(1R,4S)-(+)-4-hydroxycyclopent-2-enyl propionate | 247595-17-1

• 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: (1R,4S)-(+)-4-hydroxycyclopent-2-enyl propionate
• 英文别名: [(1R,4S)-4-hydroxycyclopent-2-en-1-yl] propanoate
• CAS: 247595-17-1
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: HCYYWWWVLDNESR-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,4S)-(+)-4-hydroxycyclopent-2-enyl propionate 、 丙酸酐 在 吡啶 作用下， 反应 24.0h， 以74%的产率得到cis-Cyclopent-2-ene-1,4-diyl dipropanoate
  参考文献：
  名称：

  Chiral induction in cyclopentyl-derived 1,3-meso-diesters: enantioselective hydrolyses with electric eel acetylcholinesterase

  摘要：

  Eight 1,3-meso-diesters derived from a common cyclopentyl backbone were exposed to the hydrolase enzyme acetylcholinesterase from Electrophorus electricus. All eight compounds were hydrolyzed by the enzyme. The overall enantioselectivities were quite high, and the resulting e.e.s were generally >90%. The absolute configurations of the product monoesters were determined through stereochemical correlation. These data revealed that the preferred site for enzymatic hydrolysis in seven of the substrates was the pro-S ester function, with pro-R cleavage detected in the eighth. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00236-0
• 作为产物：
  描述：

  6-噁双环[3.1.0]-3-己烯 在 吡啶 、 sodium dihydrogenphosphate 、 四(三苯基膦)钯 、 sodium azide 、 Electrophorus electricus acetylcholinesterase 作用下， 以 四氢呋喃 为溶剂， 反应 24.25h， 生成 (1R,4S)-(+)-4-hydroxycyclopent-2-enyl propionate
  参考文献：
  名称：

  Chiral induction in cyclopentyl-derived 1,3-meso-diesters: enantioselective hydrolyses with electric eel acetylcholinesterase

  摘要：

  Eight 1,3-meso-diesters derived from a common cyclopentyl backbone were exposed to the hydrolase enzyme acetylcholinesterase from Electrophorus electricus. All eight compounds were hydrolyzed by the enzyme. The overall enantioselectivities were quite high, and the resulting e.e.s were generally >90%. The absolute configurations of the product monoesters were determined through stereochemical correlation. These data revealed that the preferred site for enzymatic hydrolysis in seven of the substrates was the pro-S ester function, with pro-R cleavage detected in the eighth. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00236-0

文献信息

• Theil, Fritz; Schick, Hans; Lapitskaya, Margarita A., Liebigs Annalen der Chemie, 1991, # 3, p. 195 - 200
  作者：Theil, Fritz、Schick, Hans、Lapitskaya, Margarita A.、Pivnitsky, Kasimir K.

  DOI：——

  日期：——
• Enzymatic hydrolysis of prochiral -1,4-diacyl-2-cyc-lopentenediols: preparation of (1,4)-and (1,4)-4-hydroxy-2-cyclopentenylderivatives, versatile building blocks for cyclopentanoid natural products.
  作者：Kurt Laumen、Manfred Schneider

  DOI：10.1016/s0040-4039(01)81708-1

  日期：1984.1
• THEIL, FRITZ;SCHICK, HANS;LAPITSKAYA, MARGARITA A.;PIVNITSKY, KASIMIR K., LIEBIGS ANN. CHEM.,(1991) N, C. 195-200
  作者：THEIL, FRITZ、SCHICK, HANS、LAPITSKAYA, MARGARITA A.、PIVNITSKY, KASIMIR K.

  DOI：——

  日期：——