2S-Hydroxy-succinic diisopropyl ester | 58110-67-1

• 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: 2S-Hydroxy-succinic diisopropyl ester
• 英文别名: di-i-propyl 2-hydroxybutandioate；diisopropyl malate；(S)-diisopropyl malate；D-(+)-diisopropyl malate；diiso-propyl malate；dipropan-2-yl 2-hydroxybutanedioate
• CAS: 58110-67-1
• 化学式: C₁₀H₁₈O₅
• mdl: MFCD24390202
• 分子量: 218.25
• InChiKey: XYVHRFVONMVDGK-UHFFFAOYSA-N

物化性质

• 沸点：
  301.2±22.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苄基氯甲基醚 、 2S-Hydroxy-succinic diisopropyl ester 在 N,N-二甲基丙烯基脲 、 lithium diisopropyl amide 作用下， 生成
  参考文献：
  名称：

  James, Gwyn D.; Mills, Stuart D.; Pattenden, Gerald, Journal of the Chemical Society. Perkin transactions I, 1993, # 21, p. 2581 - 2584

  摘要：

  DOI：
• 作为产物：
  描述：

  苹果酸 、 alkaline earth salt of/the/ methylsulfuric acid 反应 2.0h， 以73%的产率得到2S-Hydroxy-succinic diisopropyl ester
  参考文献：
  名称：

  Esterification in dry Media Using Ferric Perchlorate Adsorbed on Silica Gel

  摘要：

  Adsorption of Fe(ClO4)(3)(H2O)(6) onto chromatographic grade silica gel in the presence of alcohol (to be used for esterification) produces a supported reagent, Fe(ClO4)(3)(ROH)(6)/SiO2. This reagent, has been found effective for the rapid and high yield of esters, on grinding in the presence of carboxylic acids using pestle and mortar in the solid state.

  DOI：

  10.1080/00397919808004858

文献信息

• [EN] METALLOPROTEINASE INHIBITORS<br/>[FR] INHIBITEURS DE METALLOPROTEINASES
  申请人：BRITISH BIOTECH PHARM

  公开号：WO2004101537A1

  公开（公告）日：2004-11-25

  Compounds formula (IA) or (IB); wherein W represents HO(C=0)-, HONH(C=0)- or H(C=O)N(OH)-; X represents -O- or -S-; and R1, R2, and R3 are as defined in the description and claims, are inhibitors of matrix metalloproteinases, in particular MMP9 and/or MMP12.

  化合物的结构式（IA）或（IB）；其中，W代表HO(C=0)-，HONH(C=0)-或H(C=0)N(OH)-；X代表-O-或-S-；而R1、R2和R3如描述和权利要求中所定义的，是基质金属蛋白酶，特别是MMP9和/或MMP12的抑制剂。
• Process for the stereoselective transformation of a diol to an alcohol
  申请人：Sepracor, Inc.

  公开号：US05189200A1

  公开（公告）日：1993-02-23

  An efficient and commerically-viable method for the stereoselective transformation of a diol to an alcohol is disclosed. The present method is particularly well-suited for the preparation of the unnatural D-isomer of malic acid or its derivatives from the abundant naturally occurring L-tartaric acid or derivatives thereof.

  一种高效且商业可行的立体选择性将二醇转化为醇的方法被披露。该方法特别适用于从丰富的天然存在的L-酒石酸或其衍生物制备人工D-异构体的苹果酸或其衍生物。
• [EN] DERIVATIVES OF HYDROXAMIC ACID AS METALLOPROTEINASE INHIBITORS<br/>[FR] DERIVES D'ACIDE HYDROXAMIQUE UTILISES COMME INHIBITEURS DE METALLOPROTEINASES
  申请人：VERNALIS OXFORD LTD

  公开号：WO2005019194A1

  公开（公告）日：2005-03-03

  Compounds of formula (I) are inhibitors of matrix metalloproteinases, and are of use in the treatment of, for example fibrotic disease, multiple sclerosis, emphysemia, bronchitis and asthma: formula (I) wherein Ar represents an optionally substituted aryl, heteroaryl, C3-C8 cycloalkyl or heterocycloakyl group; R represents hydrogen or C1-C6 alkyl, or C3-C6 cycloalkyl; Alk represents a divalent C1-C5 alkylene or C2-C5 alkenylene radical; and R1 and R2 taken together with the nitrogen atom to which they are attached form a first heterocycloalkyl ring which is optionally fused to a second C3-C8 cycloalkyl or heterocycloalkyl ring, the said first and second rings being optionally substituted by at least one group of formula (II): formula (II) wherein m, p and n are independently 0 or 1; Z represents, hydrogen, or an optionally substituted carbocyclic or heterocyclic ring of from 5 to 7 ring atoms which is optionally fused to another optionally substituted carbocyclic or heterocyclic ring of from 5 to 7 ring atoms; Alk1 and Alk2 independently represent optionally substituted divalent C1-C3 alkylene radicals; X represents -0-, -S-, -S(O)-, -S(O2)-, -C(=O)-, -NH-, -NR3-, -S(O2)NH-, -S(O2)NR3-, -NHS(O2)-, or -NR3S(O2)-, where R3 is C1-C3 alkyl.

