ethyl 3-cyclopentylidenepropanoate | 17343-84-9

• 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-cyclopentylidenepropanoate
• 英文别名: Ethyl 3-cyclopentylidenepropanoate
• CAS: 17343-84-9
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: OKMHTAOQPMOHJA-UHFFFAOYSA-N

物化性质

• 沸点：
  230.4±9.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  4
• 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-cyclopentylidenepropanoate 在 吡啶 、 lithium aluminium deuteride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 3-cyclopentylidene<1,1-2H>-1-propanol tosyl ester
  参考文献：
  名称：

  Engel, Paul S.; Culotta, Anne Marie, Journal of the American Chemical Society, 1991, vol. 113, # 7, p. 2686 - 2696

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-ethyl 3-cyclopentylprop-2-enoate 在 (isomerization) 作用下， 生成 ethyl 3-cyclopentylidenepropanoate
  参考文献：
  名称：

  Reaction of epoxides with tri-n-butylcarbethoxymethylidenephosphorane. Formation of unsaturated esters

  摘要：

  DOI：

  10.1021/ja00999a020

文献信息

• Cobalt(<scp>i</scp>)-catalysed CH-alkylation of terminal olefins, and beyond
  作者：Maciej Giedyk、Katarzyna Goliszewska、Keith ó Proinsias、Dorota Gryko

  DOI：10.1039/c5cc07363d

  日期：——

  Cobalester, a natural nontoxic vitamin B12 derivative was found to catalyse unusual olefinic sp2 C-H alkylation with diazo reagents as a carbene source instead of the expected cyclopropanation.

  发现钴胺酸酯是一种天然的无毒维生素B12衍生物，使用重氮试剂作为卡宾源而不是预期的环丙烷化，可催化异常的烯烃sp2 CH烷基化。
• Facile Preparation of Functionalized 1-Substituted Cycloalkenes via an Iodine Atom Transfer Radical Addition–Elimination Process
  作者：Philippe Renaud、Daniel Meyer、Estelle Vin、Benjamin Wyler、Guillaume Lapointe

  DOI：10.1055/s-0035-1560555

  日期：——

  scalable two-step one-pot procedure for the preparation of cycloalkenes substituted with a functionalized alkyl side chain is reported. This method is based on a triethylborane-mediated iodine atom transfer radical addition (ATRA) of 1-iodoesters and related compounds to methylenecycloalkanes followed by treatment of the intermediate tertiary iodide with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to

  报道了一种有效且可扩展的两步一锅法，用于制备被官能化烷基侧链取代的环烯烃。该方法基于 1-碘酯和相关化合物与亚甲基环烷烃的三乙基硼烷介导的碘原子转移自由基加成 (ATRA)，然后用 1,8-二氮杂双环 [5.4.0] 十一碳烯处理中间体叔碘化物(DBU) 以促进选择性内源消除。
• Degenerative xanthate transfer to olefins under visible-light photocatalysis
  作者：Atsushi Kaga、Xiangyang Wu、Joel Yi Jie Lim、Hirohito Hayashi、Yunpeng Lu、Edwin K L Yeow、Shunsuke Chiba

  DOI：10.3762/bjoc.14.283

  日期：——

  The degenerative transfer of xanthates to olefins is enabled by the iridium-based photocatalyst [IrdF(CF3)ppy}2(dtbbpy)](PF6) under blue LED light irradiation. Detailed mechanistic investigations through kinetics and photophysical studies revealed that the process operates under a radical chain mechanism, which is initiated through triplet-sensitization of xanthates by the long-lived triplet state

  在蓝色LED光照射下，铱基光催化剂[Ir dF（CF3）ppy} 2（dtbbpy）]（PF6）能够使黄原酸酯退化转化为烯烃。通过动力学和光物理研究进行的详细机械研究表明，该过程在自由基链机制下运行，该机制是通过铱基光催化剂的长寿命三重态通过对黄药的三重敏化而引发的。
• Coupling Reaction of Alkenes with α-Bromo Carboxylic Acid Derivatives Using Nickel Boride and Borohydride Exchange Resin in Methanol
  作者：Meyoung Ju Joung、Jin Hee Ahn、Dong Won Lee、Nung Min Yoon

  DOI：10.1021/jo972019z

  日期：1998.4.1
• Discovery of (3<i>S</i>,3a<i>R</i>)-2-(3-Chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2<i>H</i>-benzo[<i>g</i>]indazole-7-carboxylic Acid (PF-3882845), an Orally Efficacious Mineralocorticoid Receptor (MR) Antagonist for Hypertension and Nephropathy
  作者：Marvin J. Meyers、Graciela B. Arhancet、Susan L. Hockerman、Xiangyang Chen、Scott A. Long、Matthew W. Mahoney、Joseph R. Rico、Danny J. Garland、James. R. Blinn、Joe T. Collins、Shengtian Yang、Horng-Chih Huang、Kevin F. McGee、Jay M. Wendling、Jessica D. Dietz、Maria A. Payne、Bruce L. Homer、Marcia I. Heron、David B. Reitz、Xiao Hu

  DOI：10.1021/jm100505n

  日期：2010.8.26

  We have discovered a novel class of nonsteroidal pyrazoline antagonists of the mineralocorticoid receptor (M R) that show excellent potency and selectivity against other nuclear receptors. Early analogues were poorly soluble and had a propensity to inhibit the hERG channel. Remarkably, both of these challenges were overcome by incorporation of a single carboxylate moiety. Structural modification of carboxylate-containing lead R-4g with a wide range of substituents at each position of the pyrazoline ring resulted in R-12o, which shows excellent activity against MR and reasonable pharmacokinetic profile. Introduction of conformational restriction led to a novel series characterized by exquisite potency and favorable steroid receptor selectivity and pharmacokinetic profile. Oral dosing of 3S,3aR-27d (PF-3882845) in the Dahl salt sensitive preclinical model of salt-induced hypertension and nephropathy showed blood pressure attenuation significantly greater than that with eplerenone, reduction in urinary albumin, and renal protection. As a result of these findings, 3S,3aR-27d was advanced to clinical studies.