with respect to TI recovery. The neostigmine TI-ED50 was 10.3 +/- 1.06 (SEM) mug.kg(-1) after atracurium and 11.2 +/- 1.06) mug.kg(-1) after cisatracurium. The edrophonium ED50 was 157 +/- 1.07 mug.kg(-1) with atracurium and 47.4 +/- 1.07 mug.kg(-1) with cisatracurium, giving a neostigmine:edrophonium potency ratios of 15.2 +/- 1.7 and 4.2 +/- 0.41 (P < 0.001)for atracurium and cisatracurium, respectively At 10 min neostigmine was 13 +/- 1.4 times as potent as edrophonium for achieving 50% TOF recovery after atracurium paralysis. After cisatracurium the potency ratio was 11.8 +/- 1.3 (NS).Conclusions: Although there were differences at five minutes, neostigmine:edrophonium potency ratios at 10 min, were similar in both relaxants studied.