(1R,3R)-1-hydroxy-3-(methyl-carboxymethyl)-4-cyclopentene | 426225-93-6

• 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: (1R,3R)-1-hydroxy-3-(methyl-carboxymethyl)-4-cyclopentene
• 英文别名: (1R,4S)-4-hydroxycyclopent-2-en-1-essigsaeure-methylester；Methyl 2-[(1R,4R)-4-hydroxycyclopent-2-en-1-yl]acetate
• CAS: 426225-93-6
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: SOVNDLFKPGLMEE-RQJHMYQMSA-N

物化性质

• 沸点：
  234.2±23.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,3R)-1-hydroxy-3-(methyl-carboxymethyl)-4-cyclopentene 在 偶氮二异丁腈 、 3 A molecular sieve 、 碘 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 水 、 xylene 、 苯 为溶剂， 反应 4.0h， 生成 (1S,5R)-6-carbomethoxymethyl-2-oxabicyclo[3.3.0]-oct-3-one
  参考文献：
  名称：

  甲基茉莉酮：通过钯（0）-induzierte，对映异构体Alkylierung von Cyclopent-2-en-1,3-diol- Derivaten的Ein kurzer Weg zum Naturstoff和SeinemUnnatürlichen对映异构体

  摘要：

  茉莉酸甲酯：天然存在的茉莉酸甲酯和其非天然映异构体A短合成通过由钯环戊-2-烯-1,3-二醇衍生物的烷基化Enantiodivergent（0）诱导的反应

  DOI：

  10.1002/hlca.19890720822
• 作为产物：
  描述：

  methyl 2-((1R,4R)-4-(trityloxy)cyclopent-2-en-1-yl)acetate 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 1.25h， 以39%的产率得到(1R,3R)-1-hydroxy-3-(methyl-carboxymethyl)-4-cyclopentene
  参考文献：
  名称：

  Regulation of type 5 adenylyl cyclase for treatment of neurodegenerative and cardiac diseases

  摘要：

  这项发明涉及含有一种或多种能够有效调节第5型腺苷酸环化酶活性的化合物的药物组合物，以及治疗神经系统疾病和障碍、以及由此引起的运动功能丧失的方法，以及用于治疗心脏疾病和疾病的方法，包括以异常心率为特征的情况。

  公开号：

  US20060252774A1

文献信息

• Synthesis of All Stereoisomeric Carbapentofuranoses
  作者：Christoph Marschner、Judith Baumgartner、Herfried Griengl

  DOI：10.1021/jo00121a046

  日期：1995.8

  All carbocyclic analogs of the pentofuranoses were synthesized starting from norborn-5-en-2-one (1). By using either base- or acid-catalyzed Baeyer-Villiger reaction of 1, the central intermediates 2 and 3 were obtained. The required functionalization of the olefinic double bond was achieved either by cis-hydroxylation in the case of the ribo, lyre, and alpha-xylo derivatives or by epoxidation and subsequent opening with aqueous perchloric acid. In the latter case, a pronounced selectivity for opening the epoxy alcohol in the 3-position was found. If an epoxy acetate with both functions on the same side of the ring was used, the epoxide was opened in the 2-position by neighboring group participation of the acetate. The requisite side chain degradation was accomplished either by conversion of the ester into an olefin and subsequent dihydroxylation/cleavage reaction or by Curtius rearrangement to the amine and its conversion into an acetate.
• Metal Coordination-Based Inhibitors of Adenylyl Cyclase:  Novel Potent P-Site Antagonists
  作者：Daniel E. Levy、Ming Bao、Diana B. Cherbavaz、James E. Tomlinson、David M. Sedlock、Charles J. Homcy、Robert M. Scarborough

  DOI：10.1021/jm0205604

  日期：2003.5.1

  The adenylyl cyclases (ACS) are a family of intracellular enzymes associated with signal transduction by virtue of their ability to convert ATP to cAMP. The catalytic mechanism of this transformation proceeds through initial binding of ATP to the so-called purine binding site (P-site) of the enzyme followed by metal-mediated cyclization with loss of pyrophosphate. Crystallographic analysis of ACs with known inhibitors reveals the presence of two metals in the active site. Presently, nine isoforms of adenylyl cyclase are known, and unique isoform combinations are expressed in a tissue-specific manner. The development of isoform-specific inhibitors of adenylyl cyclase may prove to be a useful strategy toward the design of unique signal transduction inhibitors. To develop novel AC inhibitors, we have chosen an approach to inhibitor design utilizing an adenine ring system joined to a metal-coordinating hydroxamic acid via various linkers. Previous work in our group has validated this approach and identified novel inhibitors that possess an adenine ring joined to a metal-coordinating hydroxamic acid through flexible acyclic linkers (Levy, D. E., et al. Bioorg. Med. Chem. Lett. 2002, 12, 30853088). Subsequent studies have focused on the introduction of conformational restrictions into the tether of the inhibitors with the goal of increasing potency (Levy, D. E., et al. Bioorg. Med. Chem. Lett. 2002, 12, 3089-3092). Building upon the favorable spatial positioning of the adenine and hydroxamate groups coupled with potentially favorable entropic factors, the unit joining the carbocycle to the hydroxamate was explored further and a stereochemical-based SAR was elucidated, leading to a new series of highly potent AC inhibitors.
• CHENG, PETER T. W.;MCLEAN, STEWART, CAN. J. CHEM., 67,(1989) N, C. 261-267
  作者：CHENG, PETER T. W.、MCLEAN, STEWART

  DOI：——

  日期：——
• Regulation of type 5 adenylyl cyclase for treatment of neurodegenerative and cardiac diseases
  申请人：Vatner F. Stephen

  公开号：US20060252774A1

  公开（公告）日：2006-11-09

  The invention concerns pharmaceutical compositions that contain a compound or compounds that can effectively regulate the activity of Type 5 Adenylyl Cyclase and methods for treatment of neurological diseases and disorders, as well as motor function loss therefrom, as well as treatment for cardiac conditions and diseases including conditions characterized by abnormal heart rate.

  这项发明涉及含有一种或多种能够有效调节第5型腺苷酸环化酶活性的化合物的药物组合物，以及治疗神经系统疾病和障碍、以及由此引起的运动功能丧失的方法，以及用于治疗心脏疾病和疾病的方法，包括以异常心率为特征的情况。
• Methyl-jasmonat: Ein kurzer Weg zum Naturstoff und seinem unnatürlichen Enantiomer<i>via</i>Palladium(0)-induzierte, enantiodivergente Alkylierung von Cyclopent-2-en-1,3-diol-Derivaten
  作者：Franz-Peter Montforts、Ingrid Gesing-Zibulak、Wassilios Grammenos、Manfred Schneider、Kurt Laumen

  DOI：10.1002/hlca.19890720822

  日期：1989.12.13

  Methyl Jasmonate: A Short Synthesis of Naturally Occurring Methyl Jasmonate and its Unnatural Enantiomer via Enantiodivergent Alkylation of Cyclopent-2-ene-1,3-diol Derivatives by Palladium(0)-Induced Reactions

  茉莉酸甲酯：天然存在的茉莉酸甲酯和其非天然映异构体A短合成通过由钯环戊-2-烯-1,3-二醇衍生物的烷基化Enantiodivergent（0）诱导的反应