methyl (E,4S)-4-((tert-butoxycarbonyl)amino)-6-methylhept-2-enoate | 114423-50-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (E,4S)-4-((tert-butoxycarbonyl)amino)-6-methylhept-2-enoate
• 英文别名: methyl (2E,4S)-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-6-methyl-2-heptenoate；methyl (E,4S)-6-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]hept-2-enoate
• CAS: 114423-50-6
• 化学式: C₁₄H₂₅NO₄
• 分子量: 271.357
• InChiKey: OSYXEAIPHIBUPE-WSKFYRRCSA-N

物化性质

• 沸点：
  364.5±35.0 °C(Predicted)
• 密度：
  1.005±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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 (E,4S)-4-((tert-butoxycarbonyl)amino)-6-methylhept-2-enoate 在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 (E)-(S)-4-(Benzhydrylidene-amino)-6-methyl-hept-2-enoic acid methyl ester
  参考文献：
  名称：

  γ-氨基-α，β-不饱和酯经由其芳基酮亚胺衍生物的立体选择性二羟基化反应。

  摘要：

  （E）-γ-氨基-α，β-不饱和酯的芳基酮亚胺衍生物的OsO4催化的二羟基化反应产生的反选择性范围为6.7：1至19：1，而与（（ Z）-γ-氨基-α，β-不饱和酯（5.4：1至> 100：1）。

  DOI：

  10.1039/b414846k
• 作为产物：
  描述：

  N-叔丁氧羰基-L-亮氨醇 在 碳酸氢钠 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl 、 sodium hypochlorite 、 sodium bromide 作用下， 以 四氢呋喃 、 乙酸乙酯 、 甲苯 为溶剂， 反应 2.25h， 生成 methyl (E,4S)-4-((tert-butoxycarbonyl)amino)-6-methylhept-2-enoate
  参考文献：
  名称：

  Inhibition of Group IVA Cytosolic Phospholipase A₂ by Novel 2-Oxoamides in Vitro, in Cells, and in Vivo

  摘要：

  The Group IVA cytosolic phospholipase A(2) (GIVA PLA(2)) is a particularly attractive target for drug development because it is the rate-limiting provider of proinflammatory mediators. We previously reported the discovery of novel 2-oxoamides that inhibit GIVA PLA(2) [Kokotos, G.; et al. J. Med. Chem. 2002, 45, 2891-2893]. In the present work, we have further explored this class of inhibitors and found that the 2-oxoamide functionality is more potent when it contains a long 2-oxoacyl residue and a free carboxy group. Long-chain 2-oxoamides based on gamma-aminobutyric acid and gamma-norleucine are potent inhibitors of GIVA PLA(2). Such inhibitors act through a fast and reversible mode of inhibition in vitro, are able to block the production of arachidonic acid and prostaglandin E-2 in cells, and demonstrate potent in vivo antiinflammatory and analgesic activity.

  DOI：

  10.1021/jm030485c

文献信息

• Burgess Reagent Facilitated Alcohol Oxidations in DMSO
  作者：Prakash R. Sultane、Christopher W. Bielawski

  DOI：10.1021/acs.joc.6b02629

  日期：2017.1.20

  Burgess reagent ([methoxycarbonylsulfamoyl]triethylammonium hydroxide) has historically found utility as a dehydrating agent. Herein we show that, in the presence of dimethyl sulfoxide, the Burgess reagent efficiently and rapidly facilitates the oxidation of a broad range of primary and secondary alcohols to their corresponding aldehydes and ketones in excellent yields and under mild conditions, and can

  历史上已经发现Burgess试剂（[[甲氧基羰基氨磺酰基]三乙基氢氧化铵]可用作脱水剂。本文中，我们表明，在二甲亚砜的存在下，伯吉斯试剂可以高效，迅速地促进各种伯醇和仲醇氧化成其相应的醛和酮，且收率极高，且温度适中，并且可以与其他方法结合使用。转化（例如Wittig烯烃化）。提出了一种类似于针对Pfitzner-Moffatt和Swern氧化所描述的机理。
• [EN] CATHEPSIN C INHIBITORS<br/>[FR] INHIBITEURS DE LA CATHEPSINE C
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2012109415A1

  公开（公告）日：2012-08-16

  Disclosed are 4-amino-2-butenamides of Formula (I) having pharmacological activity, pharmaceutical compositions containing them, and methods for the treatment of diseases mediated by the cathepsin C enzyme such as chronic obstructive pulmonary disease.

