3-hydroxy-8-nonene-2,5-dione | 80350-56-7

• 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: 3-hydroxy-8-nonene-2,5-dione
• 英文别名: 3-hydroxy-non-8-ene-2,5-dione；3-Hydroxy-non-8-en-2,5-dion；Nonen-(1)-ol-(7)-dion-(5.8)；3-Hydroxynon-8-ene-2,5-dione
• CAS: 80350-56-7
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: NKOPXXIKCMTWQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-8-nonene-2,5-dione 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-丙烯基-3-甲基-4-羟基-2-环戊烯-1-酮
  参考文献：
  名称：

  Farkas,J. et al., Collection of Czechoslovak Chemical Communications, 1960, vol. 25, p. 1824 - 1836

  摘要：

  DOI：
• 作为产物：
  描述：

  dimethyl 1-allyl-1,3-acetonedicarboxylate 在 氢氧化钾 作用下， 生成 3-hydroxy-8-nonene-2,5-dione
  参考文献：
  名称：

  Process for manufacture of 2, 5 diketo-8-nonen-3-ol

  摘要：

  该发明涉及一种单烯丙基丙酮二羧酸二酯、其自由酸及其碱金属和碱土金属盐。该酯可通过在无水条件下，在碱性缩合剂和惰性有机溶剂的存在下，将丙酮羧酸二酯与烯丙基卤化物反应而制备得到。反应可在升高的温度下进行，如果需要，还可在压力下进行。用作试剂的酯最好是碳原子数最多为5的酯，如甲基、乙基和丙基酯，而缩合剂适宜为碱金属醇盐。当使用烯丙基氯化物作为试剂时，最好过量使用。得到的烯丙基丙酮羧酸酯可用碱性碳酸钠或碱性地球金属化合物的水溶液皂化，例如氢氧化钠、碳酸钠或碳酸锂，以得到相应的烯丙基-丙酮二羧酸盐，可通过加入低级脂肪醇等方式进行分离。盐的水溶液可酸化以释放自由酸，然后通过丙酮萃取等方式进行回收。或者，盐的水溶液可在pH值为6.5至9.5的条件下与丙酮醛反应，形成相应的1-烯丙基-2,5-二酮-4-羟基庚酸盐，可通过与非溶剂如甲醇沉淀或在真空下冷冻状态下干燥溶液来分离。自由酸可通过将盐的水溶液冷却至接近其冰点，加入稀酸并搅拌，然后通过冷冻干燥酸化溶液来获得。自由酸在室温下脱羧成为非-8-烯-2,5-二酮-3-醇，可通过与稀碱环化为烯丙内酮。通过将庚酸金属盐的水溶液酸化至pH值约为1.0-2.5，然后在中性水溶性溶剂的存在下，用水不相溶的溶剂进行萃取，即可直接得到无环酮醇。在实例中：（1）烯丙基溴在甲醇溶液中与丙酮羧酸二甲酯和甲醇钠在回流下反应，得到单烯丙基二甲基丙酮二羧酸酯；然后将酯皂化为氢氧化钾，用硫酸中和产物，加入丙酮醛，将pH值调整为7.5-8.0，在室温下搅拌混合物；得到的1-烯丙基-2,5-二酮-4-羟基庚酸钠盐水溶液用HCl酸化至pH2，放出CO2；得到非-8-烯-2,5-二酮-3-醇。 （2）烯丙基氯（3摩尔比例）在甲醇溶液中与丙酮羧酸二甲酯和甲醇钠反应，如（1）所述，以得到二甲基单烯丙基丙酮二羧酸酯。

  公开号：

  US02768967A1

文献信息

• A Novel Catechol Compound, an Unusual Side Reaction Product of a β-Ketoester with Pyruvic Aldehyde and Its Inhibition by Sodium Dithionite
  作者：Takeaki Kato、Masao Mochizuki、Shigeru Okano、Noritada Matsuo

  DOI：10.1081/scc-120026323

  日期：2003.12

  Abstract The structure of an usual catechol byproduct in the aldol condensation of the salt of 3-oxo-6-heptenoate and pyruvic aldehyde, and the discovery of an additive to inhibit its formation are described.

  摘要 描述了 3-oxo-6-heptenoate 和丙酮醛的盐的羟醛缩合中常见儿茶酚副产物的结构，以及抑制其形成的添加剂的发现。
• Andersen, Soeren H.; Das, Nalin B.; Joergensen, Ruth D., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1982, vol. 36, # 1, p. 1 - 14
  作者：Andersen, Soeren H.、Das, Nalin B.、Joergensen, Ruth D.、Kjeldsen, Gunhild、Knudsen, Jes S.、et al.

  DOI：——

  日期：——
• Schechter; Green; La Forge, Journal of the American Chemical Society, 1949, vol. 71, p. 3168
  作者：Schechter、Green、La Forge

  DOI：——

  日期：——
• Effects of 2% Ibopamine on Pupil, Refraction, Anterior Segment Anatomy and Intraocular Pressure
  作者：Giorgio Marchini、Silvia Babighian、Roberto Tosi、Sergio Perfetti、Luciano Bonomi

  DOI：10.1089/108076801750295254

  日期：2001.6

  The aim of the study was to determine the effects of a dopaminergic drug, 2% ibopamine, on the pupil, intraocular pressure and other ocular and ultrasound biometric variables.Thirty healthy subjects and 15 patients with primary open-angle glaucoma, aged from 40 to 78 years (mean age: 59.2 +/- 11), were included in two prospective open controlled trials. In the first, the mydriatic effect of 2% ibopamine and its inhibition and reversibility were evaluated in 15 healthy subjects using the alpha(1)-adrenergic drug, 0.5% dapiprazole. In the second, refraction, visual acuity, pupil diameter, intraocular pressure and 5 A-scan ultrasound biometric variables were evaluated in 15 healthy subjects and in 15 glaucoma patients.As early as forty min after administration of 2% ibopamine, a marked mydriatic ef feet (7.3 vs 3.9 mm; P < 0.0001), which was completely inhibited or reversed by 0.5% dapiprazole, was detected. The drug induced no changes in refraction, visual acuity or Ascan ultrasound biometric variables in any of the subjects examined. In healthy subjects, the intraocular pressure values were not changed to a statistically significant extent (13.8 vs 14.8 mm HE; P = 0.668), whereas a slight, though significant, hypertensive effect (24 vs 22.2 mm Hg, P = 0.002) was observed in the glaucoma patients.The study confirms the intense mydriatic effect of 2% ibopamine with no changes in refraction, visual acuity or A-scan ultrasound biometric variables, The drug has no effect on intraocular pressure in healthy subjects, but induces a significant hypertensive effect in patients with initial glaucoma. This characteristic could be used for early diagnosis of primary open-angle glaucoma.
• AKITA, KOITI
  作者：AKITA, KOITI

  DOI：——

  日期：——