(R)-2-氯-3-甲基丁酸 | 84918-96-7

• 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: (R)-2-氯-3-甲基丁酸
• 英文名称: (R)-2-chloro-3-methylbutanoic acid
• 英文别名: (R)-2-Chloro-3-methylbutyric acid；(2R)-2-chloro-3-methylbutanoic acid
• CAS: 84918-96-7
• 化学式: C₅H₉ClO₂
• mdl: MFCD00044962
• 分子量: 136.578
• InChiKey: DDTJFSPKEIAZAM-SCSAIBSYSA-N

物化性质

• 密度：
  1.144 g/mL at 20 °C(lit.)
• 稳定性/保质期：

  如果按照规定使用和储存，则不会发生分解，且没有已知的危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R34
• 海关编码：
  2915900090
• 危险品运输编号：
  UN 3265 8/PG 3
• 储存条件：
  密封，在2°C至-8°C的条件下保存。

反应信息

• 作为反应物：
  描述：

  (R)-2-氯-3-甲基丁酸 在 正丁基锂 、 dimethyl sulfide borane 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.58h， 生成 (S)-1-(4-methoxyphenyl)-3-methylbutan-2-yl methanesulfonate
  参考文献：
  名称：

  Comparative molecular field analysis of fenoterol derivatives interacting with an agonist-stabilized form of the β2-adrenergic receptor

  摘要：

  The beta(2)-adrenergic receptor (beta(2)-AR) agonist [H-3]-(R,R')-methoxyfenoterol was employed as the marker ligand in displacement studies measuring the binding affinities (K-i values) of the stereoisomers of a series of 4'-methoxyfenoterol analogs in which the length of the alkyl substituent at alpha' position was varied from 0 to 3 carbon atoms. The binding affinities of the compounds were additionally determined using the inverse agonist [H-3]-CGP-12177 as the marker ligand and the ability of the compounds to stimulate cAMP accumulation, measured as EC50 values, were determined in HEK293 cells expressing the beta(2)-AR. The data indicate that the highest binding affinities and functional activities were produced by methyl and ethyl substituents at the alpha' position. The results also indicate that the K-i values obtained using [H-3]-(R,R')methoxyfenoterol as the marker ligand modeled the EC50 values obtained from cAMP stimulation better than the data obtained using [H-3]-CGP-12177 as the marker ligand. The data from this study was combined with data from previous studies and processed using the Comparative Molecular Field Analysis approach to produce a CoMFA model reflecting the binding to the beta(2)-AR conformation probed by [H-3]-(R,R')-4'-methoxyfenoterol. The CoMFA model of the agonist-stabilized beta(2)-AR suggests that the binding of the fenoterol analogs to an agonist-stabilized conformation of the beta(2)-AR is governed to a greater extend by steric effects than binding to the [H-3]-CGP-12177-stabilized conformation(s) in which electrostatic interactions play a more predominate role. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.030
• 作为产物：
  描述：

  L-缬氨酸 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 以80%的产率得到(R)-2-氯-3-甲基丁酸
  参考文献：
  名称：

  Comparative molecular field analysis of fenoterol derivatives interacting with an agonist-stabilized form of the β2-adrenergic receptor

  摘要：

  The beta(2)-adrenergic receptor (beta(2)-AR) agonist [H-3]-(R,R')-methoxyfenoterol was employed as the marker ligand in displacement studies measuring the binding affinities (K-i values) of the stereoisomers of a series of 4'-methoxyfenoterol analogs in which the length of the alkyl substituent at alpha' position was varied from 0 to 3 carbon atoms. The binding affinities of the compounds were additionally determined using the inverse agonist [H-3]-CGP-12177 as the marker ligand and the ability of the compounds to stimulate cAMP accumulation, measured as EC50 values, were determined in HEK293 cells expressing the beta(2)-AR. The data indicate that the highest binding affinities and functional activities were produced by methyl and ethyl substituents at the alpha' position. The results also indicate that the K-i values obtained using [H-3]-(R,R')methoxyfenoterol as the marker ligand modeled the EC50 values obtained from cAMP stimulation better than the data obtained using [H-3]-CGP-12177 as the marker ligand. The data from this study was combined with data from previous studies and processed using the Comparative Molecular Field Analysis approach to produce a CoMFA model reflecting the binding to the beta(2)-AR conformation probed by [H-3]-(R,R')-4'-methoxyfenoterol. The CoMFA model of the agonist-stabilized beta(2)-AR suggests that the binding of the fenoterol analogs to an agonist-stabilized conformation of the beta(2)-AR is governed to a greater extend by steric effects than binding to the [H-3]-CGP-12177-stabilized conformation(s) in which electrostatic interactions play a more predominate role. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.030

文献信息

• Asymmetric Synthesis of 2-chloro- and 2-bromo-alkanoic acids by halogenation of α-D-glucofuranose-derived silyl ketene acetals
  作者：P Angibaud、J.L Chaumette、J.R Desmurs、L Duhamel、G Plé、J.Y Valnot、P Duhamel

  DOI：10.1016/0957-4166(95)00251-j

  日期：1995.8

  2-chloro-alkanoic acids 6 and 7 have been obtained the diastereoselective halogenation of chiral silyl ketene acetals 3a-f, and subsequent saponification of the resulting crude esters. Examples characterized by e.e. values up to 95% are reported. The diastereoface selectivity is independent of the silyl ketene acetal configuration.

