ethyl 3-cyclopentylpropiolate | 17931-62-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-cyclopentylpropiolate
• 英文别名: cyclopentyl-propynoic acid ethyl ester；Cyclopentyl-propiolsaeureethylester；2-Propynoic acid, 3-cyclopentyl-, ethyl ester；ethyl 3-cyclopentylprop-2-ynoate
• CAS: 17931-62-3
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: FCLITGRQJGLLII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 3-cyclopentylpropiolate 在 三环己基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 25.0h， 生成 Ethyl 2-(2,2-dicyano-1-cyclopentylethenyl)pent-4-enoate
  参考文献：
  名称：

  通过烯丙基丙二腈的1,4-连续加成和烷基酯平台上的Cope重排进行双向碳链延伸

  摘要：

  建立了一个一锅法，将两个不同的三个碳原子单元（烯丙基和丙二腈官能团）区域选择性引入CC三键。转化过程是通过膦催化的烯丙基丙二腈向膦酸酯的1,4-加成反应以及微波加热的Cope重排而实现的，从而在炔酸酯平台上实现了双向碳链延伸。操作简单，简洁的碳骨架结构和高原子经济性应使本方法对结构复杂的有机分子的合成具有吸引力。

  DOI：

  10.1016/j.tetlet.2015.11.081
• 作为产物：
  描述：

  环戊基甲醛 、 氯甲酸乙酯 在 四溴化碳 、 三苯基膦 、 正丁基锂 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 2.5h， 生成 ethyl 3-cyclopentylpropiolate
  参考文献：
  名称：

  Structural design and synthesis of arylalkynyl amide-type peroxisome proliferator-activated receptor γ (PPARγ)-selective antagonists based on the helix12-folding inhibition hypothesis

  摘要：

  Peroxisome proliferator-activated receptor gamma (PPAR gamma) antagonists are candidates for treatment of type 2 diabetes, obesity and osteoporosis. However, few rational design strategies are currently available. Here, we utilized the helix12 (H12)-folding inhibition hypothesis, in combination with our previously determined X-ray crystal structure of PPAR gamma agonist MEKT-21 (6) complexed with the PPAR gamma ligand-binding domain, to design and develop a potent phenylalkynyl amide-type PPAR gamma antagonist 9i, focusing initially on pinpoint structural modification of the propanoic acid moiety of 6. Since 9i retained very weak, but distinct, PPAR gamma agonist activity, we next modified the distal benzene ring of 9i, aiming to delete the residual PPAR gamma agonist activity while retaining the antagonist activity. Introduction of a chlorine atom at the 2-position of the distal benzene ring afforded 9p, which exhibited potent, PPAR gamma-selective full antagonist activity without detectable agonist activity. We found that 9p stabilized the corepressor PPAR gamma complex and suppressed basal PPAR gamma activity. This compound showed anti-adipogenesis activity at the cellular level. This agonist antagonist switching concept based on the H12-folding inhibition hypothesis should also be applicable for designing other classes of PPAR gamma full antagonists. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.017

文献信息

• Reverse Regioselectivity in the Palladium(II) Thiourea Catalyzed Intermolecular Pauson-Khand Reaction
  作者：Na Wu、Lujiang Deng、Lianzhu Liu、Qi Liu、Chuangchuang Li、Zhen Yang

  DOI：10.1002/asia.201200783

  日期：2013.1

  Which way? Palladium thiourea catalyzed Pauson–Khand reaction of norbornene with substituted alkynoates to afford selectively either α‐carboxylated adducts or β‐carboxylated adducts with the reverse regioselectivity has been demonstrated for the first time. Control of the regioselectivity in this transformation is governed by the addition of LiCl. A mechanistic interpretation to account for this observed

  哪一条路？首次证明了钯硫脲催化降冰片烯与取代的炔酸酯的Pauson-Khand反应，可选择性地提供具有反向区域选择性的α-羧化加合物或β-羧化加合物。通过添加LiCl来控制该转化中的区域选择性。提出了一种机械解释来解释这种观察到的区域选择性。
• Chemo-, Regio-, and Stereoselective Copper(II)-Catalyzed Boron Addition to Acetylenic Esters and Amides in Aqueous Media
  作者：Amanda K. Nelson、Cheryl L. Peck、Sean M. Rafferty、Webster L. Santos

  DOI：10.1021/acs.joc.6b00648

  日期：2016.5.20

  Aqueous conditions were developed for conducting an open-to-air, copper(II)-catalyzed addition of pinBBdan to alkynoates and alkynamides. The simple and mild β-borylation protocol proceeds in a remarkably chemo-, regio-, and stereoselective fashion to afford 1,8-diaminonaphthalene protected (Z)-β-boryl enoates and primary, secondary, and tertiary enamides in good to excellent yields. These reactions

