(1S,4R)-(-)-4-Hydroxycyclopent-2-enyl butanoate | 130792-54-0

• 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: (1S,4R)-(-)-4-Hydroxycyclopent-2-enyl butanoate
• 英文别名: [(1S,4R)-4-hydroxycyclopent-2-en-1-yl] butanoate
• CAS: 130792-54-0
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: NLFMWTUWKKWNIG-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (1S,4R)-(-)-4-Hydroxycyclopent-2-enyl butanoate 在 Wofatit SPW (OH form) 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (1S,4R)-(+)-4-(Tetrahydro-2-pyranyloxy)cyclopent-2-enol
  参考文献：
  名称：

  Theil, Fritz; Schick, Hans; Lapitskaya, Margarita A., Liebigs Annalen der Chemie, 1991, # 3, p. 195 - 200

  摘要：

  DOI：
• 作为产物：
  描述：

  (4-Butanoyloxycyclopent-2-en-1-yl) butanoate 以62%的产率得到
  参考文献：
  名称：

  Dols Paul P. M. A., Klunder Antonius J. H., Zwanenburg Binne, Tetrahedron, 50 (1994) N 28, S 8515-8538

  摘要：

  DOI：

文献信息

• Chemoenzymatic routes to cyclopentenols: the role of protecting groups on stereo- and enantioselectivity
  作者：Simon Specklin、Anna Dikova、Aurélien Blanc、Jean-Marc Weibel、Patrick Pale

  DOI：10.1016/j.tetlet.2014.10.105

  日期：2014.12

  lyloxycyclopent-2-en-1-one was very efficiently obtained from diacetate of cis-cyclopent-2-en-1,3-diol using enzymatic desymmetrization with CAL-B. In these sequences, TIPS proved to be the best protecting group.

  对映体（R）-4-三异丙基甲硅烷氧基环戊-2-烯-1-酮是通过短序列获得的，这些短序列包括外消旋顺式-4-三异丙基甲硅烷氧基环戊-2-烯-1-醇的酶促拆分或顺式-环戊基-的酶促脱对称化。2-en-1,3-二醇。另外，对映体（S）-4-三异丙基甲硅烷基氧基环戊-2-烯-1-酮可以通过用CAL-B酶促脱对称从顺式-环戊-2-烯-1,3-二醇的二乙酸酯中非常有效地获得。在这些序列中，TIPS被证明是最佳的保护基团。
• Chiral induction in cyclopentyl-derived 1,3-meso-diesters: enantioselective hydrolyses with electric eel acetylcholinesterase
  作者：Donald R Deardorff、Roberto B Amador、James W Morton、Henry Y Kim、Cullen M Taniguchi、Arnel A Balbuena、Sam A Warren、Vadim Fanous、S.W.Tina Choe

  DOI：10.1016/s0957-4166(99)00236-0

  日期：1999.6

  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.
• 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：——