  光学活性的（S）-2-溴-和2-氯-链烷酸6和7已经获得了手性甲硅烷基烯酮缩醛3a-f的非对映选择性卤化，随后将所得的粗酯皂化。报告了以ee值高达95％为特征的示例。非对映体的选择性与甲硅烷基烯酮缩醛构型无关。
• Synthesis of libraries of peptidomimetic compounds containing a 2-oxopiperazine unit in the main chain
  作者：Sujit Suwal、Thomas Kodadek

  DOI：10.1039/c3ob27476d

  日期：——

  Peptoid libraries have been shown to be a useful source of protein-binding agents. However, simple linear peptoids lack conformational constraints, which may limit their binding affinity for proteins. Here we report facile chemistry for the assembly of 2-oxopiperazine rings into the main chain of peptoid-like oligomers, thus rigidifying the structure. This modified sub-monomer synthesis is suitable for the creation of high quality combinatorial libraries.

  肽类库已被证明是蛋白质结合剂的有用来源。然而，简单的线性肽类缺乏构象约束，这可能限制它们对蛋白质的结合亲和力。我们在这里报告了一种简单的化学方法，可以将2-氧哌嗪环组装到类肽聚合物的主链中，从而增强结构的刚性。这种改进的亚单体合成适合于高质量组合库的创建。
• C,C-coupling with sulfur-stabilized carbanions — 6. Preparation and electrophilic substitution of 1-[3-methyl-2-(2-thiolanylthio)-butyl]piperidine and dethioacetalization of semicyclic dithioacetals,
  作者：C Birk

  DOI：10.1016/0040-4020(96)00757-0

  日期：1996.9.23

  dithioacetals 12 – 15 are converted into the corresponding carbonyl compounds with [bis(trifluoroacetoxy)iodo]benzene (PIFA). Phenyl dichlorophosphate (PDCP) in the presence of sodium iodide and DMF is found to be a reagent for selective cleavage of the exocyclic CS bond. By using DOWEX 50W and paraformaldehyde in acetone/water a cleavage of both acetalic CS bonds is achieved in certain cases.

  通过对映体纯的1-（2-巯基-3-甲基丁基）哌啶（6）从L-缬氨酸获得1- [3-甲基-2-（2-硫代丙氨硫基）丁基]哌啶（8）。通过柱色谱分离非对映异构体，并研究碳负离子8a与亲电试剂的反应。半环二硫缩醛12-15与[双（三氟乙酰氧基）碘]苯（PIFA）转化为相应的羰基化合物。发现在碘化钠和DMF存在下的二氯磷酸苯酯（PDCP）是选择性裂解环外CS键的试剂。在某些情况下，通过在丙酮/水中使用DOWEX 50W和低聚甲醛，可以实现两个缩醛CS键的裂解。
• Di(1‐naphthyl) methanol ester of carboxylic acids for absolute stereochemical determination
  作者：Jun Zhang、Wei Sheng、Hadi Gholami、Tatsuo Nehira、Babak Borhan

  DOI：10.1002/chir.22775

  日期：2018.2

  The absolute stereochemistry of chiral carboxylic acids is determined as a di(1‐naphthyl)methanol ester derivative. Computational scoring of conformations favoring either P or M helicity of the naphthyl groups, capable of exciton‐coupled circular dichroic coupling, leads to a predicted stereochemistry for the derivatized carboxylic acids.

  手性羧酸的绝对立体化学是由二（1-萘基）甲醇酯衍生物确定的。能够进行萘基的P或M螺旋构象的计算评分，能够进行激子偶联的圆二色性偶联，从而可以预测衍生化羧酸的立体化学。
• A Simple Method for the Determination of Enantiomeric Excess and Identity of Chiral Carboxylic Acids
  作者：Leo A. Joyce、Marc S. Maynor、Justin M. Dragna、Gabriella M. da Cruz、Vincent M. Lynch、James W. Canary、Eric V. Anslyn

  DOI：10.1021/ja205775g

  日期：2011.8.31

  The association between an achiral copper(II) host (1) and chiral carboxylate guests was studied using exciton-coupled circular dichroism (ECCD). Enantiomeric complexes were created upon binding of the enantiomers of the carboxylate guests to the host, and the sign of the resultant CD signal allowed for determination of the configuration of the studied guest. The difference in magnitudes and shapes of the CD signals, in conjunction to be determined successfully. A model was created for the host-guest complexes which successfully predicts the sign of the observed CD signal. Further, Taft parameters were used in the model, leading to rationalization of the observed magnitudes of the CD signals. Finally, the enantiomeric excess (ee) of unknown samples of three chiral carboxylic acid guests was determined with an average absolute error of +/- 3.0%.