sec-butyl 2-bromopropionate | 22710-17-4

• 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: sec-butyl 2-bromopropionate
• 英文别名: 2-bromo-propionic acid sec-butyl ester；2-Brom-propionsaeure-sec-butylester；α-Brom-propionsaeure-sek.-butylester；2-Brom-propionsaeure-sek.-butylester；Butan-2-yl 2-bromopropanoate
• CAS: 22710-17-4
• 化学式: C₇H₁₃BrO₂
• 分子量: 209.083
• InChiKey: CPINRHYWYMKYOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  sec-butyl 2-bromopropionate 在 间苯三酚 、 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Inclusion complexes of EMPO derivatives with 2,6-di-O-methyl-β-cyclodextrin: synthesis, NMR and EPR investigations for enhanced superoxide detection

  摘要：

  评估了八种5-烷氧羰基-5-甲基-1-吡咯啉 N-氧化物（EMPO）型氮酮和5,5-二甲基-1-吡咯啉 N-氧化物（DMPO）在含有2,6-二-O-甲基-β-环糊精（DM-β-CD）存在下捕获超氧阴离子自由基的自由基捕获性质。通过1H-NMR滴定确定顺磁性氮酮-DM-β-CD平衡的化学计量和结合常数。然后进行EPR滴定，并使用二维EPR模拟程序进行分析，得到1:1和1:2的化学计量比以及自旋捕获后的氮氧自由基与DM-β-CD的结合常数。氮氧自由基与DM-β-CD的结合比氮酮更强。评估了氮酮捕获超氧的能力、EPR信号强度的增强以及DM-β-CD对L-抗坏血酸钠还原作用的超分子保护。

  DOI：

  10.1039/b606062e
• 作为产物：
  描述：

  2-溴丙酰溴 、 仲丁醇 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 sec-butyl 2-bromopropionate
  参考文献：
  名称：

  Inclusion complexes of EMPO derivatives with 2,6-di-O-methyl-β-cyclodextrin: synthesis, NMR and EPR investigations for enhanced superoxide detection

  摘要：

  评估了八种5-烷氧羰基-5-甲基-1-吡咯啉 N-氧化物（EMPO）型氮酮和5,5-二甲基-1-吡咯啉 N-氧化物（DMPO）在含有2,6-二-O-甲基-β-环糊精（DM-β-CD）存在下捕获超氧阴离子自由基的自由基捕获性质。通过1H-NMR滴定确定顺磁性氮酮-DM-β-CD平衡的化学计量和结合常数。然后进行EPR滴定，并使用二维EPR模拟程序进行分析，得到1:1和1:2的化学计量比以及自旋捕获后的氮氧自由基与DM-β-CD的结合常数。氮氧自由基与DM-β-CD的结合比氮酮更强。评估了氮酮捕获超氧的能力、EPR信号强度的增强以及DM-β-CD对L-抗坏血酸钠还原作用的超分子保护。

  DOI：

  10.1039/b606062e

文献信息

• Effect of Optically Active Ethyl 2-Phthalimidooxypropionate on the Growth of Cress,<i>Lepidium sativum</i>
  作者：Yukinori TAKEKIDA、Momotoshi OKAZAKI、Yoshihiro SHUTO

  DOI：10.1271/bbb.63.1831

  日期：1999.1

  The effects of 2-phthalimidooxyalkanoic acid derivatives on the germination and root-growth of cress were examined. Since 2-phthalimidooxypropionates were most effective, the optically active ethyl esters were prepared. As the result of biological testing, the (S)-(-)-isomer exhibited stronger activity than the (R)-(+)-isomer. This result is contrary to those from commercial herbicides with similar structures, phenoxy- and oxyphenoxy-propionate-type compounds, where the (R)-isomers are generally known to be the active principles.

  研究了2-邻苯二甲酰亚胺氧基烷酸衍生物对水芹萌发和根生长的影响。由于2-邻苯二甲酰亚胺氧基丙酸酯最为有效，因此制备了光学活性的乙酯。生物测试结果显示，(S)-(-)-异构体比(R)-(+)-异构体表现出更强的活性。这一结果与结构类似、属于苯氧基和羟苯氧基丙酸酯类商业除草剂的情况相反，后者通常认为(R)-异构体是活性成分。
• Palladium-Catalyzed Alkynylation of Secondary α-Bromo Carbonyl Compounds via Stille Coupling
  作者：Jun Yong Kang、Brian T. Connell

  DOI：10.1021/jo200939u

  日期：2011.8.19

  A catalytic intermolecular cross-coupling reaction that couples secondary α-bromo carbonyl compounds with alkynylstannanes to form secondary alkynyl carbonyl compounds via palladium catalysis employing the XPhos ligand is described.

