庚酸酯 | 7563-37-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 庚酸酯
• 中文别名: O-(2-氨基乙基)-L-丝氨酸
• 英文名称: heptanoate
• 英文别名: heptanoic acid; deprotonated form；Heptanoat
• CAS: 7563-37-3
• 化学式: C₇H₁₃O₂
• 分子量: 129.179
• InChiKey: MNWFXJYAOYHMED-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  40.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-[2-(3-acetoxy-octyl)-4-oxo-thiazolidin-3-yl]-heptanoic acid methyl ester 、 庚酸酯 在 silica gel 作用下， 生成 7-[2-(3(S)-hydroxyoctyl)-4-oxo-3-thiazolidinyl]heptanoic acid
  参考文献：
  名称：

  Certain thiazolidine compounds

  摘要：

  本发明涉及新型8-aza-9-oxo-11-thia、-11-oxothia和-11-dioxothia-prostanoic酸化合物、盐和衍生物的制备方法。这些化合物具有类前列腺素的生物活性，特别适用于肾血管扩张剂、治疗某些自身免疫性疾病和预防血栓形成。

  公开号：

  US04059587A1
• 作为产物：
  描述：

  庚酸 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.42h， 生成 庚酸酯
  参考文献：
  名称：

  Lactones. 2. Enthalpies of hydrolysis, reduction, and formation of the C4-C13 monocyclic lactones. Strain energies and conformations

  摘要：

  The enthalpies of hydrolysis of the monocyclic lactones from gamma-butyrolactone to tridecanolactone were determined calorimetrically, and the acyclic ethyl esters having the same number of atoms were studied in the same fashion. The enthalpies of reduction of the lactones to the corresponding alpha,omega-alkanediols with lithium triethylborohydride also were determined. The enthalpies of formation of the lactones and the ethyl esters were derived from these data. They were converted to values for the gas phase by measuring the enthalpies of vaporization of ethyl esters and of lactones. In the cases of gamma-butyrolactone and delta-valerolactone, the enthalpies of formation were in good accord with the previously reported values determined via combustion calorimetry. The strain energies of the lactones were obtained via isodesmic reactions. Valerolactone had a strain energy of 11 kcal/mol, and the largest strain energy was found with octanolactone (13 kcal/mol). The conformations of gamma-butyrolactone and delta-valerolactone were studied via MP2/6-31G* geometry optimizations, and the conformations of the other lactones were studied with use of the molecular mechanics program MM3. The energies of the lactones estimated via molecular mechanics were compared with the experimental results.

  DOI：

  10.1021/ja00020a036
• 作为试剂：
  描述：

  乙酰乙酸乙酯 、 1-溴-5-氯戊烷 、 potassium carbonate 在 正庚烷 、 庚酸酯 作用下， 以 正庚烷 为溶剂， 反应 14.0h， 以to give a solution (347 g) of crude ethyl 7-chloro-2-(1-oxoethyl)heptanoate [II-1] in n-heptane (content of the heptanoate的产率得到7-chloro(1-oxoethyl)heptanoic acid ethyl ester
  参考文献：
  名称：

  Process for preparing haloketo acid derivatives

  摘要：

  制备卤代酮酸衍生物的过程[I]：其中R是H或C.sub.1-6烷基，X是氯或溴，包括将β-氧代酸酯[II]与亚硝化试剂[IV]反应：其中R.sup.4是H，烷基，卤素或SO.sub.3 H，以得到7-卤代-2-羟基氨基庚酸酯[III]，其中R.sup.1和X与上述相同，然后再将该产物与醛或酮反应；以及制备该中间体的过程。所述卤代酮酸衍生物可用作合成西司他丁的中间体，西司他丁可用作药物，特别是作为脱氢肽酶抑制剂。

  公开号：

  US05268501A1

文献信息

• CYCLODEXTRIN-CATALYZED HYDROLYSIS OF ESTERS BEARING A HYDROPHOBIC TAIL
  作者：Akihiko Ueno、Iwao Suzuki、Yoshihiro Hino、Atsuko Suzuki、Tetsuo Osa

  DOI：10.1246/cl.1985.159

  日期：1985.2.5

  γ-Cyclodextrin-catalyzed hydrolysis of p-nitrophenyl esters bearing a long alkyl chain proceeded with larger rate acceleration than those with a short alkyl chain. Such rate acceleration behavior was not observed with β-cyclodextrin. The results suggest that the esters with a long alkyl chain take a folded structure (Type A) in the γ-cyclodextrin cavity.

  与短烷基链的对硝基苯酯相比，γ-环糊精催化的长烷基链对硝基苯酯水解的速率加速度更大。而在β-环糊精中则没有观察到这种速率加速行为。结果表明，具有长烷基链的酯类在 γ-环糊精空腔中具有折叠结构（A 型）。
• Substituted 3-amino chromans
  申请人：The Upjohn Company

  公开号：US05306830A1

  公开（公告）日：1994-04-26

  The present invention is directed to novel chromane derivatives substituted in the 3-position by a substituted amino moiety and substituted on the aromatic ring with one or two substituents. The novel chromane derivatives have useful CNS properties. ##STR1##

  本发明涉及一种新型的基于色酮的衍生物，其在3位被取代的氨基基团取代，且在芳环上被一个或两个取代基所取代。这些新型的色酮衍生物具有有用的中枢神经系统特性。##STR1##
• Jasmonates meet fatty acids: functional analysis of a new acyl-coenzyme A synthetase family from Arabidopsis thaliana
  作者：Lucie Kienow、Katja Schneider、Michael Bartsch、Hans-Peter Stuible、Hua Weng、Otto Miersch、Claus Wasternack、Erich Kombrink

