3,4-dichlorophenyl propanoate | 17847-52-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 3,4-dichlorophenyl propanoate
• 英文别名: 4-Propionyloxy-1,2-dichlor-benzol；(3,4-Dichlorophenyl) propanoate
• CAS: 17847-52-8
• 化学式: C₉H₈Cl₂O₂
• mdl: MFCD25977880
• 分子量: 219.067
• InChiKey: SRDCNPGSNBLMQK-UHFFFAOYSA-N

物化性质

• 沸点：
  290.0±30.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-dichlorophenyl propanoate 在 三氯化铝 作用下， 反应 3.0h， 生成 1-(4,5-dichloro-2-hydroxyphenyl)propan-1-one
  参考文献：
  名称：

  Rate of Enolate Formation Is Not Very Sensitive to the Hydrogen Bonding Ability of Donors to Carboxyl Oxygen Lone Pair Acceptors; A Ramification of the Principle of Non-Perfect Synchronization for General-Base-Catalyzed Enolate Formation

  摘要：

  Two series of structures (1 and 2) possessing intramolecular hydrogen bonds to the lone-pair electrons of carbonyl oxygens have been examined to reveal the influence of the pK(a) of the hydrogen-bond donor on the rate of general -base -catalyzed enolate formation. The geometry of the hydrogen bonds is well accepted to be appropriate for intramolecular hydrogen-bond formation. Yet, as revealed by Bronsted plots, both series show very little dependence of the rate of enolate formation on the hydrogen-bond donor ability. The intramolecular hydrogen bonds give rate enhancements only on the order of 10-100-fold, and corrected Bronsted alpha-values are slightly below 0.1. The results can be understood by interpreting them in light of the Principle of Non-Perfect Synchronization. The results are consistent with the proton transfer occurring through an asynchronous transition state with the developing negative charge localized on carbon. We postulate that catalysts of enolate formation will be most effective if the binding groups are focused on stabilizing negative charge that is forming on the enolate carbon rather than on the enolate oxygen.

  DOI：

  10.1021/ja0306011
• 作为产物：
  描述：

  3,4-二氯苯酚 、 丙酰氯 在 sodium hydroxide 作用下， 以 乙腈 为溶剂， 反应 17.25h， 生成 3,4-dichlorophenyl propanoate
  参考文献：
  名称：

  Rate of Enolate Formation Is Not Very Sensitive to the Hydrogen Bonding Ability of Donors to Carboxyl Oxygen Lone Pair Acceptors; A Ramification of the Principle of Non-Perfect Synchronization for General-Base-Catalyzed Enolate Formation

  摘要：

  Two series of structures (1 and 2) possessing intramolecular hydrogen bonds to the lone-pair electrons of carbonyl oxygens have been examined to reveal the influence of the pK(a) of the hydrogen-bond donor on the rate of general -base -catalyzed enolate formation. The geometry of the hydrogen bonds is well accepted to be appropriate for intramolecular hydrogen-bond formation. Yet, as revealed by Bronsted plots, both series show very little dependence of the rate of enolate formation on the hydrogen-bond donor ability. The intramolecular hydrogen bonds give rate enhancements only on the order of 10-100-fold, and corrected Bronsted alpha-values are slightly below 0.1. The results can be understood by interpreting them in light of the Principle of Non-Perfect Synchronization. The results are consistent with the proton transfer occurring through an asynchronous transition state with the developing negative charge localized on carbon. We postulate that catalysts of enolate formation will be most effective if the binding groups are focused on stabilizing negative charge that is forming on the enolate carbon rather than on the enolate oxygen.

  DOI：

  10.1021/ja0306011

文献信息

• [EN] PIPERAZINO DERIVATIVES AS NEUROKININ ANTAGONISTS<br/>[FR] DERIVES PIPERAZINO EN TANT QU'ANTAGONISTES DES NEUROKININES
  申请人：SCHERING CORPORATION

  公开号：WO1996034864A1

  公开（公告）日：1996-11-07

  (EN) The invention relates to compounds of formula (I). These compounds are neurokinin antagonists. These compounds are useful in the treatment of chronic airway diseases such as asthma.(FR) L'invention concerne des composés de la formule (I), qui sont des antagonistes des neurokinines et sont utiles dans le traitement de maladies chroniques des voies aériennes telles que l'asthme.