  开发了在露天条件下进行铜（II）催化的pinBBdan加至炔酸和炔酰胺中的露天条件。简单而温和的β-硼化协议以显着的化学，区域和立体选择性方式进行，从而以良好的产率提供了1,8-二氨基萘保护的（Z）-β-硼烯酸酯和伯，仲和叔酰胺。 。这些反应显示出对各种烷基，芳基和杂原子官能团的高耐受性，并提供了对各种乙烯基硼酸衍生物的方便获得。
• SUBSTITUTED DIHYDRO AND TETRAHYDRO OXAZOLOPYRIMIDINONES, PREPARATION AND USE THEREOF
  申请人：CAO Bin

  公开号：US20100075994A1

  公开（公告）日：2010-03-25

  The present invention relates to a series of substituted dihydro and tetrahydro oxazolopyrimidinones, specifically, to a series of 2-substituted-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-ones and 2-substituted-2,3,5,6-tetra-hydro-oxazolo[3,2-a]pyrimidin-7-ones of formula (I): Wherein p, n, X, Y, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are as defined herein. This invention also relates to methods of making these compounds including novel intermediates. The compounds of this invention are modulators of metabotropic glutamate receptors (mGluR), particularly, mGluR2 receptor. Therefore, the compounds of this invention are useful as pharmaceutical agents, especially in the treatment and/or prevention of a variety of central nervous system disorders (CNS), including but not limited to acute and chronic neurodegenerative conditions, psychoses, convulsions, anxiety, depression, migraine, pain, sleep disorders and emesis.

  本发明涉及一系列取代二氢和四氢噁唑嘧啶酮，具体地说，涉及一系列式(I)的2-取代-2,3-二氢-噁唑并[3,2-a]嘧啶-7-酮和2-取代-2,3,5,6-四氢-噁唑并[3,2-a]嘧啶-7-酮： 其中p、n、X、Y、R1、R2、R3、R4、R5、R6、R7和R8如本文所定义。本发明还涉及制备这些化合物的方法，包括新颖的中间体。本发明的化合物是代谢型谷氨酸受体（mGluR）的调节剂，特别是mGluR2受体。因此，本发明的化合物在药物制剂中具有用途，特别是在治疗和/或预防各种中枢神经系统疾病（CNS）方面，包括但不限于急性和慢性神经退行性疾病、精神病、癫痫、焦虑、抑郁、偏头痛、疼痛、睡眠障碍和呕吐。
• SELECTIVE ESTROGEN RECEPTOR MODULATOR COMPOSITIONS AND METHODS FOR TREATMENT OF DISEASE
  申请人：Scanlan Thomas S.

  公开号：US20090124698A1

  公开（公告）日：2009-05-14

  The present disclosure concerns a new class of selective estrogen receptor modulators (SERMs). The disclosure also includes the identification of a previously unknown membrane associated estrogen receptor. Methods for making and using the disclosed SERMs are disclosed, including pharmaceutical formulations of the disclosed novel compounds in useful compositions.

  本公开涉及一类新型选择性雌激素受体调节剂（SERMs）。该公开还包括先前未知的膜相关雌激素受体的鉴定。公开了制备和使用所述SERMs的方法，包括所述新型化合物的药物配方在有用组合物中的使用。
• Ru-Catalyzed Regioselective Cascade Annulation of Acrylamides with 2-Alkynoates for the Synthesis of Various 6-Oxo Nicotinic Acid Esters
  作者：Dnyaneshwar N. Garad、Santosh B. Mhaske

  DOI：10.1021/acs.joc.8b02783

  日期：2019.2.15

  of acrylamides with 2-alkynoates via aza-Michael/C–H activation sequence for the synthesis of various 6-oxo nicotinic acid esters is described. The regioselectivity of the protocol has been confirmed by performing silver mediated protodecarboxylation of the corresponding 6-oxo nicotinic acid to furnish 2-pyridone. The developed protocol is copper or silver salt-free and uses inexpensive, safe, and

  描述了Ru催化的丙烯酰胺与2-炔酸酯通过氮杂-Michael / CH活化序列合成的6-氧代烟酸酯的区域选择性级联环化反应。通过进行相应的6-氧代烟酸的银介导的原脱羧以提供2-吡啶酮，已经证实了该方案的区域选择性。所开发的方案不含铜或银盐，并使用廉价，安全且对环境无害的基于过氧化物的“氧酮”作为唯一氧化剂。还演示了该协议的氧化还原中性版本。