malonsaeure-monocyclohexylester | 91851-80-8

• 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: malonsaeure-monocyclohexylester
• 英文别名: 3-(Cyclohexyloxy)-3-oxopropanoic acid；3-cyclohexyloxy-3-oxopropanoic acid
• CAS: 91851-80-8
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: OMHQOKGHQPULBU-UHFFFAOYSA-N

物化性质

• 熔点：
  172-173 °C (decomp)
• 沸点：
  140-170 °C(Press: 14 Torr)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  malonsaeure-monocyclohexylester 在 O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以90%的产率得到1,3-acetonedicarboxylic acid dicyclohexyl ester
  参考文献：
  名称：

  活化丙二酸半酯的自缩合：聚酮化合物生物合成中脱羧性克莱森缩合的模型

  摘要：

  丙二酸半含氧酸酯与N-羟基琥珀酰亚胺基酯形成试剂的反应导致自缩合，从而提供相应的1，3-丙酮二羧酸二酯。此新方法不需要二价金属螯合剂或配位溶剂即可成功缩合。

  DOI：

  10.1016/j.tetlet.2003.08.014
• 作为产物：
  描述：

  Malonsaeure-dicyclohexylester 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以80.8%的产率得到malonsaeure-monocyclohexylester
  参考文献：
  名称：

  Xia, Chun-Nian; Hu, Wei-Xiao, Journal of Chemical Research, 2005, # 5, p. 332 - 334

  摘要：

  DOI：

文献信息

• OXIDATIVE COUPLING OF ARYL BORON REAGENTS WITH SP3-CARBON NUCLEOPHILES, AND AMBIENT DECARBOXYLATIVE ARYLATION OF MALONATE HALF-ESTERS VIA OXIDATIVE CATALYSIS
  申请人：The Governors of the University of Alberta

  公开号：US20180186721A1

  公开（公告）日：2018-07-05

  Described herein are methods of oxidative coupling of aryl boron reagents with sp 3 -carbon nucleophiles, and ambient decarboxylative arylation of malonate half-esters via oxidative catalysis.

  本文描述了一种利用氧化偶联芳基硼试剂与sp3-碳亲核试剂进行反应的方法，以及通过氧化催化实现马隆酸半酯的环境脱羧芳基化。
• Ni(II)-Catalyzed Enantioselective Synthesis of β-Hydroxy Esters with Carboxylate Assistance
  作者：Na Wang、Hongxin Liu、Hang Gao、Jiafeng Zhou、Longzhangdi Zheng、Juan Li、Hong-Ping Xiao、Xinhua Li、Jun Jiang

  DOI：10.1021/acs.orglett.9b02297

  日期：2019.9.6

  decarboxylative aldol reaction between malonic acid half-oxyesters and various carbonyls with carboxylate assistance was developed, affording structurally diverse β-hydroxy esters with good yields and enantioselectivities under mild conditions. Importantly, the broad substrate scope of this methodology enabled rapid accesses to several natural products and their analogues as exemplified by phenylpropanoid, phaitanthrin

  建立了Ni-恶唑啉配合物催化丙二酸半含氧酸酯和各种羰基在羧酸酯辅助下的不对称脱羧醛醇缩合反应，在温和条件下以良好的收率和对映选择性提供了结构多样的β-羟基酯。重要的是，这种方法的广泛的底物范围使人们能够快速获得几种天然产物及其类似物，例如苯丙烷，类赤霉素B和邻苯二甲酸酯。
• Stoffwechselprodukte von Mikroorganismen 226. Mitteilung Versuche zur Strukturaufklärung von Niphimycin, 3. Teil. Identität von Scopafungin mit Niphimycin I und Lage des Malonylrestes in Niphimycin und Copiamycin
  作者：Peter Gassmann、Leonhard Hagmann、Walter Keller-Schierlein、Daniel Samain

  DOI：10.1002/hlca.19840670309

  日期：1984.5.2

  Structural Elucidation of Niphimycin, Part 3. Identity of Scopafungin and Niphimycin I. Position of the Malonyl Residue of Niphimycin and Copiamycin

  尼古丁的结构解析，第3部分。司可芬净和尼古丁的鉴定I.尼古丁和卡波霉素丙二酸残基的位置
• A New Strategy for the Construction of α-Amino Acid Esters via Decarboxylation
  作者：Jie Zhang、Jiewen Jiang、Yuling Li、Yun Zhao、Xiaobing Wan

  DOI：10.1021/ol401139m

  日期：2013.7.5

  A new alpha-amino acid esters formation reaction has been developed via decarboxylation. The methodology is distinguished by its practical novelty in terms of the readily accessible starting materials, environmentally benign reaction conditions and waste streams, and wide substrate scope.
• Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines
  作者：Chun-nian Xia、Hai-bo Li、Feng liu、Wei-xiao Hu

  DOI：10.1016/j.bmcl.2008.10.046

  日期：2008.12

  Forty caffeate analogues were synthesized via a convenient method starting from vanillin with moderate to good yields. The testing of biological activity of these compounds against HIV-1 integrase indicates that four compounds: bornyl caffeate, bornyl 2-nitrocaffeate, 5-nitrocaffeic acid and 5-nitrocaffeic acid phenethyl ester (5-nitroCAPE) possess a good HIV integrase inhibitory activity, IC50 19.9, 26.8, 25.0 and 13.5 mu M, respectively. Twelve caffeate analogues were tested by MTT assay on growth of human hepatocellular carcinoma BEL-7404, human breast MCF-7 adenocarcinoma, human lung A549 adenocarcinoma and human gastric cancer BCG823 cell lines, respectively. And the best result is IC50 5.5 mu M for CAPE against BEL-7404. (C) 2008 Elsevier Ltd. All rights reserved.