(+/-)-3-dimethoxymethyl-4-hydroxy-2-methoxycarbonylmethylcyclopent-2-en-1-one | 102865-10-1

• 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: (+/-)-3-dimethoxymethyl-4-hydroxy-2-methoxycarbonylmethylcyclopent-2-en-1-one
• 英文别名: 4-hydroxy-3-dimethoxymethyl-2-methoxycarbonylmethyl-2-cyclopentene-1-one；Methyl 2-[2-(dimethoxymethyl)-3-hydroxy-5-oxocyclopenten-1-yl]acetate
• CAS: 102865-10-1
• 化学式: C₁₁H₁₆O₆
• 分子量: 244.244
• InChiKey: OXGZTBBBWCPDEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-3-dimethoxymethyl-4-hydroxy-2-methoxycarbonylmethylcyclopent-2-en-1-one 在 palladium on activated charcoal 咪唑 、 氢气 作用下， 以 甲醇 为溶剂， 反应 13.5h， 生成 (+/-)-3β-dimethoxymethyl-2β-methoxycarbonylmethyl-4-cyclopentane-1-one
  参考文献：
  名称：

  Stereochemical aspects of catalytic hydrogenation of 2,3-di- and 2,3,4-tri-substituted 2-cyclopentene-1-ones and reactivity of the resulting cyclopentanones

  摘要：

  DOI：

  10.1016/s0040-4020(01)85900-7
• 作为产物：
  描述：

  2-formyl-5-(2-methoxycarbonylethyl)furan 在 disodium hydrogenphosphate 、 水合氯醛 、 溴 、 sodium carbonate 、 对甲苯磺酸 、 三乙胺 、 APTS 、 柠檬酸 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 生成 (+/-)-3-dimethoxymethyl-4-hydroxy-2-methoxycarbonylmethylcyclopent-2-en-1-one
  参考文献：
  名称：

  Enzymatic kinetic resolution of a functionalized 4-hydroxy-cyclopentenone: synthesis of the key intermediates in the total synthesis of isoprostanes

  摘要：

  The enzymatic kinetic resolution of racemic alcohol 4-hydroxy-cyclopentenone 1 was investigated using four different lipases for enantioselective transacetylation, as well as for enantioselective hydrolysis, leading to the pure (R)- and (S)-enantiomers 2 and 3. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.028

文献信息

• Total Synthesis of the Four Enantiomerically Pure Diasteroisomers of the Phytoprostanes E₁Type II and of the 15-E_2t-Isoprostanes
  作者：Edith Pinot、Alexandre Guy、Anais Fournial、Laurence Balas、Jean-Claude Rossi、Thierry Durand

  DOI：10.1021/jo702455g

  日期：2008.4.1

  Syntheses of the four enantiomerically pure diastereoisomers of the phytoprostanes E1 type II and 15-E2t-isoprostanes (1−4) are described. The key steps included the preparation of the Freïmanis (±)-hydroxycyclopentenone 5, enzymatic resolution of this racemic hydroxycyclopentenone, Wittig and Horner−Wadsworth−Emmons (HWE) coupling reactions and finally enantioselective reductions.

  所述phytoprostanes的四个对映体纯非对映体的合成ë 1 II型和15-E 2吨-isoprostanes（1 - 4）中有所描述。关键步骤包括弗雷曼尼斯（±）-羟基环戊烯酮5的制备，该外消旋羟基环戊烯酮的酶促拆分，Wittig和Horner-Wadsworth-Emmons（HWE）偶联反应，最后是对映选择性还原。
• LOZHA, EH. V.;LOLYA, D. O.;FREJMANIS, YA. F.;TUROVSKIJ, I. V.;GAVARS, M. +, IZV. AN LATVSSR. CEP. XIM., 1985, N 4, 465-472
  作者：LOZHA, EH. V.、LOLYA, D. O.、FREJMANIS, YA. F.、TUROVSKIJ, I. V.、GAVARS, M. +

  DOI：——

  日期：——
• LOZA, E.;LOLA, D.;FREIMANIS, J.;TUROVSKIS, I.;ROZITE, S.;BOKALDERE, R.;SA+, TETRAHEDRON, 44,(1988) N 4, 1207-1219
  作者：LOZA, E.、LOLA, D.、FREIMANIS, J.、TUROVSKIS, I.、ROZITE, S.、BOKALDERE, R.、SA+

  DOI：——

  日期：——
• Stereochemical aspects of catalytic hydrogenation of 2,3-di- and 2,3,4-tri-substituted 2-cyclopentene-1-ones and reactivity of the resulting cyclopentanones
  作者：E. Loža、D. Loļa、J. Freimanis、I. Turovskis、S. Rozíte、R. Bokaldere、O. Sahartova

  DOI：10.1016/s0040-4020(01)85900-7

  日期：1988.1
• Enzymatic kinetic resolution of a functionalized 4-hydroxy-cyclopentenone: synthesis of the key intermediates in the total synthesis of isoprostanes
  作者：Edith Pinot、Alexandre Guy、Ann-Laure Guyon、Jean-Claude Rossi、Thierry Durand

  DOI：10.1016/j.tetasy.2005.03.028

  日期：2005.6

  The enzymatic kinetic resolution of racemic alcohol 4-hydroxy-cyclopentenone 1 was investigated using four different lipases for enantioselective transacetylation, as well as for enantioselective hydrolysis, leading to the pure (R)- and (S)-enantiomers 2 and 3. (c) 2005 Elsevier Ltd. All rights reserved.