3-Methyl-cyclopentan-2-one-1-acetic acid | 90199-49-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Methyl-cyclopentan-2-one-1-acetic acid
• 英文别名: (3-methyl-2-oxo-cyclopentyl)-acetic acid；(3-Methyl-2-oxo-cyclopentyl)-essigsaeure；1-Methyl-3-carboxymethyl-cyclopentanon-(2)；2-(3-Methyl-2-oxocyclopentyl)acetic acid
• CAS: 90199-49-8
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: UTMPTYYKUNIMPD-UHFFFAOYSA-N

物化性质

• 沸点：
  112 °C(Press: 10 Torr)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Methyl-cyclopentan-2-one-1-acetic acid 以62%的产率得到(3aR,6aR)-6-methyl-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
  参考文献：
  名称：

  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

  摘要：

  DOI：
• 作为产物：
  描述：

  己二酸二乙酯 在 盐酸 、 sodium ethanolate 、 potassium carbonate 作用下， 反应 23.0h， 生成 3-Methyl-cyclopentan-2-one-1-acetic acid
  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

• Bradfield et al., Journal of the Chemical Society, 1936, p. 1619,1624
  作者：Bradfield et al.

  DOI：——

  日期：——
• Chatterjee, D. N.; Sarkar, Malati, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 968 - 969
  作者：Chatterjee, D. N.、Sarkar, Malati

  DOI：——

  日期：——
• RAO, R. R.;SARKAR, RINA;BHATTACHARYA, SUKLA;MUKHERJEE, M. N., INDIAN J. CHEM., 26,(1987) N 10, 939-946
  作者：RAO, R. R.、SARKAR, RINA、BHATTACHARYA, SUKLA、MUKHERJEE, M. N.

  DOI：——

  日期：——
• CHATTERJEE D. N.; SARKAR MALATI, INDIAN J. CHEM., 24,(1985) N 9, 968-969
  作者：CHATTERJEE D. N.、 SARKAR MALATI

  DOI：——

  日期：——
• SUBSTITUTED 1,2,3,4-TETRAHYDROCYCLOPENTA[b]INDOL-3-YL)ACETIC ACID DERIVATIVES USEFUL IN THE TREATMENT OF AUTOIMMUNE AND INFLAMMATORY DISORDERS
  申请人：Arena Pharmaceuticals, Inc.

  公开号：US20170217885A1

  公开（公告）日：2017-08-03

  The present invention relates to certain substituted 1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid derivatives of Formula (Ia) and pharmaceutically acceptable salts thereof, which exhibit useful pharmacological properties, for example, as agonists of the S1P1 receptor. Also provided by the present invention are pharmaceutical compositions containing compounds of the invention, and methods of using the compounds and compositions of the invention in the treatment of S1P1 receptor-associated disorders, for example, psoriasis, rheumatoid arthritis, Crohn's disease, transplant rejection, multiple sclerosis, systemic lupus erythematosus, ulcerative colitis, type I diabetes, acne, microbial infections or diseases and viral infections or diseases.