(1R,3R)-cyclopent-4-ene-1,3-diol | 61348-02-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3R)-cyclopent-4-ene-1,3-diol
• 英文别名: (1R,3R)-4-cyclopentene-1,3-diol；trans-Cyclopenten-diol-(3,5)；trans-4-Cyclopenten-1,3-diol；trans-3,5-Dihydroxycyclopent-1-ene
• CAS: 61348-02-5
• 化学式: C₅H₈O₂
• 分子量: 100.117
• InChiKey: IGRLIBJHDBWKNA-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,3R)-cyclopent-4-ene-1,3-diol 、 tert-butyl (2S)-2-isocyanato-3-phenylpropanoate 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以66%的产率得到(1R,3R)-cyclopent-4-ene-1,3-diyl-bis(tert-butyl-L-phenylalaninate)carbamate
  参考文献：
  名称：

  Synthesis of cyclic 1,3-diols as scaffolds for spatially directed libraries

  摘要：

  一系列1,3-二醇已经合成并用于创建一个空间多样化化合物的试验库。

  DOI：

  10.1039/c6ob00598e
• 作为产物：
  描述：

  2,4-戊二酮,1,5-二氯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 正丁基锂 、 [(S)-2,2'-双(二苯基磷)-1,1'-联萘]二氯化钌(II) 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (1R,3R)-cyclopent-4-ene-1,3-diol
  参考文献：
  名称：

  Stereodivergent Synthesis of Enantioenriched 4-Hydroxy-2-cyclopentenones

  摘要：

  Protected 4-hydroxycyclopentenones (4-HCPs) constitute an important class of intermediates in chemical synthesis. A route to this class of compound has been developed. Key steps include Noyori reduction (which establishes the stereochemistry of the product), ring-closing metathesis, and simple functional group conversions to provide a set of substituted 4-HCPs in either enantiomeric form.

  DOI：

  10.1021/jo402539p

文献信息

• Chiral Preparation of C2-Symmetric 4-Cyclopentene-1,3-diol
  作者：Seiko Kimura、Ryoko Ehama、Kohei Inomata

  DOI：10.1055/s-2002-31949

  日期：——

  Optically pure C2 -symmetric 4-cyclopentene-1,3-diol has been prepared in both enantiomeric forms from racemic (3aS*,4R*,7S*,7aS*)-3a,4,7,7a-tetrahydro-4,7-methano-1H-inden-1-one by employing lipase-mediated kinetic resolution as the key step. As a result, the known (3aS*,4R*,7S*,7aS*)-3a,4,7,7a-tetrahydro-4,7-methano-1H-inden-1-one is transformed into (1′S*,3′S*,3′aR*,4′S*,7′R*,7′aS*)- 2′,3′,3′a,4′,7′,7′a-hexahydro-3′-hydroxy-4′,7′-methano-1′H-inden-1′-yl benzoate, via stereo- and regioselective hydride reduction of epoxy ketone and sequential benzoylation, which is resolved under transesterification conditions in the presence of lipase. The hydride reduction of benzoate and acetate gives the corresponding chiral diols, which are further transformed into both enantiomers of C2 -symmetric 4-cyclopentene-1,3-diol via a retro-Diels-Alder reaction.

  通过脂肪酶介导的动力学解析这一关键步骤，从外消旋(3aS*,4R*,7S*,7aS*)-3a,4,7,7a-四氢-4,7-甲桥-1H-茚-1-酮制备出了两种对映体形式的光学纯 C2-不对称 4-环戊烯-1,3-二醇。结果，已知的 (3aS*,4R*,7S*,7aS*)-3a,4,7,7a-四氢-4,7-甲桥-1H-茚-1-酮转化为 (1′S*,3′S*,3′aR*,4′S*,7′R*,7′aS*)-2′,3′,3′a,4′,7′,7′a-六氢-3′-羟基-4′、7′-甲桥-1′H-茚-1′-基苯甲酸酯，通过环氧酮的立体和区域选择性氢化物还原和顺序苯甲酰化，在脂肪酶存在下的酯交换条件下进行。苯甲酸酯和乙酸酯的氢化物还原反应产生了相应的手性二元醇，通过逆-Diels-Alder 反应，这些手性二元醇进一步转化为 C2-不对称 4-环戊烯-1,3-二醇的两种对映体。
• Process for the preparation of 4-hydroxycyclopent-2-en-1-one derivatives
  申请人：Teijin Limited

  公开号：US04132726A1

  公开（公告）日：1979-01-02

  Novel optically active compounds of 4-protected hydroxy-cyclopent-2-en-1-ones of the formula ##STR1## wherein R is a splittable protective group for an alcoholic hydroxyl group, and a process for preparing the 4-protected hydroxycyclopent-2-en-1-ones by oxidizing monohydroxy-protected derivatives of cyclopent-1-ene-3,5-diol expressed by the following formula ##STR2## wherein R is the same as defined above. Optically active 4-hydroxycyclopent-2-en-1-one which is an optically active isomer of the compound of formula (2); or optically active cyclopent-1-en-3,5-diol (R-isomer) and a novel diacyl derivative of the diol, a novel monoacylmonosilyl-derivative of the diol and a novel monoacylmonotetrahydropyranol-derivative of the diol, which are intermediates for the protective derivative of formula (1). Processes are also provided for preparing the protective derivatives of formula (1) by converting these intermediates by esterification, hydrolysis, enzymatic processes, etc. The optically active compounds of formula (2) are useful as precursors for the preparation of prostaglandin or its analogues.

  本发明涉及一种4-保护羟基环戊-2-烯-1-酮的光学活性化合物，其化学式为##STR1##其中R是可分离的羟基保护基团，并提供了一种制备4-保护羟基环戊-2-烯-1-酮的方法，通过氧化以下化学式所示的环戊-1-烯-3,5-二醇的单羟基保护衍生物来实现：##STR2##其中R与上述定义相同。本发明还涉及一种光学活性的4-羟基环戊-2-烯-1-酮，它是化合物式（2）的光学异构体；或者光学活性的环戊-1-烯-3,5-二醇（R-异构体）以及一种新型的二酰基衍生物、一种新型的单酰基单硅烷基衍生物和一种新型的单酰基单四氢吡喃基衍生物，它们是化合物式（1）的保护衍生物的中间体。本发明还提供了通过酯化、水解、酶法等将这些中间体转化为化合物式（1）的保护衍生物的方法。化合物式（2）的光学活性化合物可用作前体，用于制备前列腺素或其类似物。
• XRISTOFOROV, V. L.;FIXTE, B. B.;SEREBRYANYJ, V. A.;VOLKOVA, O. B.;FILIPPO+, SINTEZ I ISSLED. PROSTAGLANDINOV, MINSK,(1989) S. 74
  作者：XRISTOFOROV, V. L.、FIXTE, B. B.、SEREBRYANYJ, V. A.、VOLKOVA, O. B.、FILIPPO+

  DOI：——

  日期：——
• VALPEY, R. S.;MILLER, D. J.;ESTES, J. M.;GODLESKI, S. A., J. ORG. CHEM., 1982, 47, N 24, 4717-4720
  作者：VALPEY, R. S.、MILLER, D. J.、ESTES, J. M.、GODLESKI, S. A.

  DOI：——

  日期：——
• KWIATKOWSKI, STEFAN;LANGWALD, MARIA
  作者：KWIATKOWSKI, STEFAN、LANGWALD, MARIA

  DOI：——

  日期：——