  该发明涉及公式（I）的化合物。这些化合物是神经肽拮抗剂。这些化合物在治疗慢性呼吸道疾病，如哮喘方面非常有用。
• PROCESS FOR PRODUCING THIOPHENE COMPOUND AND INTERMEDIATE THEREOF
  申请人：Yanagihara Kazufumi

  公开号：US20110124884A1

  公开（公告）日：2011-05-26

  To provide a novel process for producing a 2-aryl-3-hydroxy-4-substituted carbonyl thiophene compound or an intermediate thereof useful as an intermediate for production of medicines and agricultural chemicals. A 2-aryl acetate compound represented by the formula (1): wherein R 1 is an aryl group or the like, R 4 is a C 1-3 alkyl group or the like, and X is a leaving group, is reacted with a thioacetic acid compound to form a thioacetyl compound (3), the thioacetyl compound (3) is reacted with a vinyl ketone compound to form a γ-ketosulfide compound (5), which is cyclized under basic conditions to form a dihydrothiophene compound (6), and the dihydrothiophene compound (6) is oxidized by using an oxidizing agent to produce a 2-aryl-3-hydroxy-4-substituted carbonyl thiophene compound (7).

  提供一种新型方法，用于生产用作药物和农药中间体的2-芳基-3-羟基-4-取代羰基噻吩化合物或其中间体。将式（1）代表的2-芳基乙酸酯化合物：其中R1是芳基或类似物，R4是C1-3烷基或类似物，X是离去基团，与硫代乙酸化合物反应形成硫代乙酰化合物（3），硫代乙酰化合物（3）与乙烯基酮化合物反应形成γ-酮磺醚化合物（5），在碱性条件下环化形成二氢噻吩化合物（6），使用氧化剂氧化二氢噻吩化合物（6）以产生2-芳基-3-羟基-4-取代羰基噻吩化合物（7）。
• NOVEL CYSTEINE PROTEASE INHIBITORS AND THEIR THERAPEUTIC APPLICATIONS
  申请人：Guedat Philippe

  公开号：US20090215786A1

  公开（公告）日：2009-08-27

  The present invention concerns new compounds of formula (I), their process of preparation and their therapeutic use.

  本发明涉及一种新的化合物(I)的配方、制备方法及其治疗用途。
• PROCESS FOR PRODUCTION OF THIOPHENE COMPOUND AND INTERMEDIATE THEREOF
  申请人：Nissan Chemical Industries, Ltd.

  公开号：EP2246343A1

  公开（公告）日：2010-11-03

  To provide a novel process for producing a 2-aryl-3-hydroxy-4-substituted carbonyl thiophene compound or an intermediate thereof useful as an intermediate for production of medicines and agricultural chemicals. A 2-aryl acetate compound represented by the formula (1): wherein R1 is an aryl group or the like, R4 is a C1-3 alkyl group or the like, and X is a leaving group, is reacted with a thioacetic acid compound to form a thioacetyl compound (3), the thioacetyl compound (3) is reacted with a vinyl ketone compound to form a γ-ketosulfide compound (5), which is cyclized under basic conditions to form a dihydrothiophene compound (6), and the dihydrothiophene compound (6) is oxidized by using an oxidizing agent to produce a 2-aryl-3-hydroxy-4-substituted carbonyl thiophene compound (7).

  提供一种生产 2-芳基-3-羟基-4-取代羰基噻吩化合物或其中间体的新工艺，该化合物或其中间体可用作生产药物和农用化学品的中间体。 由式（1）代表的 2-芳基乙酸酯化合物： 其中 R1 是芳基或类似基团，R4 是 C1-3 烷基或类似基团，X 是离去基团，与硫代乙酸化合物反应生成硫代乙酰基化合物 (3)，硫代乙酰基化合物 (3) 与乙烯基酮化合物反应生成γ-酮硫化合物 (5)、在碱性条件下环化形成二氢噻吩化合物 (6)，使用氧化剂氧化二氢噻吩化合物 (6)，生成 2-芳基-3-羟基-4-取代羰基噻吩化合物 (7)。
• Pagani; Baruffini; Borgna, Farmaco, Edizione Scientifica, 1967, vol. 22, # 12, p. 1019 - 1036
  作者：Pagani、Baruffini、Borgna、Gialdi

  DOI：——

  日期：——