Ethyl 3-hydroxy-3-methylheptanoate | 36219-15-5

• 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: Ethyl 3-hydroxy-3-methylheptanoate
• 英文别名: 3-Hydroxy-3-methylheptansaeureethylester
• CAS: 36219-15-5
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: SUTRNTRVRLJORX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  Ethyl 3-hydroxy-3-methylheptanoate 在 吡啶 、 氢氧化钾 、 氯化亚砜 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 (3E)-3-Methyl-3-heptenoic acid
  参考文献：
  名称：

  Identification of sex pheromones from cowpea weevil,Callosobruchus maculatus, and related studies withC. analis (coleoptera: Bruchidae)

  摘要：

  Female cowpea weevils, Callosobruchus maculatus, produce a sex pheromone that elicits orientation and sexual behavior in males. Bioassay-directed isolation of the sex pheromone was conducted and compounds in the active fraction were identified and synthesized. Volatiles were collected from individual virgin females by adsorption on filter paper discs and hexane extraction. A bioassay was used in which the locomotory response of single males in glass vials was recorded upon exposure to treatments or controls. Crude extracts were subjected to silica gel column chromatography with solvents of increasing polarity; all activity eluted with methanol. Activity in the highly polar methanol fraction suggested a carboxylic acid or a compound with multiple polar functionality. Acid-base partitioning of the crude extract isolated all activity in the acid fraction, confirming that the pheromone was a carboxylic acid. The acid fraction was further fractionated by preparative GC with a Carbowax column. The most active GC fraction contained the following five 8-carbon acids identified by GC-MS and comparison with synthetic candidates: 3-methyleneheptanoic acid, (Z)-3-methyl-3-heptenoic acid, (E)-3-methyl-3-heptenoic acid, (Z)-3-methyl-2-heptenoic acid, and (E)-3-methyl-2-heptenoic acid. Each of the synthetic acids was active individually for males, and combinations of two or more of the acid pheromones had an additive effect. Upwind flight responses to natural and synthetic pheromones were observed in a flight tunnel. (Z)-3-Methyl-2-heptenoic acid was previously identified as the sex pheromone for the related C. analis, but this and the other four acid pheromones from C. maculatus were inactive for male C. analis. There was no cross-attraction between C. maculatus and C. analis in reciprocal studies using extracted volatiles from females of both species, GCMS analysis of C. analis female volatiles failed to detect any of the C. maculatus compounds but did find an unidentified C-8 acid with a GC retention time different from any of the C. maculatus pheromones.

  DOI：

  10.1007/bf02029543
• 作为产物：
  描述：

  三丁基硼 、 ethyl 3-hydroxycrotonate 以 苯 为溶剂， 生成 Ethyl 3-hydroxy-3-methylheptanoate
  参考文献：
  名称：

  三烷基硼烷与β-二羰基化合物的光化学反应

  摘要：

  DOI：

  10.1016/s0040-4039(01)84536-6

文献信息

• Synthesis and evaluation of a potent, well-balanced EP 2 /EP 3 dual agonist
  作者：Akihiro Kinoshita、Masato Higashino、Koji Yoshida、Yoshiyuki Aratani、Akito Kakuuchi、Keisuke Hanada、Hiroyuki Takeda、Atsushi Naganawa、Hidekazu Matsuya、Kazuyuki Ohmoto

