Ethyl hydrogen 2-cyclopentylpropanedioate | 94488-95-6

• 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: Ethyl hydrogen 2-cyclopentylpropanedioate
• 英文别名: monoethyl (+/-)-cyclopentylmalonate；Cyclopentylmalonsaeure-monoethylester；2-Cyclopentyl-3-ethoxy-3-oxopropanoic acid
• CAS: 94488-95-6
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: DEILPHAKPLECAF-UHFFFAOYSA-N

物化性质

• 沸点：
  325.5±25.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  Ethyl hydrogen 2-cyclopentylpropanedioate 在 manganese(IV) oxide 、 聚合甲醛 、 sodium acetate 、 二异丁基氢化铝 、 溶剂黄146 、 二乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 101.0h， 生成 2-cyclopentylacrylaldehyde
  参考文献：
  名称：

  Total synthesis of spatol and other spatane diterpenes

  摘要：

  Total syntheses of three spatane diterpenes stoechospermol (1), 5(R),15(R),18-trihydroxyspata-13,16(E)-diene (2), and (+)-spatol (3) were accomplished from a common intermediate, diol 7. The total synthesis established as R the absolute configuration at the 15-position in 2. Novel stereospecific transformations of 2,3-epoxy-1,4-diols into vicinal diepoxides were demonstrated and exploited for assembling the sensitive allylic diepoxide in the side chain of spatol. This new synthetic method allows the conversion of both 1,2-threo-2,3-trans- and 1,2-erythro-2,3-trans-2,3-epoxy-1,4-diols into vicinal 1,2-cis-2,3-erythro-1,3-diepoxides. Unexpected stability toward hydroxide anion was found for the allylic diepoxide functional array. This observation provides presumptive evidence that acid catalysis is operative in the epoxide cleaving substitution reaction of spatol by the weakly nucleophilic chloride anion that gives chlorohydrin 4. A proclivity for erythro-selective epoxidation of allylic silyl ethers was found. The utility of C-silyl substituents for reversing this stereoselectivity, i.e., favoring threo-selective epoxidation of allylic silyl ethers, was established.

  DOI：

  10.1021/ja00008a044
• 作为产物：
  描述：

  环戊基丙二酸二乙酯 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以86%的产率得到Ethyl hydrogen 2-cyclopentylpropanedioate
  参考文献：
  名称：

  Nitration of α,β-unsaturated esters. Evidence for positive charge build-up adjacent to carbonyl carbon

  摘要：

  在用四氟硼酸亚硝酰进行某些α,β-不饱和酯的硝化反应中形成的活性中间体表现出高度活性α-羰基阳离子的预期行为。已观察到三种诊断性的反应类型，表明这些不稳定的阳离子的存在：（i）在Ritter反应中捕获，（ii）从丙基阳离子形成环丙烷，（iii）烷基的Wagner-Meerwein迁移。对所提出的中间阳离子的相对气相稳定性的半经验计算有助于合理化观察到的化学现象。

  DOI：

  10.1039/a607170h

文献信息

• [EN] NEW IKACH BLOCKERS<br/>[FR] NOUVEAUX BLOQUANTS DE L'IKACH
  申请人：ASTRAZENECA AB

  公开号：WO2012074469A1

  公开（公告）日：2012-06-07

  The invention relates to compounds according to Formula (I): or a pharmaceutically acceptable salt thereof, wherein m, n, R1, R2, R3, R4, R5, x and y are as defined herein. Compounds according to Formula (I) are pharmacologically effective as potassium channel inhibitors, in particular inhibitors of the acetylcholine operated inward rectifying potassium channel current (i.e. IKACh blockers), and are believed to be useful in the treatment of cardiac arrhythmias, in particular supraventricular tacharrhythmias, such as atrial fibrillation and atrial flutter.

  该发明涉及按照公式(I)的化合物或其药用可接受的盐，其中m、n、R1、R2、R3、R4、R5、x和y如本文所定义。公式(I)的化合物在药理学上作为钾通道抑制剂具有药效，特别是乙酰胆碱激活的向内整流钾通道电流的抑制剂（即IKACh阻滞剂），并被认为在治疗心律失常方面有用，特别是在尤为心室上速心律失常，如心房颤动和心房扑动的治疗中。
• Compounds and their use as IKACh blockers
  申请人：Bostrõm Jonas

  公开号：US08361998B2

  公开（公告）日：2013-01-29

  The invention relates to compounds according to Formula I: or a pharmaceutically acceptable salt thereof, wherein m, n, R1, R2, R3, R4, R5, x and y are as defined herein. Compounds according to Formula I are pharmacologically effective as potassium channel inhibitors, in particular inhibitors of the acetylcholine operated inward rectifying potassium channel current (i.e. IKACh blockers), and are believed to be useful in the treatment of cardiac arrhythmias, in particular supraventricular tacharrhythmias, such as atrial fibrillation and atrial flutter.

  本发明涉及公式I所示的化合物或其药学上可接受的盐，其中m、n、R1、R2、R3、R4、R5、x和y的定义如本文所述。公式I所示的化合物在药理学上具有钾通道抑制剂的作用，特别是乙酰胆碱操作的内向整流钾通道电流（即IKACh阻滞剂），并且被认为在治疗心律失常方面有用，特别是上室性心动过速，如心房颤动和心房扑动。
• COMPOUNDS AND THEIR USE AS IKACH BLOCKERS
  申请人：AstraZeneca AB

  公开号：US20130143858A1

  公开（公告）日：2013-06-06

  The invention relates to compounds according to Formula I: or a pharmaceutically acceptable salt thereof, wherein m, n, R 1 , R 2 , R 3 , R 4 , R 5 , x and y are as defined herein. Compounds according to Formula I are pharmacologically effective as potassium channel inhibitors, in particular inhibitors of the acetylcholine operated inward rectifying potassium channel current (i.e. IKACh blockers), and are believed to be useful in the treatment of cardiac arrhythmias, in particular supraventricular tacharrhythmias, such as atrial fibrillation and atrial flutter.

  本发明涉及以下式I的化合物或其药学上可接受的盐，其中m、n、R1、R2、R3、R4、R5、x和y的定义如本文所述。式I的化合物作为钾通道抑制剂具有药理学作用，特别是乙酰胆碱操作的内向整流钾通道电流（即IKACh阻滞剂），并被认为在治疗心律失常方面有用，特别是上室性心动过速，如心房颤动和心房扑动。
• NOVEL MALONIC ACID SULFONAMIDE DERIVATIVE AND PHARMACEUTICAL USE THEREOF
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：EP2172450B9

  公开（公告）日：2014-10-08
• US8361998B2
  申请人：——

  公开号：US8361998B2

  公开（公告）日：2013-01-29