  DOI：10.1093/jxb/erm325

  日期：2008.2

  Arabidopsis thaliana contains a large number of genes encoding carboxylic acid-activating enzymes, including long-chain fatty acyl-CoA synthetase (LACS), 4-coumarate:CoA ligases (4CL), and proteins closely related to 4CLs with unknown activities. The function of these 4CL-like proteins was systematically explored by applying an extensive substrate screen, and it was uncovered that activation of fatty acids is the common feature of all active members of this protein family, thereby defining a new group of fatty acyl-CoA synthetase, which is distinct from the known LACS family. Significantly, four family members also displayed activity towards different biosynthetic precursors of jasmonic acid (JA), including 12-oxo-phytodienoic acid (OPDA), dinor-OPDA, 3-oxo-2(2′-[Z]-pentenyl)cyclopentane-1-octanoic acid (OPC-8), and OPC-6. Detailed analysis of in vitro properties uncovered significant differences in substrate specificity for individual enzymes, but only one protein (At1g20510) showed OPC-8:CoA ligase activity. Its in vivo function was analysed by transcript and jasmonate profiling of Arabidopsis insertion mutants for the gene. OPC-8:CoA ligase expression was activated in response to wounding or infection in the wild type but was undetectable in the mutants, which also exhibited OPC-8 accumulation and reduced levels of JA. In addition, the developmental, tissue- and cell-type specific expression pattern of the gene, and regulatory properties of its promoter were monitored by analysing promoter::GUS reporter lines. Collectively, the results demonstrate that OPC-8:CoA ligase catalyses an essential step in JA biosynthesis by initiating the β-oxidative chain shortening of the carboxylic acid side chain of its precursors, and, in accordance with this function, the protein is localized in peroxisomes.

  拟南芥含有大量编码羧酸活化酶的基因，包括长链脂肪酰基-CoA 合成酶（LACS）、4-香豆酸：CoA 连接酶（4CL）以及与 4CL 密切相关但活性未知的蛋白。通过广泛的底物筛选，系统地探索了这些 4CL 类蛋白质的功能，发现脂肪酸的活化是该蛋白家族所有活性成员的共同特征，从而定义了一组新的脂肪酰基-CoA 合成酶，与已知的 LACS 家族不同。值得注意的是，四个家族成员还对茉莉酸（JA）的不同生物合成前体表现出活性，包括 12-氧代-2-(2′-[Z]-戊烯基)环戊烷-1-辛酸（OPC-8）和 OPC-6。对体外特性的详细分析发现，各酶的底物特异性存在显著差异，但只有一种蛋白质（At1g20510）显示出 OPC-8:CoA 连接酶活性。通过对拟南芥基因插入突变体进行转录本和茉莉酸酯分析，分析了其体内功能。在野生型中，OPC-8:CoA 连接酶的表达在受伤或感染时被激活，但在突变体中却检测不到，突变体也表现出 OPC-8 的积累和 JA 水平的降低。此外，还通过分析启动子：：GUS 报告基因系监测了该基因的发育、组织和细胞类型特异性表达模式及其启动子的调控特性。总之，研究结果表明，OPC-8:CoA 连接酶通过启动其前体羧酸侧链的 β-氧化链缩短作用，催化了 JA 生物合成过程中的一个重要步骤。
• Identification of Key Residues for Enzymatic Carboxylate Reduction
  作者：Holly Stolterfoht、Georg Steinkellner、Daniel Schwendenwein、Tea Pavkov-Keller、Karl Gruber、Margit Winkler

  DOI：10.3389/fmicb.2018.00250

  日期：——

  Little is known about the structure of CARs and their catalytically important amino acid residues. The identification of key residues for carboxylate reduction provides a starting point to gain deeper understanding of enzymatic carboxylate reduction. A multiple sequence alignment of CARs with confirmed activity recently identified in our lab and from the literature revealed a fingerprint of conserved

  羧酸还原酶（CARs，EC 1.2.1.30）从其相应的羧酸中以高选择性生成醛。关于CAR的结构及其催化重要的氨基酸残基知之甚少。鉴定用于羧酸盐还原的关键残基为深入了解酶促羧酸盐还原提供了一个起点。最近在我们的实验室中从文献中鉴定出具有确定活性的CAR的多序列比对，揭示了保守氨基酸的指纹。我们通过这些残基的多个序列比对和突变替换研究了保守残基的功能。在这项研究中，研究了Neurospora crassa CAR的单部位丙氨酸变体，以确定保守残基对功能的贡献，酶的表达性或稳定性。通过在体内和体外分析变体的酶活性来研究氨基酸置换的作用。在分子建模的支持下，我们解释了这些残基中的五个对于催化活性或底物和共底物结合至关重要。我们鉴定出对CAR活性具有显着影响的氨基酸残基。用Ala替代His 237，Glu 433，Ser 595，Tyr 844和Lys 848废除了CAR活性，表明它们在减少酸中的
• Contrasting behaviors of the cleavage of aryl alkanoates by .alpha.- and .beta.-cyclodextrins in basic aqueous solution
  作者：Oswald S. Tee、Xian Xian Du

  DOI：10.1021/jo00243a055

  日期：1988.4

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