5-carbomethoxymethyl-5-methyloxycyclopentan-2-one | 98558-82-8

• 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: 5-carbomethoxymethyl-5-methyloxycyclopentan-2-one
• 英文别名: (2-methyl-5-oxo-tetrahydro-[2]furyl)-acetic acid methyl ester；(2-Methyl-5-oxo-tetrahydro-[2]furyl)-essigsaeure-methylester；Methyl 2-(2-methyl-5-oxooxolan-2-yl)acetate
• CAS: 98558-82-8
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: YBONZTCKXPZVAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-carbomethoxymethyl-5-methyloxycyclopentan-2-one 在 甲醇 、 sodium methylate 作用下， 生成 (E)-4-methyl-6-hydroxy-4-hexenoic acid
  参考文献：
  名称：

  Elvidge et al., Journal of the Chemical Society, 1951, p. 3386,3393,3397

  摘要：

  DOI：
• 作为产物：
  描述：

  (2-methyl-5-oxo-2,5-dihydrofuran-2-yl)acetic acid methyl ester 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 反应 4.5h， 以90%的产率得到5-carbomethoxymethyl-5-methyloxycyclopentan-2-one
  参考文献：
  名称：

  Piperonal as Starting Material for the Regiospecific and Stereoselective Synthesis ofEandZIsomers of 3-Methyl-2-hexenedioic acid-1-methyl ester

  摘要：

  A short synthesis of gamma-lactone 5 was developed starting from the easily available piperonal 1. The key step in this approach was an ozonation of the aromatic ring of 2. Compound 5 led stereoselectively to 6 or 7 by a beta-elimination reaction under thermo-dynamic or kinetic conditions.

  DOI：

  10.1080/00397919108020839

文献信息

• METHOD OF PRODUCING ALPHA,BETA-UNSATURATED DICARBOXYLIC ACID ESTER
  申请人：Toray Industries, Inc.

  公开号：US20220162148A1

  公开（公告）日：2022-05-26

  A method of producing an α,β-unsaturated dicarboxylic acid ester exemplified by an α-hydromuconic acid ester from a carboxylic acid ester exemplified by a 3-hydroxyadipic acid ester or a 3-hydroxyadipic acid-3,6-lactone ester, in which the selectivity for the α,β-unsaturated dicarboxylic acid ester can be increased by subjecting the carboxylic acid ester to a basic condition of pH 8.5 to less than 13 in an organic solvent or a mixed solvent of an organic solvent and water.

  一种制备α，β-不饱和二羧酸酯的方法，以α-羟基须二酸酯为例，从羧酸酯（例如3-羟基己二酸酯或3-羟基己二酸-3,6-内酯酯）制备而来。在有机溶剂或有机溶剂和水的混合溶剂中，将羧酸酯置于pH 8.5至小于13的碱性条件下，可以提高α，β-不饱和二羧酸酯的选择性。
• METHOD FOR PRODUCING ?,?-UNSATURATED DICARBOXYLIC ACID ESTER
  申请人：Toray Industries, Inc.

  公开号：EP3932900A1

  公开（公告）日：2022-01-05

  In a method for producing an α,β-unsaturated dicarboxylic acid ester exemplified by an α-hydromuconic acid ester from a carboxylic acid ester exemplified by a 3-hydroxyadipic acid ester or a 3-hydroxyadipic acid-3,6-lactone ester, the selectivity for the α,β-unsaturated dicarboxylic acid ester can be raised by subjecting the carboxylic acid ester to a basic condition of pH 8.5 to less than 13 in an organic solvent or a mixed solvent of an organic solvent and water.

  在从以 3-羟基己二酸酯或 3-羟基己二酸-3,6-内酯为例的羧酸酯生产α,β-不饱和二羧酸酯的方法中，可通过将羧酸酯置于 pH 值为 8.5至小于13的碱性条件下，在有机溶剂或有机溶剂与水的混合溶剂中进行反应。
• Elvidge et al., Journal of the Chemical Society, 1951, p. 3386,3393,3397
  作者：Elvidge et al.

  DOI：——

  日期：——
• The absolute configuration of peroxisomicines A1 and A2
  作者：Alejandro Pérez、Rosalba Ramírez-Durón、Alfredo Piñeyro-López、Noemí Waksman、Matthias Reichert、Gerhard Bringmann

  DOI：10.1016/j.tet.2004.06.123

  日期：2004.9

  Peroxisomicine A1 is a potentially antineoplastic compound isolated from the seeds of Karwinskia parvifolia. It is considered as a useful chemotype for the preparation of topoisomerase II targeted anticancer cells. Stereochemically, it is characterized by the presence of two stereocenters and a rotationally hindered and thus likewise stereogenic biaryl axis. In this contribution, the absolute configuration of peroxisomicine A1 and its epimer, peroxisomicine A2, was established by means of a five-step degradative procedure giving the respective R- and S-configured methyl 2-(2'-methyl-5'-oxotetrahydrofuryl)acetates. The configuration of the degradation product was obtained by means of optical rotation, H-1 NMR analysis using a chiral displacement reagent, and by experimental and quantum chemical circular dichroism (CD) investigations. Based on the results obtained here and considering our previous work on the relative configuration at centers versus axis of these compounds, peroxisomicine A1 resulted to be the P,3S,3'S-isomer and peroxisomicine A2 the P,3R,3'S-isomer. (C) 2004 Elsevier Ltd. All rights reserved.
• PINHEIRO, SERGIO;CASTRO, ROSANE N.;FERNANDES, MARIA F. G.;COSTA, PAULO R.+, SYNTH. COMMUN., 21,(1991) N, C. 703-712
  作者：PINHEIRO, SERGIO、CASTRO, ROSANE N.、FERNANDES, MARIA F. G.、COSTA, PAULO R.+

  DOI：——

  日期：——