(2R)-2-isobutylmalic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (2R)-2-isobutylmalic acid
• 英文别名: (2R)-2-hydroxy-2-(2-methylpropyl)butanedioic acid；(R)-2-hydroxy-2-isobutylsuccinic acid
• 化学式: C₈H₁₄O₅
• 分子量: 190.196
• InChiKey: AOJRRQNPQBDATA-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-butyl 1-(4-β-D-glucopyranosyloxy-benzyl)ester (2R)-2-hydroxy-2-(2-methylpropyl)-butanedioic acid 在 碳酸氢钠 作用下， 反应 2.0h， 以3 mg的产率得到(2R)-2-isobutylmalic acid
  参考文献：
  名称：

  Constituents from the heartwoods of Osmanthus armatus

  摘要：

  A new ester, armatuside (1), along with 13 known compounds (2-14), were obtained from the ethanolic extract of the heartwoods of Osmanthus armatus. The structures of all compounds were deduced using 1D, and 2D NMR spectroscopic methods. The absolute configuration of 1 was deduced by chemical correlation with a known compound. Compounds 2-14 were isolated from the plant for the first time.

  DOI：

  10.1080/14786410802689713

文献信息

• Enantioselective Synthesis of α-Alkylmalates as the Pharmacophoric Group of Several Natural Alkaloids and Glycosides
  作者：Serry A. A. El Bialy、Holger Braun、Lutz F. Tietze

  DOI：10.1002/ejoc.200500065

  日期：2005.7

  A general enantioselective synthesis of α-alkylmalates found in Cephalotaxus and Orchidaceae species is described. This preparation is based upon Seebach’s procedure for the alkylation of D-malic acid with self-regeneration of stereogenic centers. Reaction of the dioxolanone 8a with LiHMDS and allyl halides as well as benzyl bromide gave 10 and 14, respectively, which could be transformed into enantiopure

  描述了在 Cephalotaxus 和 Orchidaceae 物种中发现的 α-烷基苹果酸酯的一般对映选择性合成。这种制备基于 Seebach 的 D-苹果酸烷基化程序，具有立体中心的自我再生。二氧戊环酮 8a 与 LiHMDS 和烯丙基卤化物以及苄基溴的反应分别得到 10 和 14，它们可以转化为对映纯的α-烷基苹果酸酯 13、15、18 和 19。此外，还制备了 20 型对映纯呋喃. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Discovery of glucosyloxybenzyl 2-hydroxy-2-isobutylsuccinates with anti-inflammatory activities from Pleione grandiflora
  作者：Meiting Wu、Xiaoqian Wu、Lijun Zheng、Linjing Zhang、Jiarui Fu、Xiaoqin Zhang、Shasha Wu、Lin Ni

  DOI：10.1016/j.fitote.2021.105062

  日期：2021.11

  Six new glucosyloxybenzyl 2-hydroxy-2-isobutylsuccinates, pleionesides A-F (1–6), along with two known compounds (7, 8) were obtained from the pseudobulbs of Pleione grandiflora (Rolfe) Rolfe. The structures and absolute configurations of new compounds were established by HRESIMS and NMR data, along with acidic hydrolysis and alkaline hydrolysis experiments. Compounds 1–6 were tested for their anti-inflammatory

  从Pleione grandiflora (Rolfe) Rolfe的假鳞茎中获得了六种新的葡糖氧基苄基 2-羟基-2-异丁基琥珀酸酯、pleionesides AF ( 1 – 6 ) 以及两种已知化合物 ( 7 , 8 ) 。新化合物的结构和绝对构型是通过HRESIMS和NMR数据以及酸性水解和碱性水解实验确定的。化合物1 - 6为他们的抗炎活性进行了测试对LPS诱导BV2小胶质细胞。Amoung它们，2，4和5表现出中等活动带IC 50与阳性对照槲皮素相比，槲皮素的 IC 50值为 28.3 μM ，分别为 73.4、32.8 和 57.1 μM。
• Studies on Orchidaceae Alkaloids. XXXVIII. Asymmetric Synthesis of 2-Isobutylmalic Acid and 2-(Cyclohexylmethyl)malic Acid.
  作者：Svante Brandänge、Staffan Josephson、Staffan Vallén、Ulla Rudén、Wolfgang Nimmich

  DOI：10.3891/acta.chem.scand.27-3668

  日期：——
• Glucosyloxybenzyl 2-Isobutylmalates from the Tubers of <i>Gymnadenia </i><i>c</i><i>onopsea</i>
  作者：Toshio Morikawa、Haihui Xie、Hisashi Matsuda、Masayuki Yoshikawa

  DOI：10.1021/np0581115

  日期：2006.6.1

  Seven new glucosyloxybenzyl 2-isobutylmalates, gymnosides I-VII (1-7), were isolated from the tubers of Gymnadenia conopsea. The structures of 1-7 were determined on the basis of chemical and physicochemical evidence.
• Phenanthrenes, 9,10-dihydrophenanthrenes, bibenzyls with their derivatives, and malate or tartrate benzyl ester glucosides from tubers of Cremastra appendiculata
  作者：Yang Wang、Shu-Hong Guan、Yu-Hui Meng、Yi-Bei Zhang、Chun-Ru Cheng、Yang-Yang Shi、Rui-Hong Feng、Feng Zeng、Zhi-Yuan Wu、Jing-Xian Zhang、Min Yang、Xuan Liu、Qing Li、Xiao-Hui Chen、Kai-Shun Bi、De-An Guo

  DOI：10.1016/j.phytochem.2013.06.001

  日期：2013.10

  Eleven previously unknown compounds and 23 known compounds, including 20 phenanthrene or 9,10-dihydrophenanthrene derivatives, five bibenzyls, seven malate or tartrate benzyl ester glucosides, adenosine and gastrodin were isolated from tubers of Cremastra appendiculata. Among the obtained compounds, two are the first isolated dimers with one phenanthrene or bibenzyl unit connected to C-3 of 2,3,4,5-tetrahydro-phenanthro[2,1-b]furan moiety. In addition, 33 of these compounds were evaluated in vitro for their cytotoxic activity against two cancer cell lines. Among the compounds examined, one compound showed moderate cytotoxic activity, while five showed weak cytotoxic activity against the A549 cell line. (C) 2013 Elsevier Ltd. All rights reserved.