3-(3(S)-hydroxy-5-oxo-1-cyclopent-1-yl)propyne | 86247-53-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3(S)-hydroxy-5-oxo-1-cyclopent-1-yl)propyne
• 英文别名: 4(S)-hydroxy-2-propargyl-2-cyclopentenone；(4S)-4-hydroxy-2-prop-2-ynylcyclopent-2-en-1-one
• CAS: 86247-53-2
• 化学式: C₈H₈O₂
• 分子量: 136.15
• InChiKey: QGZRURGVDVUAJB-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4-Oxo-3-prop-2-ynylcyclopent-2-en-1-yl) acetate 生成 3-(3(S)-hydroxy-5-oxo-1-cyclopent-1-yl)propyne
  参考文献：
  名称：

  MINAMII, MASAESI;UEHDA, YUDZI

  摘要：

  DOI：

文献信息

• Process for preparing optically active 4-hydroxy-2-cyclipentenones
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0153653A1

  公开（公告）日：1985-09-04

  A process for preparing an optically active 2-substituted or unsubstituted-4-hydroxy-2-cyclopentenone of the formula. wherein R is a hydrogen atom, an allyl group or a propargyl group, which comprises reacting the corresponding 2- substituted or unsubstituted-4-hydroxy-2-cyclopentenone of the formula: wherein R is defined above with a lactone chosen from (1R,5S)-6,6-Edimethyl-4-hydroxy-3-oxabicycto(3.1.0]hexan-2- one or (1S,5R)-6,6-dimethyl-4-hydroxy-3-oxabicyclo[3.1.0]-hexan-2-one in a molar ratio of 1.5 - 2 : 1 in the presence of p-toluenesulfonic acid or benzenesulfonic acid in the coexistence of an organic solvent under elimination of water as an azeotropic mixture with the organic solvent to obtain a reaction mixture comprising (1R,5S)-6,6-dimethyl-3-oxa-4(R)-[1(R)-4-oxo-2-substituted or unsubstituted-2-cyclo- pentenyloxy]bicyclo[3.1.0]hexan-2-one or (1S,5R)-6,6-dimethyl-3-oxa-4(S)-[1(S)-4-oxo-2-substituted or unsubstituted-2-cyclopentenyloxy]bicyclo[3.1.0]hexan-2-one of the formula: wherein R is as defined above, of which either one isomer is contained in a considerably larger amount than the other isomer, separating the isomer having the larger content from the reaction mixture and hydrolyzing the separated isomer to give the optically active 2-substituted or unsubstituted-4-hydroxy-2-cyclopentenone.

  一种制备具有光学活性的式 2-取代或未取代-4-羟基-2-环戊烯酮的工艺。 其中 R 为氢原子、烯丙基或丙炔基，该工艺包括将相应的式 2-取代或未取代-4-羟基-2-环戊烯酮与选自(1R,5S)、(1R,5S)和(1R,5S)的内酯反应： 其中 R 如上定义，与选自 (1R,5S)-6,6-二甲基-4-羟基-3-氧杂双环[3.1.0]己烷-2-酮或 (1S,5R)-6,6-二甲基-4-羟基-3-氧杂双环[3.1.0]己烷-2-酮的内酯在摩尔比为 1.5 - 2 : 1 的对甲苯磺酸或苯磺酸存在下，在有机溶剂的共沸混合物中消除水，得到包含 (1R,5S)-6,6-二甲基-3-氧杂-4(R)-[1(R)-4-氧代-2-取代或未取代-2-环戊烯氧基]双环[3.1.0]己-2-酮或式(1S,5R)-6,6-二甲基-3-氧杂-4(S)-[1(S)-4-氧代-2-取代或未取代-2-环戊烯氧基]双环[3.1.0]己-2-酮： 其中 R 如上文所定义，其中一种异构体的含量大大高于另一种异构体，从反应混合物中分离出含量较高的异构体，水解分离出的异构体，得到光学活性的 2-取代或未取代-4-羟基-2-环戊烯酮。
• Method of resolution of hydroxy-cyclopentenones using a lipase and transacylation agents
  申请人：G.D. Searle & Co.

  公开号：EP0357009A2

  公开（公告）日：1990-03-07

  A process for irreversible regio- and stereoselective enzyme catalyzed acylation of alcohols using enol esters as acylating reagents is disclosed. The present invention permits the selective modification of hydroxyl group(s) of chiral and meso alcohols, including sugars, organometallics, and glycosides. The enol freed upon transesterification rapidly tautomerizes to the corresponding volatile aldehyde or ketone thereby preventing the reverse reaction from occurring.

  本发明公开了一种使用烯醇酯作为酰化试剂的不可逆区域和立体选择性酶催化醇酰化工艺。本发明可以选择性地修饰手性醇和中性醇（包括糖、有机金属和苷类）的羟基。酯交换反应后释放出的烯醇会迅速同分异构成相应的挥发性醛或酮，从而防止发生逆反应。
• Lipase-catalyzed irreversible transesterification using enol esters: resolution of prostaglandin synthons 4-hydroxy-2-alkyl-2-cyclopentenones and inversion of the 4S enantiomer to the 4R enantiomer
  作者：Kevin A. Babiak、John S. Ng、John H. Dygos、Cara L. Weyker、Yi Fong Wang、Chi Huey Wong

  DOI：10.1021/jo00297a073

  日期：1990.5
• MINAMII, MASAESI;UEHDA, YUDZI
  作者：MINAMII, MASAESI、UEHDA, YUDZI

  DOI：——

  日期：——
• BABIAK, KEVIN A.;NG, JOHN S.;DYGOS, JOHN H.;WEYKER, CARA L.;WANG, YI-FONG+, J. ORG. CHEM., 55,(1990) N0, C. 3377-3381
  作者：BABIAK, KEVIN A.、NG, JOHN S.、DYGOS, JOHN H.、WEYKER, CARA L.、WANG, YI-FONG+

  DOI：——

  日期：——