4-hydroxy-5-prop-2-enylcyclopent-2-en-1-one | 77806-58-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-5-prop-2-enylcyclopent-2-en-1-one
• 英文别名: 4-hydroxy-5-allyl-2-cyclopentenone；2-Allyl-3-hydroxy-4-cyclopentenone
• CAS: 77806-58-7
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: ONQGUUWSGZTDPO-UHFFFAOYSA-N

物化性质

• 沸点：
  260.6±39.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  2
• 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

• 作为反应物：
  描述：

  4-hydroxy-5-prop-2-enylcyclopent-2-en-1-one 在 三溴乙醛 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 21.0h， 以50%的产率得到2-allyl-4-hydroxycyclo-2-pentenone
  参考文献：
  名称：

  [EN] PROSTAGLANDIN SYNTHESIS
  [FR] SYNTHESE DE LA PROSTAGLANDINE

  摘要：

  公开号：

  WO2005058812A3
• 作为产物：
  描述：

  4-(2-呋喃基)-1-丁烯-4-醇 在 PPA 作用下， 以30%的产率得到4-hydroxy-5-prop-2-enylcyclopent-2-en-1-one
  参考文献：
  名称：

  Barker, Andrew J.; Pattenden, Gerald, Journal of the Chemical Society. Perkin transactions I, 1983, # 8, p. 1885 - 1891

  摘要：

  DOI：

文献信息

• Process for producing 4-hydroxycyclopentenones
  申请人：Sumitomo Chemical Company, Limited

  公开号：US04371711A1

  公开（公告）日：1983-02-01

  A method of producing a 4-hydroxycyclopentenone represented by the formula, ##STR1## wherein R.sub.1 is an alkyl, alkenyl, alkynyl, cycloalkyl, thienyl, phenyl, p-methylbenzyl or benzyl group and R.sub.2 is an alkyl, alkenyl or alkynyl group having 6 or less carbon atoms, which comprises reacting a furylcarbinol compound of the formula, ##STR2## wherein R.sub.1 is as defined above, in the presence of an acid in a mixed solvent of water and an organic solvent, to obtain a cyclopentenone compound of the formula, ##STR3## wherein R.sub.1 is as defined above; reacting the cyclopentenone compound in the presence of an oxidizing agent to obtain a cyclopentendione compound of the formula, ##STR4## wherein R.sub.1 is a defined above; reacting the cyclopentendione compound with a Grignard reagent of the formula, R.sub.2 MgX wherein R.sub.2 is as defined above and X is chlorine, bromine or iodine atom, to obtain an oxocyclopentene compound of the formula, ##STR5## wherein R.sub.1 and R.sub.2 are as defined above; and reacting the cyclopentenone compound in the presence of a base. The 4-hydroxycyclopentenones are useful intermediates of agricultural chemicals.

  生产4-羟基环戊烯酮的方法，其化学式表示为，其中R₁是烷基、烯基、炔基、环烷基、噻吩基、苯基、对甲基苯甲基或苄基，R₂是具有6个或更少碳原子的烷基、烯基或炔基，包括在水和有机溶剂的混合溶剂中，在酸的存在下将具有以下化学式的呋喃基醇化合物进行反应，其中R₁如上定义，以获得具有以下化学式的环戊烯酮化合物；在氧化剂的存在下将环戊烯酮化合物进行反应，以获得具有以下化学式的环戊二酮化合物，其中R₁如上定义；将环戊二酮化合物与具有以下化学式的格氏试剂R₂MgX进行反应，其中R₂如上定义，X为氯、溴或碘原子，以获得具有以下化学式的氧代环戊烯化合物，其中R₁和R₂如上定义；在碱的存在下将环戊烯酮化合物进行反应。4-羟基环戊烯酮是农药化学品的有用中间体。
• Cyclopentendione and cyclopentenone
  申请人：Sumitomo Chemical Company, Limited