  式(I)的化合物是基质金属蛋白酶的抑制剂，并可用于治疗纤维化疾病、多发性硬化症、肺气肿、支气管炎和哮喘等疾病：式(I)中Ar代表可选择地取代的芳基、杂环芳基、C3-C8环烷基或杂环烷基基团；R代表氢或C1-C6烷基，或C3-C6环烷基；Alk代表二价的C1-C5烷基或C2-C5烯基基团；R1和R2与它们连接的氮原子一起形成第一杂环烷基环，该环可选择地与第二个C3-C8环烷基或杂环烷基环融合，所述的第一和第二环可选择地被至少一个式(II)的基团取代：式(II)中m、p和n独立地为0或1；Z代表氢，或由5至7个环原子组成的可选择地取代的碳环或杂环环，该环可选择地与另一个由5至7个环原子组成的可选择地取代的碳环或杂环环融合；Alk1和Alk2独立地代表可选择地取代的二价的C1-C3烷基基团；X代表-0-、-S-、-S(O)-、-S(O2)-、-C(=O)-、-NH-、-NR3-、-S(O2)NH-、-S(O2)NR3-、-NHS(O2)-或-NR3S(O2)-，其中R3为C1-C3烷基。
• [EN] N-HYDROXYAMIDE DERIVATIVES AND USE THEREOF<br/>[FR] DERIVES N-HYDROXYAMIDE ET LEUR APPLICATION
  申请人：APPLIED RESEARCH SYSTEMS

  公开号：WO2006010751A1

  公开（公告）日：2006-02-02

  The present invention is related to N-hydroxyamide derivatives of Formula (I) and use thereof, in particular for the treatment and/or prophylaxis of autoimmune disorders, inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, cancer, respiratory diseases and fibrosis, including multiple sclerosis, arthritis, emphysema, chronic obstructive pulmonary disease, liver and pulmonary fibrosis.

  本发明涉及式（I）的N-羟基酰胺衍生物及其用途，特别是用于治疗和/或预防自身免疫性疾病、炎症性疾病、心血管疾病、神经退行性疾病、癌症、呼吸道疾病和纤维化，包括多发性硬化症、关节炎、肺气肿、慢性阻塞性肺病、肝脏和肺部纤维化。
• Monocyclic beta-lactams and process for the preparation thereof
  申请人：University of Notre Dame du Lac

  公开号：US04992544A1

  公开（公告）日：1991-02-12

  Monocyclic .beta.-lactam compounds represented by the formula ##STR1## wherein R.sub.1 is H, NH.sub.2, acylamino, C.sub.1 -C.sub.4 alkyl, etc.; R.sub.2 is e.g. C.sub.1 -C.sub.4 alkyl, hydroxyalkyl, aminoalkyl, carboxy, esterified carboxy, esterified carboxyalkyl, or carboxyalkyl; and R.sub.3 is hydrogen, benzyl, substituted benzyl, pivaloyl, --SO.sub.3 M, or --P(C.dbd.O)(OM')2; are obtained by the cyclization of an O-substituted hydroxamate of a .beta.-substituted alkylcarboxylic acid. For example, .alpha.-ethylmalic acid monobenzyl ester is reacted with O-benzylhydroxylamine to form the O-benzylhydroxamate of the free carboxy group, and the hydroxamate is cyclized with diethyl diazodicarboxylate and triphenylphosphine to form the .beta.-lactam of the above formula wherein R.sub.1 is ethyl, R.sub.2 is benzyloxycarbonyl and R.sub.3 is benzyl. The .beta.-lactam compounds are useful intermediates for preparing .beta.-lactamase inhibitors and monocyclic .beta.-lactam antibiotics and, when R.sub.3 is --SO.sub.3 M or --P(C.dbd.O)(OM')2 the compounds and salts thereof are antibacterial agents.

  单环β-内酰胺化合物由以下公式表示：其中R.sub.1为H、NH.sub.2、酰胺基、C.sub.1 -C.sub.4烷基等；R.sub.2为例如C.sub.1 -C.sub.4烷基、羟基烷基、氨基烷基、羧基、酯化的羧基、酯化的羧基烷基或羧基烷基；R.sub.3为氢、苄基、取代苄基、对叔丁基、-SO.sub.3 M或-P(C.dbd.O)(OM')2；通过将β-取代烷基羧酸的O-取代羟酰胺环化而获得。例如，α-乙基苹果酸单苄酯与O-苄基羟胺反应形成自由羧基的O-苄基羟酰胺，然后将羟酰胺与双乙酰二氧化碳酸乙酯和三苯基膦环化，形成上述公式的β-内酰胺，其中R.sub.1为乙基，R.sub.2为苄氧羰基，R.sub.3为苄基。这些β-内酰胺化合物可用作制备β-内酰胺酶抑制剂和单环β-内酰胺抗生素的中间体，当R.sub.3为-SO.sub.3 M或-P(C.dbd.O)(OM')2时，化合物及其盐为抗菌剂。