1-[5-(2-氯苯基)-2-呋喃基]乙酮 | 675596-28-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-[5-(2-氯苯基)-2-呋喃基]乙酮
• 英文名称: 1-(5-(2-chlorophenyl)furan-2-yl)ethanone
• 英文别名: 1-[5-(2-Chlorophenyl)-2-furyl]ethanone；1-[5-(2-chlorophenyl)furan-2-yl]ethanone
• CAS: 675596-28-8
• 化学式: C₁₂H₉ClO₂
• 分子量: 220.655
• InChiKey: OQKZBDRVDZZGAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  1-[5-(2-氯苯基)-2-呋喃基]乙酮 在 吡啶 、 Burkholderia cepacia lipase 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 pyridinium hydrobromide perbromide 、 18-冠醚-6 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 16.5h， 生成 1-(5-(2-chlorophenyl)furan-2-yl)-2-hydroxyethyl acetate
  参考文献：
  名称：

  Sequential use of regio- and stereoselective lipases for the efficient kinetic resolution of racemic 1-(5-phenylfuran-2-yl)ethane-1,2-diols

  摘要：

  Possible routes for the enzymatic transformation of various substituted 1-(5-phenylfuran-2-yl)ethane-1,2-diols and their mono- and diacetylated counterparts were studied. Combining the regioselectivity of LPS mediated acylation of the starting racemic diols, the stereoselectivity of LAK shown in the enantiomer selective transformation of the previously formed racemic primary acetates and the LPS mediated mild hydrolysis-alcoholysis of the resolution products, an efficient preparative scale procedure for the synthesis of various highly enantiomerically enriched (R)- and (S)-phenylfuran-2-yl-ethane-1,2-diols has been developed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.03.006
• 作为产物：
  描述：

  2-乙酰基呋喃 、 2-chlorobenzenediazonium chloride 在 copper dichloride 作用下， 以 水 为溶剂， 反应 24.0h， 以45%的产率得到1-[5-(2-氯苯基)-2-呋喃基]乙酮
  参考文献：
  名称：

  Substituent effects on the stereochemical outcome of the baker’s yeast-mediated biotransformation of α-hydroxy- and α-acetoxymethyl-5-phenylfuran-2-yl-ethanones

  摘要：

  In this Letter the baker's yeast-mediated biotransformation of variously substituted alpha-hydroxy- and alpha-acetoxymethyl-5-phenylfuran-2-yl-ethanones is described. The stereochemical outcome of the reactions was strongly influenced by the nature of the substituents on the phenyl ring. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.004

文献信息

• Chemoenzymatic Preparation of 1-Heteroarylethanamines of Low Solubility
  作者：Jürgen Brem、László-Csaba Bencze、Arto Liljeblad、Mihaela C. Turcu、Csaba Paizs、Florin-Dan Irimie、Liisa T. Kanerva

  DOI：10.1002/ejoc.201200330

  日期：2012.6

  benzothiophen-, and phenylfuran-based 1-heteroarylethanamines were prepared at close to theoretical yields by using Candida antarctica lipase B (Novozym 435) catalyzed (R)-selective N-acylation with isopropyl butanoate (enantiomeric ratio E > 200). The use of N-methyl-2-pyrrolidinone (NMP) as a cosolvent (1:30) in isopropyl butanoate solved the problem of low solubility of the compounds. Instability of

  通过使用南极念珠菌脂肪酶 B (Novozym 435) 催化 (R) 选择性 N-酰化与丁酸异丙酯 (对映体比率 E > 200）。使用 N-甲基-2-吡咯烷酮 (NMP) 作为共溶剂 (1:30) 在丁酸异丙酯中解决了化合物溶解度低的问题。通过使用南极念珠菌脂肪酶 A 作为商业 CAL-A-CLEA 制剂用于在水中脱保护 N-酰化 (R) 对映异构体，解决了杂环系统对传统酸和碱催化水解的不稳定性。在 Novozym 435 存在下，也观察到外消旋丁酰胺的缓慢、高度对映选择性 (E > 200) 水解。
• Stereoselective bioreduction of 1-(5-phenylfuran-2-yl)-ethanones mediated by baker's yeast
  作者：Maria Trif、Noémi Hajnalka Kalló、Mara Ana Naghi、László Csaba Bencze

  DOI：10.3109/10242422.2011.638374

  日期：2012.3

  Abstract Baker's yeast mediated reduction of various phenylfuran-2-yl-ethanones has been studied. The influence of the reaction conditions, the type and position of the substituents, as well the presence of various additives on the enantiomeric composition of the products and the reaction yield are discussed. The absolute configuration of the reaction products was established using a retrosynthetic

  摘要 已经研究了贝克酵母介导的各种苯基呋喃-2-基-乙酮的还原。讨论了反应条件、取代基的类型和位置以及各种添加剂的存在对产物对映体组成和反应产率的影响。使用逆合成程序建立反应产物的绝对构型。
• Aryl-link-aryl substituted thiazolidine-dione and oxazolidine-dione as sodium channel blockers
  申请人：Ayer B. Michelle

  公开号：US20050165072A1

  公开（公告）日：2005-07-28

  Aryl-link-aryl thiazolidine-dione and aryl-link-aryl oxazolidine-dione compounds are sodium channel blockers; pharmaceutical compositions that include an effective amount of the aryl-link-aryl thiazolidine-dione and aryl-link-aryl oxazolidine-dione compounds and a pharmaceutically acceptable carrier, and a method of treatment of acute pain, chronic pain, visceral pain, inflammatory pain, or neuropathic pain, as well as initable bowel syndrome, Cnohns disease, epilepsy, partial and generalized tonic seizures, multiple sclerosis, bipolar depression, and tachy-arrhythmias by the administration of an effective amount of aryl-link-aryl thiazolidine-dione and aryl-link-aryl oxazolidine-dione compounds are described.

  Aryl-link-aryl噻唑烷二酮和aryl-link-aryl噁唑烷二酮化合物是钠通道阻滞剂；其中包括有效量的aryl-link-aryl噻唑烷二酮和aryl-link-aryl噁唑烷二酮化合物以及药学上可接受的载体的制药组合物，以及通过给予有效量的aryl-link-aryl噻唑烷二酮和aryl-link-aryl噁唑烷二酮化合物的方法治疗急性疼痛、慢性疼痛、内脏疼痛、炎症性疼痛或神经病性疼痛，以及易激性肠综合症、克罗恩病、癫痫、部分和全身强直性发作、多发性硬化、双相抑郁症和快速心律失常。
• EP1501509A4
  申请人：——

  公开号：EP1501509A4

  公开（公告）日：2009-07-15
• ARYL-LINK-ARYL SUBSTITUTED THIAZOLIDINE-DIONE AND OXAZOLIDINE-DIONE AS SODIUM CHANNEL BLOCKERS
  申请人：Merck & Co., Inc.

  公开号：EP1501509A2

  公开（公告）日：2005-02-02