  公开号：US04465862A1

  公开（公告）日：1984-08-14

  A method of producing a 4-hydroxycyclopentenone represented by the formula, ##STR1## wherein R.sub.1 is an alkyl, alkenyl, alkynyl, cycloalkyl, thienyl, phenyl, p-methylbenzyl or benzyl group and R.sub.2 is an alkyl, alkenyl or alkynyl group having 6 or less carbon atom, which comprises reacting a furylcarbinol compound of the formula, ##STR2## wherein R.sub.1 is as defined above, in the presence of an acid in a mixed solvent of water and an organic solvent, to obtain a cyclopentenone compound of the formula, ##STR3## wherein R.sub.1 is as defined above; reacting the cyclopentenone compound in the presence of an oxidizing agent to obtain a cyclopentendione compound of the formula, ##STR4## wherein R.sub.1 is as defined above; reacting the cyclopentendione compound with a Grignard reagent of the formula, R.sub.2 MgX wherein R.sub.2 is as defined above and X is chlorine, bromine or iodine atom, to obtain an oxocyclopentene compound of the formula, ##STR5## wherein R.sub.1 and R.sub.2 are as defined above; and reacting the cyclopentenone compound in the presence of a base. The 4-hydroxycyclopentenones are useful intermediates of agricultural chemicals.

  一种制备4-羟基环戊酮的方法，其化学式为##STR1##其中R.sub.1为烷基，烯基，炔基，环烷基，噻吩基，苯基，对甲基苄基或苄基基团，R.sub.2是具有6个或更少碳原子的烷基，烯基或炔基，包括在水和有机溶剂的混合溶剂中，在酸的存在下反应化合物##STR2##其中R.sub.1如上定义，以获得化合物##STR3##其中R.sub.1如上定义；在氧化剂的存在下反应环戊酮化合物以获得化合物##STR4##其中R.sub.1如上定义；将环戊二酮化合物与Grignard试剂反应，其化学式为R.sub.2MgX，其中R.sub.2如上定义，X为氯，溴或碘原子，以获得氧代环戊烯化合物，其化学式为##STR5##其中R.sub.1和R.sub.2如上定义；以及在碱的存在下反应环戊酮化合物。4-羟基环戊酮是农药化学品的有用中间体。
• Novel thiaprostaglandin E1 derivatives, process for production thereof, and pharmaceuticals containing these compounds
  申请人：TEIJIN LIMITED

  公开号：EP0051284A1

  公开（公告）日：1982-05-12

  A novel compound selected from the group consisting of 7-(or 6- or 4-) thiaprostaglandin E1 derivatives of the formula wherein A represents - in which n is 0,1 or 2, provided that only one A cut of three is (O)n ; R1- R7 and G are defined in claim 1, the 15-epimers of said thiaprostaglandin E1 derivatives, the enatiomers of said thiaprostaglandin E1 derivatives or their 15-epimers, and mixtures of these compounds, A 7-thiaprostagiandin E, derivatives and/or its optical isomer may be prepared by reacting a 2-organo-2-cyclopentenone (II) with an organic copper-lithium compound (III) to effect conjugation reaction. A 6-thiaprostaglandin E1 derivative and/or its optical isomer may be prepared by subjecting an α-β-unsaturated ketone (IV) and a thiol (V) to the Michael addition reaction. And 4-thiaprostaglandin derivative and/or its optical isomer may also be prepared by the Michael addition reaction from a 2-allyl substituted cyclopentanone (VI) and a thiol (VIII). Some compounds ((I)-1) amongst the compounds of the formula (I) and/or their optical isomer are useful for controlling vascularactions such as angina pectoris, vasodilation etc.

  选自由式 7-（或 6-或 4-）硫前列腺素 E1 衍生物组成的组的新型化合物 其中 A 代表 - 其中 n 为 0、1 或 2，条件是三个 A 中只有一个是 (O)n ;R1- R7和G在权利要求1中定义，所述硫前列腺素E1衍生物的15-表聚体，所述硫前列腺素E1衍生物的对映体或它们的15-表聚体，以及这些化合物的混合物、 7-硫前列腺素 E 衍生物和/或其光学异构体可通过 2-有机-2-环戊烯酮 (II) 与有机铜锂化合物 (III) 发生共轭反应来制备。6- 硫前列腺素 E1 衍生物和/或其光学异构体可通过使 α-β- 不饱和酮（IV）和硫醇（V）发生迈克尔加成反应来制备。4-硫代前列腺素衍生物和/或其光学异构体也可以由 2-烯丙基取代的环戊酮（VI）和硫醇（VIII）通过迈克尔加成反应制备。 式（I）化合物中的某些化合物（(I)-1）和/或其光学异构体可用于控制血管反应，如心绞痛、血管扩张等。
• SAJTO, KEHNDZI;YAMATIKA, JO
  作者：SAJTO, KEHNDZI、YAMATIKA, JO

  DOI：——

  日期：——
• SAITO, KENJI;YAMACHIKA, HIROSHI
  作者：SAITO, KENJI、YAMACHIKA, HIROSHI

  DOI：——

  日期：——