  DOI：10.1016/j.bmc.2017.11.035

  日期：2018.1

  A highly potent and well-balanced dual agonist for the EP2 and EP3 receptors is described. Optimization of the lead compound was accomplished in consideration of the relative agonist activity against each EP subtype receptor and the pharmacokinetic profile. As the result, 2-[(2-(1R,2R)-2-[(1E,4S)-5-cyclopentyl-4-hydroxy-4-methyl-1-penten-1-yl]-5-oxocyclopentyl}eth-yl)thio]-1,3-thiazole-4-carboxylic acid (10) showed excellent potency (human EC50 EP2 = 1.1 nM, EP3 = 1.0 nM) with acceptable selectivity over the EP1 and EP4 subtypes (> 2000-fold). Further fine-tuning of compound 10 led to identification of ONO-8055 as a clinical candidate. ONO-8055 was effective at an extremely low dose (0.01 mg/kg, po, bid) in rats, and dose-dependently improved voiding dysfunction in a monkey model of underactive bladder (UAB). ONO-8055 is expected to be a novel and highly promising drug for UAB. (C) 2017 Elsevier Ltd. All rights reserved.
• [EN] NOVEL PROSTAGLANDIN INTERMEDIATES MODIFIED IN THE omega -CHAIN AND PROCESS FOR PREPARING SAME
  申请人：CHINOIN GYÓGYSZER ÉS VEGYÉSZETI TERMÉKEK GYÁRA RT.

  公开号：WO1988007537A1

  公开（公告）日：1988-10-06

  (EN) The invention relates to the preparation of compounds of formula (I), wherein R means a straight or branched chain C1-6 alkyl group optionally substituted by a cyclopentyl or cyclohexyl group; or a cyclopentyl or cyclohexyl group; and R1 stands for a C1-4 alkyl group. The invention relates also to the new intermediates of formula (II), formula (III), formula (IV) and formula (V).(FR) La présente invention se rapporte à la préparation de composés représentés par la formule (I), où R représente un groupe alkyle de 1 à 6 atomes de carbone à chaîne droite ou ramifiée, éventuellement substitué par un groupe cyclopentyle ou cyclohexyle; ou un groupe cyclopentyle ou cyclohexyle; et R1 représente un groupe alkyle de 1 à 4 atomes de carbone. La présente invention se rapporte également aux nouveaux produits intermédiaires représentés par la formule (II), la formule (III), la formule (IV) et la formule (V).
• Identification of sex pheromones from cowpea weevil,Callosobruchus maculatus, and related studies withC. analis (coleoptera: Bruchidae)
  作者：Thomas W. Phillips、Joel K. Phillips、Francis X. Webster、Rong Tang、Wendell E. Burkholder

  DOI：10.1007/bf02029543

  日期：1996.12

  Female cowpea weevils, Callosobruchus maculatus, produce a sex pheromone that elicits orientation and sexual behavior in males. Bioassay-directed isolation of the sex pheromone was conducted and compounds in the active fraction were identified and synthesized. Volatiles were collected from individual virgin females by adsorption on filter paper discs and hexane extraction. A bioassay was used in which the locomotory response of single males in glass vials was recorded upon exposure to treatments or controls. Crude extracts were subjected to silica gel column chromatography with solvents of increasing polarity; all activity eluted with methanol. Activity in the highly polar methanol fraction suggested a carboxylic acid or a compound with multiple polar functionality. Acid-base partitioning of the crude extract isolated all activity in the acid fraction, confirming that the pheromone was a carboxylic acid. The acid fraction was further fractionated by preparative GC with a Carbowax column. The most active GC fraction contained the following five 8-carbon acids identified by GC-MS and comparison with synthetic candidates: 3-methyleneheptanoic acid, (Z)-3-methyl-3-heptenoic acid, (E)-3-methyl-3-heptenoic acid, (Z)-3-methyl-2-heptenoic acid, and (E)-3-methyl-2-heptenoic acid. Each of the synthetic acids was active individually for males, and combinations of two or more of the acid pheromones had an additive effect. Upwind flight responses to natural and synthetic pheromones were observed in a flight tunnel. (Z)-3-Methyl-2-heptenoic acid was previously identified as the sex pheromone for the related C. analis, but this and the other four acid pheromones from C. maculatus were inactive for male C. analis. There was no cross-attraction between C. maculatus and C. analis in reciprocal studies using extracted volatiles from females of both species, GCMS analysis of C. analis female volatiles failed to detect any of the C. maculatus compounds but did find an unidentified C-8 acid with a GC retention time different from any of the C. maculatus pheromones.
• Photochemical reaction of trialkylboranes and β-dicarbonyl compounds
  作者：Kiitiro Utimoto、Toshio Tanaka、Hitosi Nozaki

  DOI：10.1016/s0040-4039(01)84536-6

  日期：1972.1