  描述了一种催化的分子间交叉偶联反应，该反应将仲α-溴羰基化合物与炔基锡烷酸酯偶联，通过使用XPhos配体的钯催化形成仲炔基羰基化合物。
• Diastereomeric excess upon cleavage and reformation of diastereomeric alkoxyamines
  作者：Gennady Ananchenko、Sylvain Marque、Didier Gigmes、Denis Bertin、Paul Tordo

  DOI：10.1039/b313990e

  日期：——

  DEPN (N-(2-methylpropan-2-yl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-aminoxyl) based alkoxyamines were studied by means of (1)H and (31)P NMR spectroscopy aiming to distinguish the contributions of diastereoselective homolysis and coupling to the total equilibrium diastereomeric distribution. The TEMPO-based compounds reveal no diastereomeric excess while DEPN based compounds show a moderate excess

  通过（1）H和（1）研究了几种基于TEMPO和DEPN（N-（2-甲基丙-2-基）-N-（1-二乙基膦酰基-2,2-二甲基丙基）-氨基二甲苯基）的烷氧基​​胺的热反应。 31）P NMR光谱法，旨在区分非对映选择性均解和偶联对总平衡非对映异构体分布的贡献。基于TEMPO的化合物未显示出非对映异构体过量，而基于DEPN的化合物在均质和偶联后均显示出适度的过量。DEPN-（丙酸酯样）加合物的均相非对映异构偏好不取决于酯基，它主要受β取代基大小的影响。非对映选择性偶联对总重组速率常数k（c）敏感，并且非对映选择性随k（c）的降低而增加。
• PROCESS FOR PRODUCING WINE LACTONE
  申请人：Yagi Kenji

  公开号：US20130030193A1

  公开（公告）日：2013-01-31

  The present invention relates to a method comprising (A) reacting a β-keto ester with a 2-halo ester under basic conditions to obtain a 2-aceto-3-methyl-succinic acid ester; (B) reacting the resulting 2-aceto-3-methyl-succinic acid ester with methyl vinyl ketone under basic conditions, optionally followed by a decarboxylation reaction and hydrolysis, etc., to obtain an α-methyl-γ-keto acid; and (C) reducing the resulting α-methyl-γ-keto acid to obtain wine lactone or a stereoisomer thereof or a mixture thereof. Alternatively, the present invention relates to a method comprising step (A) as recited above; (B) reacting the resulting 2-aceto-3-methyl-succinic acid ester with methyl vinyl ketone under basic conditions, followed by decarboxylation reaction to obtain an α-methyl-γ-keto acid ester; and (E) reducing the resulting α-methyl-γ-keto acid ester in the presence of a ruthenium complex having a specific structure and in the presence of a hydrogen donor to obtain wine lactone or a stereoisomer thereof or a mixture thereof.

  本发明涉及一种方法，包括：（A）在碱性条件下反应β-酮酯和2-卤代酯，以获得2-乙酰基-3-甲基琥珀酸酯；（B）在碱性条件下反应所得的2-乙酰基-3-甲基琥珀酸酯和甲基乙烯酮，随后可选择进行脱羧反应和水解等步骤，以获得α-甲基-γ-酮酸；（C）在还原剂的作用下还原所得的α-甲基-γ-酮酸，以获得酒内酯或其立体异构体或其混合物。另外，本发明还涉及一种方法，包括步骤（A）如上所述；（B）在碱性条件下反应所得的2-乙酰基-3-甲基琥珀酸酯和甲基乙烯酮，随后进行脱羧反应，以获得α-甲基-γ-酮酸酯；（E）在具有特定结构的铑配合物和氢供体的存在下还原所得的α-甲基-γ-酮酸酯，以获得酒内酯或其立体异构体或其混合物。
• A method for resolving optical isomers
  申请人：TORAY INDUSTRIES, INC.

  公开号：EP0970936A1

  公开（公告）日：2000-01-12

  A method for resolving optical isomers, in which a discriminating liquid consisting of an discriminating agent capable of discriminating optical isomers and a diluent is brought into contact with a mixture containing said optical isomers in counter current, to resolve the optical isomers by adsorption separation, distillation separation, absorption separation or membrane separation, and is recovered at an optical isomer content of 5 wt% or less for recycled use is characterized by satisfying one or more of the following conditions: (a) The dielectric constant of the diluent is 30 or less and the viscosity of the discriminating liquid is 0.2 Pa·s or less at the temperature of the resolving operation. (b) The discriminating agent contained has an effect of splitting the 1H or 13C-NMR spectrum peak of the optical isomers when added and the diluent contained has a dielectric constant equal to or lower than the dielectric constant of the measuring solvent at the time of measuring the 1H or 13C-NMR spectrum. (c) The boiling point of at least one compound of the discriminating agent at the pressure of resolving operation is higher than the boiling point of at least one compound of the diluent at the pressure of resolving operation. (d) The boiling point of at least one compound of the diluent at the pressure of resolving operation is higher than the boiling point of the optical isomers to be resolved, at the pressure of resolving operation by 10°C or more. (e) The concentration of the discriminating agent in the discriminating liquid is 10 wt% or more.

  一种分辨光学异构体的方法，在该方法中，由能够分辨光学异构体的分辨剂和稀释剂组成的分辨液与含有所述光学异构体的混合物逆流接触，通过吸附分离、蒸馏分离、吸收分离或膜分离来分辨光学异构体，并以 5 wt% 或更低的光学异构体含量回收光学异构体以供循环使用，其特征在于满足以下一个或多个条件： (a) 在分辨操作温度下，稀释剂的介电常数为 30 或以下，分辨液的粘度为 0.2 Pa-s 或以下。 (b) 所含鉴别剂在加入时具有分裂光学异构体的 1H 或 13C-NMR 光谱峰的效果，所含稀释剂的介电常数等于或低于测量 1H 或 13C-NMR 光谱时测量溶剂的介电常数。 (c) 至少一种鉴别剂化合物在解析操作压力下的沸点高于至少一种稀释剂化合物在解析操作压力下的沸点。 (d) 至少一种稀释剂化合物在解析操作压力下的沸点比待解析光学异构体在解析操作压力下的沸点高 10°C 或以上。 (e) 鉴别液中鉴别剂的浓度为 10 wt%或以上。