α-Formylcapronsaeureethylester | 19361-66-1

• 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: α-Formylcapronsaeureethylester
• 英文别名: Ethyl α-formylhexanoate；ethyl α-formylcaproate；ethyl 2-formylhexanoate；α-Formyl-capronsaeureaethylester；2-Formylhexancarbonsaeureethylester；Aethyl-α-formylhexanoat
• CAS: 19361-66-1
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: BMMQWCLDJPXNMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-Formylcapronsaeureethylester 在 sodium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 sodium acetate 、 sodium cyanoborohydride 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 BnO-bAla(2R-Bu)-Gly(tBu)-NMe2
  参考文献：
  名称：

  Structure–activity relationships of the peptide deformylase inhibitor BB-3497: modification of the methylene spacer and the P1′ side chain

  摘要：

  Structural modifications to the peptide deformylase inhibitor BB-3497 are described. In this paper, we describe the initial SAR around this lead for modifications to the methylene spacer and the P1' side chain. Enzyme inhibition and antibacterial activity data revealed that the optimum distance between the N-formyl hydroxylamine metal binding group and the P1' side chain is one unsubstituted methylene unit. Additionally, lipophilic P1' side chains that closely mimic the methionine residue in the substrate provided compounds with the best microbiological profile. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00532-8
• 作为产物：
  描述：

  正己酸乙酯 、 甲酸乙酯 在 sodium ethanolate 作用下， 生成 α-Formylcapronsaeureethylester
  参考文献：
  名称：

  Structure–activity relationships of the peptide deformylase inhibitor BB-3497: modification of the methylene spacer and the P1′ side chain

  摘要：

  Structural modifications to the peptide deformylase inhibitor BB-3497 are described. In this paper, we describe the initial SAR around this lead for modifications to the methylene spacer and the P1' side chain. Enzyme inhibition and antibacterial activity data revealed that the optimum distance between the N-formyl hydroxylamine metal binding group and the P1' side chain is one unsubstituted methylene unit. Additionally, lipophilic P1' side chains that closely mimic the methionine residue in the substrate provided compounds with the best microbiological profile. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00532-8

文献信息

• Asymmetric Reduction of<i>β</i>-Keto Esters with an Enzyme from Bakers’ Yeast
  作者：Yasushi Kawai、Munekazu Tsujimoto、Shin-ichi Kondo、Kousuke Takanobe、Kaoru Nakamura、Atsuyoshi Ohno

  DOI：10.1246/bcsj.67.524

  日期：1994.2

  Various β-keto esters have been reduced by one of β-keto ester reductases isolated from bakers’ yeast. The corresponding β-hydroxy esters have been obtained in excellent enantiomeric and diastereomeric excesses, respectively. It has also been elucidated that the reductase recognizes the stereochemistry not only at the β-carbon but also at the α-carbon affording one of the four possible diastereoisomers

  各种 β-酮酯已被从面包酵母中分离出的一种 β-酮酯还原酶还原。相应的β-羟基酯分别以极好的对映体和非对映体过量获得。还阐明了还原酶不仅识别 β-碳上的立体化学，而且识别 α-碳上的立体化学，主要提供 α-取代的 β-羟基酯的四种可能的非对映异构体之一。立体选择性非常好，化学收率中等至良好。
• Stereochemical Control in Microbial Reduction. XXIII. Thermal Treatment of Bakers’ Yeast for Controlling the Stereoselectivity of Reductions
  作者：Yasushi Kawai、Shin-ichi Kondo、Munekazu Tsujimoto、Kaoru Nakamura、Atsuyoshi Ohno

  DOI：10.1246/bcsj.67.2244

  日期：1994.8

  diastereoselectivity in a bakers’ yeast reduction of various alkyl 2-alkyl-3-oxoalkanoates can be controlled by a thermal treatment of the yeast in the presence of methyl vinyl ketone. Pretreated bakers’ yeast gives the corresponding (2R,3S)-hydroxy esters selectively. Two β-keto ester reductases, named L-enzyme-1 and L-enzyme-2, are actual reductants of intact bakers’ yeast reduction. The thermal stability

  面包师酵母还原各种 2-烷基-3-氧代链烷酸烷基酯的非对映选择性可以通过在甲基乙烯基酮存在下对酵母进行热处理来控制。预处理的面包酵母选择性地产生相应的 (2R,3S)-羟基酯。两种 β-酮酯还原酶，称为 L-酶-1 和 L-酶-2，是完整面包酵母还原的实际还原剂。纯化酶的热稳定性和抑制常数可以决定预处理面包酵母减少的立体化学结果。
• Synthese und H2-antihistaminische Wirksamkeit von 2-Amidino-1,2-dihydro-3H-pyrazol-3-onen
  作者：Kurt Wegner

  DOI：10.1002/ardp.19833160103

  日期：——

  Es wird über die Synthese und H2‐antihistaminische Wirksamkeit von 2‐Amidino‐1,2‐dihydro‐3H‐pyrazol‐3‐onen berichtet.

  报道了 2-脒基-1,2-二氢-3H-吡唑-3-酮的合成和 H2-抗组胺活性。
• Reactions of Vinyloxyboranes with Carbonyl Compounds, Nitriles, and Formates
  作者：Masayoshi Muraki、Katsuhiko Inomata、Teruaki Mukaiyama

  DOI：10.1246/bcsj.48.3200

  日期：1975.11

  be formed in reaction of phenyl di-n-butylthioboronite (II) with methyl vinyl ketone. In order to explore its utilization in organic synthesis, the reactivity of Id and other known vinyloxyboranes was variously examined. Id and Ie gave β-hydroxyketones (IVa–c, Va–d) in fairly good yields when they were allowed to react with carbonyl compounds. The reaction of Ia′ and Ib with nitriles, followed by hydrolysis

  发现在苯基二正丁基硫代硼酸盐 (II) 与甲基乙烯基酮反应中形成了一种新的乙烯基氧基硼烷衍生物 Id。为了探索其在有机合成中的应用，对 Id 和其他已知乙烯基氧基硼烷的反应性进行了各种检查。当它们与羰基化合物反应时，Id 和 Ie 以相当好的产率得到 β-羟基酮（IVa-c，Va-d）。Ia'和Ib与腈反应，然后水解，分别得到β-亚氨基硫酸酯（VIa-c）和β-酮酯（VIIa-d）。还发现硼烷(Ib)在室温下与甲酸酯或甲酰胺反应得到α-甲酰基己酸乙酯。
• Water/n‐Octanol Partition Coefficients of 1,2‐Dithiole‐3‐thiones
  作者：M. Bona、P. Boudeville、O. Zekri、M.O. Christen、J.L. Burgot

  DOI：10.1002/jps.2600840914

  日期：1995.9

  Water/n-octanol partition coefficients (log P) for 33 1,2-dithiole-3-thiones and for 18 1,2-dithiol-3-ones were determined by RP-HPLC measurement of the concentration of the solute in aqueous solution after equilibrium. Depending on the nature of the substituents (alkyl or aryl) and their position(s) (4,5, or both) on the dithiole nucleus, some peculiar behaviors were revealed. Therefore, different

  通过RP-HPLC测定水溶液中溶质的浓度，确定了33个1,2-二硫代-3-硫酮和18个1,2-二硫代-3-酮的水/正辛醇分配系数（log P）平衡后。根据取代基（烷基或芳基）的性质及其在二硫醇核上的位置（4,5或两者），揭示了一些特殊的行为。因此，推断出包含1，2-二硫代-3-硫酮核的不同片段常数，以便在补充工作中先验地计算新的二硫代硫酮和二硫酮的log P值。