(R)-2-(2,4-dichlorophenyl)oxirane | 62566-67-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-(2,4-dichlorophenyl)oxirane
• 英文别名: (R)-o,p-dichlorostyrene oxide；(2R)-2-(2,4-Dichlorophenyl)oxirane
• CAS: 62566-67-0
• 化学式: C₈H₆Cl₂O
• 分子量: 189.041
• InChiKey: ZRMLHFOKDLDAIB-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-2-(2,4-dichlorophenyl)oxirane 在 potassium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 mineral oil 为溶剂， 反应 18.0h， 生成 (R)-1-[2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole
  参考文献：
  名称：

  Asymmetric Chemoenzymatic Synthesis of Miconazole and Econazole Enantiomers. The Importance of Chirality in Their Biological Evaluation

  摘要：

  A simple and novel chemoenzymatic route has been applied for the first time in the synthesis of miconazole and econazole single enantiomers. Lipases and oxidoreductases have been tested in stereoselective processes; the best results were attained with oxidoreductases for the introduction of chirality in an adequate intermediate. The behaviors of a series of ketones and racemic alcohols in bioreductions and acetylation procedures, respectively, have been investigated; the best results were found with alcohol dehydrogenases A and T, which allowed the production of (R)-2-chloro-1-(2,4-dichlorophenyl)ethanol in enantiopure form under very mild reaction conditions. Final chemical modifications have been performed in order to isolate the target fungicides miconazole and econazole both as racemates and as single enantiomers. Biological evaluation of the racemates and single enantiomers has shown remarkable differences against the growth of several microorganisms; while (R)-miconazole seemed to account for most of the biological activity of racemic miconazole on all the strains tested, both enantiomers of econazole showed considerable biological activities. In this manner, (R)-econazole showed higher values against Candida krusei, while higher values were observed for (S)-econazole against Cryptococcus neoformans, Penicillium chrysogenum, and Aspergillus niger.

  DOI：

  10.1021/jo102459w
• 作为产物：
  描述：

  2,2',4'-三氯苯乙酮 在 alcohol dehydrogenase PR₂ 、 水 、 异丙醇 、 还原型辅酶II(NADPH)四钠盐 、 sodium hydroxide 、 magnesium chloride 作用下， 以 乙醇 为溶剂， 反应 27.0h， 生成 (R)-2-(2,4-dichlorophenyl)oxirane
  参考文献：
  名称：

  Asymmetric Chemoenzymatic Synthesis of Miconazole and Econazole Enantiomers. The Importance of Chirality in Their Biological Evaluation

  摘要：

  A simple and novel chemoenzymatic route has been applied for the first time in the synthesis of miconazole and econazole single enantiomers. Lipases and oxidoreductases have been tested in stereoselective processes; the best results were attained with oxidoreductases for the introduction of chirality in an adequate intermediate. The behaviors of a series of ketones and racemic alcohols in bioreductions and acetylation procedures, respectively, have been investigated; the best results were found with alcohol dehydrogenases A and T, which allowed the production of (R)-2-chloro-1-(2,4-dichlorophenyl)ethanol in enantiopure form under very mild reaction conditions. Final chemical modifications have been performed in order to isolate the target fungicides miconazole and econazole both as racemates and as single enantiomers. Biological evaluation of the racemates and single enantiomers has shown remarkable differences against the growth of several microorganisms; while (R)-miconazole seemed to account for most of the biological activity of racemic miconazole on all the strains tested, both enantiomers of econazole showed considerable biological activities. In this manner, (R)-econazole showed higher values against Candida krusei, while higher values were observed for (S)-econazole against Cryptococcus neoformans, Penicillium chrysogenum, and Aspergillus niger.

  DOI：

  10.1021/jo102459w

文献信息

• Sulfonium ylide epoxidation reactions: methylene transfer
  作者：Benjamin R. Bellenie、Jonathan M. Goodman

  DOI：10.1039/b316653h

  日期：——

  Using a D-mannitol derived chiral sulfide, terminal epoxides are formed in up to 76% ee; the first example of double asymmetric induction in a sulfonium methylide epoxidation is reported and an improved method of generating sulfonium ylides is detailed.

