ethyl 3-methyl-2-oxocyclopentaneacetate | 118326-03-7

• 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 3-methyl-2-oxocyclopentaneacetate
• 英文别名: <2-Oxo-3-methyl-cyclopentyl>-essigsaeure-ethylester；Ethyl (3-methyl-2-oxocyclopentyl)acetate；ethyl 2-(3-methyl-2-oxocyclopentyl)acetate
• CAS: 118326-03-7
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: ZSLFZZGDVRCOKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-methyl-2-oxocyclopentaneacetate 以60%的产率得到
  参考文献：
  名称：

  RAO, R. R.;SARKAR, RINA;BHATTACHARYA, SUKLA;MUKHERJEE, M. N., INDIAN J. CHEM., 26,(1987) N 10, 939-946

  摘要：

  DOI：
• 作为产物：
  描述：

  己二酸二乙酯 在 盐酸 、 sodium ethanolate 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 23.0h， 生成 ethyl 3-methyl-2-oxocyclopentaneacetate
  参考文献：
  名称：

  Cyclopentenyllithium additions to chiral aldehydes. Diastereofacial selectivity indicating the absence of a pronounced neighboring carboxylate anion effect

  摘要：

  The 1,2-addition of cyclopentenyllithium to a series of three five-membered aldehydo esters and their hemiacylals has been examined in order to assess the level and direction of facial selectivity surrounding nucleophilic attack at the aldehyde carbonyl and to clarify possible electronic and steric contributions stemming from neighboring functional groups. Neither methyl substitution of the acetic acid (ester) side chain nor the interchange of ester for carboxylate anion serve as important diastereocontrol elements. Instead, diastereofacial selectivity in these and related cyclic carboxaldehydes is governed by the inherent structural features of the ring system to which the functional group is attached. The convenient preparation of a complete subset of isomerically pure bicyclic lactones carrying five stereogenic centers is reported.

  DOI：

  10.1021/jo00012a013

文献信息

• Structure and stereochemistry of boschniakine, boschnialactone, and boschnialinic acid, an oxidation product of boschnialactone
  作者：T. Sakan、Y. Hayashi、Y. Honda、T. Shono、M. Nakajima、M. Kato

  DOI：10.1016/s0040-4020(01)92562-1

  日期：1967.1

  physiologically active principles of Boschniakia rossica Hunt, and their absolute structures have been determined. Four optically active stereoisomers of boschnialinic acid (2-carboxy-3-methylcyclopentylacetic acid), one of which is an oxidation product of boschnialactone, have been synthesized and their stereochemistries established.

  分离出Boschniakine C 10 H 11 NO和Boschnialactone C 9 H 14 O 2作为Boschniakia rossica Hunt的生理活性成分，并确定了它们的绝对结构。合成了四种波什尼亚林酸的光学活性立体异构体（2-羧基-3-甲基环戊基乙酸），其中之一是波什尼克内酯的氧化产物，并建立了它们的立体化学。
• Rao, R. R.; Sarkar, Rina; Bhattacharya, Sukla, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 939 - 946
  作者：Rao, R. R.、Sarkar, Rina、Bhattacharya, Sukla、Mukherjee, M. N.

  DOI：——

  日期：——
• FRIEDRICH, DIRK;PAQUETTE, LEO A., J. ORG. CHEM., 56,(1991) N2, C. 3831-3840
  作者：FRIEDRICH, DIRK、PAQUETTE, LEO A.

  DOI：——

  日期：——