methyl 5-(2-methyl-1,3-dioxolan-2-yl)pentanoate | 145068-76-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-(2-methyl-1,3-dioxolan-2-yl)pentanoate
• 英文别名: methyl 6,6-ethylenedioxyheptanoate；5-(2-methyl-[1,3]dioxolan-2-yl)-pentanoic acid methyl ester
• CAS: 145068-76-4
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: NSNPSDBQQPJHNC-UHFFFAOYSA-N

物化性质

• 沸点：
  247.4±15.0 °C(Predicted)
• 密度：
  1.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-(2-methyl-1,3-dioxolan-2-yl)pentanoate 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 5-(2-Methyl-1,3-dioxolan-2-yl)pentyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Potentiation of cADPR-Induced Ca²⁺-Release by Methylxanthine Analogues

  摘要：

  Caffeine and other methylxanthines are known to induce Ca2+-release from intracellular stores via the ryanodine receptor. In the present work, a range of caffeine analogues, in which methyl groups at the 1 and 7 positions were replaced with alkyl chains containing different functional groups (oxo, hydroxyl, propargyl, ester, and acids), were synthesized. These compounds were then screened for their ability to potentiate Ca2+-release induced by cADPR (an endogenous modulator of ryanodine receptors) in sea urchin egg homogenates. Two of the synthesized methylxanthines, 1,3-dimethyl-7-(7-hydroxyoctyl)xanthine (37) and 3-methyl-7-(7-oxooctyl)-1-propargylxanthine (66), were shown to be more potent than caffeine in potentiating cADPR-induced Ca2+-release, while 1,3-dimethyl-7-(5-ethylcarboxypentyl)xanthine (14) was shown to be more efficacious. The development of new methylxanthine analogues may lead to a better understanding of ryanodine receptor function and could possibly provide novel therapeutic agents.

  DOI：

  10.1021/jm980469t
• 作为产物：
  描述：

  5-乙酰基戊酸 在 硫酸 lithium tetrafluoroborate 作用下， 以 二氯甲烷 、 乙二醇 为溶剂， 反应 38.0h， 生成 methyl 5-(2-methyl-1,3-dioxolan-2-yl)pentanoate
  参考文献：
  名称：

  OXAZOLE AND THIAZOLE DERIVATIVES AS ALX RECEPTOR AGONISTS

  摘要：

  这项发明涉及式(I)的噁唑和噻唑衍生物，其中A、E、X、R1和R2如描述中所定义，它们的制备以及它们作为药用活性化合物的用途。

  公开号：

  US20120115916A1

文献信息

• Synthesis of (?)-Pinidinevia asymmetric, electrophilic enolate hydroxyamination/nitrone reduction
  作者：Wolfgang Oppolzer、Eric Merifield

  DOI：10.1002/hlca.19930760218

  日期：1993.3.24

  Enantiomerically pure(−)-pinidine (1) has been synthesized in 18.5% overall yield by a nine-step sequence starting from keto-ester 2. The key step 5 6 involves an asymmetric, electrophilic enolate hydroxyamination. Diastereoselective hydrogenation of nirtone 6 ensures the cis-relation between the substituents at C(2) and C(6) in piperidine 7.

  对映体纯的（-）-吡啶（1）已通过从酮酸酯2开始的九步法合成，以18.5％的总收率合成。关键步骤5 6涉及不对称的亲电烯醇式羟基胺化。内酯6的非对映选择性氢化可确保哌啶7中C（2）和C（6）处的取代基之间具有顺式关系。
• OXAZOLE AND THIAZOLE DERIVATIVES AS ALX RECEPTOR AGONISTS
  申请人：Bur Daniel

  公开号：US20120115916A1

  公开（公告）日：2012-05-10

  The invention relates to oxazole and thiazole derivatives of formula (I), wherein A, E, X, R 1 and R 2 are as defined in the description, their preparation and their use as pharmaceutically active compounds.

  这项发明涉及式(I)的噁唑和噻唑衍生物，其中A、E、X、R1和R2如描述中所定义，它们的制备以及它们作为药用活性化合物的用途。
• [EN] OXAZOLE AND THIAZOLE DERIVATIVES AS ALX RECEPTOR AGONISTS<br/>[FR] DÉRIVÉS DE L'OXAZOLE ET DU THIAZOLE EN TANT QU'AGONISTES DU RÉCEPTEUR ALX
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2010143158A1

  公开（公告）日：2010-12-16

  The invention relates to oxazole and thiazole derivatives of formula (I), wherein A, E, X, R1 and R2 are as defined in the description, their preparation and their use as pharmaceutically active compounds.

  这项发明涉及公式（I）中的噁唑和噻唑衍生物，其中A、E、X、R1和R2如描述中所定义，它们的制备以及它们作为药用活性化合物的用途。
• Asymmetric Synthesis of Cyclic α-Amino Phosphonates Using Masked Oxo Sulfinimines (<i>N</i>-Sulfinyl Imines)
  作者：Franklin A. Davis、Seung H. Lee、He Xu

  DOI：10.1021/jo040127x

  日期：2004.5.1

  Five-, six-, and seven-membered cyclic α-amino phosphonates, amino acid surrogates, are prepared in enantiomerically pure form via the highly diastereomeric addition of metal phosphonates to masked oxo sulfinimines. Hydrolysis of the resulting masked oxo α-amino phosphonates followed by reduction of the intermediate cyclic imino phosphonates affords the title compounds in good yield.

  五，六和七元环状α-氨基膦酸酯（氨基酸替代物）是通过将金属膦酸酯高度非对映异构体加到被掩盖的氧亚磺胺上而制成对映体纯形式的。水解所得的掩蔽的羰基α-氨基膦酸酯，然后还原中间体环状亚氨基膦酸酯，以良好的收率得到标题化合物。
• Oxazole and thiazole derivatives as ALX receptor agonists
  申请人：Bur Daniel

  公开号：US08674111B2

  公开（公告）日：2014-03-18

  The invention relates to oxazole and thiazole derivatives of formula (I), wherein A, E, X, R1 and R2 are as defined in the description, their preparation and their use as pharmaceutically active compounds.

  本发明涉及公式(I)的噁唑和噻唑衍生物，其中A、E、X、R1和R2的定义如描述中所述，它们的制备以及它们作为药物活性化合物的用途。