  使用D-甘露糖醇衍生的手性硫化物，可以形成高达76％ee的末端环氧化物。报道了methyl甲基环氧化中双不对称诱导的第一个例子，并详细描述了产生酰的改进方法。
• Neurotherapeutic azole compounds
  申请人：Choi Moon Yong

  公开号：US20060258718A1

  公开（公告）日：2006-11-16

  Azole compounds containing carbamoyl group and pharmaceutically useful salts thereof are described. The compounds are effective anticonvulsants which are used in the treatment of disorders of the central nervous system, especially as anxiety, depression, convulsion, epilepsy, migraine, bipolar disorder, drug abuse, smoking, ADHD, obesity, sleep disorder, neuropathic pain, stroke, cognitive impairment, neurodegeneration, stroke and muscle spasm.

  本文介绍了含有氨基甲酰基的唑类化合物及其药用盐。这些化合物是有效的抗癫痫药物，可用于治疗中枢神经系统疾病，特别是焦虑、抑郁、惊厥、癫痫、偏头痛、双相障碍、药物滥用、吸烟、注意力缺陷多动障碍、肥胖症、睡眠障碍、神经痛、中风、认知障碍、神经退行性疾病、中风和肌肉痉挛。
• Production of optically active 2-halo-1-(substituted phenyl)-ethanol and substituted styrene oxide
  申请人：Nihon Nohyaku Co., Ltd.

  公开号：EP0763513A2

  公开（公告）日：1997-03-19

  A process for producing optically active 2-halo-1-(substituted phenyl)ethanol of a formula (Ia) or optically active styrene oxide of a formula (Ib). The process comprises the steps of reacting a compound of a formula (II) with phthalic anhydride to give a compound of a formula (III), performing optical resolution on the resulting compound using an optically active organic amine as a resolving agent, and finally performing hydrolysis or alcoholysis on the optically resolved compound (Ia) or (Ib). The scheme of the above process is: wherein X represents a halogen atom, Y represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkyl group or a C1-C6 haloalkoxy group, Z represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group, n is 0 or an integer of 1 to 3 and m is 0 or an integer of 1 to 2. The resulting optically active compounds are useful as an intermediate for medicines.

  一种生产光学活性 2-卤代-1-(取代苯基)乙醇式(Ia)或光学活性氧化苯乙烯式(Ib)的工艺。该工艺包括以下步骤：将式（II）化合物与邻苯二甲酸酐反应生成式（III）化合物，使用光学活性有机胺作为分解剂对生成的化合物进行光学分解，最后对光学分解后的化合物（Ia）或（Ib）进行水解或醇解。上述工艺的方案为 其中 X 代表卤素原子，Y 代表氢原子、卤素原子、C1-C6 烷基、C1-C6 烷氧基、C1-C6 卤代烷基或 C1-C6 卤代烷氧基，Z 代表氢原子、卤素原子或 C1-C6 烷基，n 为 0 或 1 至 3 的整数，m 为 0 或 1 至 2 的整数。
• A switch in enantiomer preference between mitochondrial F1F0-ATPase chemotypes
  作者：Sharon N. Bisaha、Mary F. Malley、Andrew Pudzianowski、Hossain Monshizadegan、Paulina Wang、Cort S. Madsen、Jack Z. Gougoutas、Philip D. Stein

  DOI：10.1016/j.bmcl.2005.03.115

  日期：2005.6

  The preferred absolute configuration of two series of F1F0-ATP synthase inhibitors was determined. Although the configuration of the active enantiomer in each series is different, each series presents the same 'triaryl' pharmacophore to the enzyme binding site. (c) 2005 Elsevier Ltd. All rights reserved.
• NEUROTHERAPEUTIC AZOLE COMPOUNDS
  申请人：SK Holdings Co., Ltd.

  公开号：EP1879873A1

  公开（公告）日：2008-01-23