  本文披露了具有药理活性的式（I）的4-氨基-2-丁烯酰胺，含有它们的药物组合物，以及用于治疗由cathepsin C酶介导的疾病的方法，如慢性阻塞性肺疾病。
• ?-Peptides Forming More Stable Secondary Structures than ?-Peptides: Synthesis and helical NMR-solution structure of the ?-hexapeptide analog of H-(Val-Ala-Leu)2-OH
  作者：Tobias Hintermann、Karl Gademann、Bernhard Jaun、Dieter Seebach

  DOI：10.1002/hlca.19980810514

  日期：——

  acid, and (R)-4-amino-6-methylheptanoic acid. The precursors were prepared either by double Arndt-Eistert homologation of the protected amino acids Boc-Val-OH, Boc-Ala-OH, and Boc-Leu-OH (Schemes 1 and 2), or by the superior route involving olefination/hydrogenation of the corresponding aldehydes (Boc-valinal, Boc-alaninal, and Boc-leucinal; Scheme 3). Conventional peptide-coupling methodology (EDC/HOBt)

  为了与相应的α-和β-六肽H-（Val-Ala-Leu）2 -OH（A）和H-（β-HVal-β-HAla-β-HLeu）2 -OH（B）进行比较，我们现在准备了由手性相似的（S）-4-氨基丁酸，（R）-4-氨基-5-甲基己酸和（R）-4-氨基-6-甲基庚酸构建的相应的γ-六肽1。通过对受保护氨基酸Boc-Val-OH，Boc-Ala-OH和Boc-Leu-OH进行双重Arndt - Eistert同源性制备前体（方案1和2），或通过涉及相应醛的烯化/加氢的高级途径（Boc-戊醛，Boc-丙氨酸和Boc-亮氨酸；方案3）。常规肽偶合方法（EDC / HOBT）提供的γ-六肽1（通过中间γ-二-和γ-三肽衍生物9 - 11）。在（D 5）吡啶和CD 3 OH溶液（COSY，TOCSY，HSQC，HMBC，ROESY）中进行的NMR测量分析表明，γ-六肽1采用右旋螺旋结构（（P）-2.6 1
• Intramolecular Nucleophilic Epoxidation of γ-Amino-α,β-Unsaturated Esters with an<i>N</i>-Hydroperoxymethyl Group
  作者：Young Gyu Kim、Dongwon Yoo、Hyeonjeong Kim

  DOI：10.1055/s-2005-871558

  日期：——

  Intramolecular nucleophilic epoxidation reactions of γ-amino-α,β-unsaturated esters have been studied for the first time with a hydroperoxymethyl group attached to the nitrogen atom. The epoxidation was fast under mild basic conditions and highly anti selective (>20:1) when the alkyl group is small.

  首次研究了γ-氨基-α,β-不饱和酯的分子内亲核环氧化反应，其中氢过氧甲基与氮原子相连。环氧化在弱碱性条件下快速，当烷基较小时具有高抗选择性（>20:1）。
• CATHEPSIN C INHIBITORS
  申请人：Anderson Niall

  公开号：US20120142668A1

  公开（公告）日：2012-06-07

  Disclosed are 4-amino-2-butenamides of Formula (I) having pharmacological activity, pharmaceutical compositions containing them, and methods for the treatment of diseases mediated by the cathepsin C enzyme such as chronic obstructive pulmonary disease.

  揭示了式（I）的4-氨基-2-丁烯酰胺具有药理活性，包含它们的制药组合物，以及治疗由cathepsin C酶介导的疾病（如慢性阻塞性肺疾病）的方法。