6-phenoxyhexanal | 19790-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-phenoxyhexanal
• CAS: 19790-63-7
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: GRIZYJVXLJZHDV-UHFFFAOYSA-N

物化性质

• 沸点：
  306.2±25.0 °C(Predicted)
• 密度：
  0.994±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  1-脱氧野尻霉素 、 6-phenoxyhexanal 在 溶剂黄146 、 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 25.0h， 以89%的产率得到(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(6-phenoxyhexyl)piperidine-3,4,5-triol
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of N-Alkylated Deoxynojirimycin (DNJ) Derivatives for the Treatment of Dengue Virus Infection

  摘要：

  We recently described the discovery of oxygenated N-alkyl deoxynojirimycin (DNJ) derivative 7 (CM-10-18) with antiviral activity against dengue virus (DENY) infection both in vitro and in vivo. This imino sugar was promising but had an EC50 against DENY in BHK cells of 6.5 mu M, which limited its use in in vivo. Compound 7 presented structural opportunities for activity relationship analysis, which we exploited and report here. These structure activity relationship studies led to analogues 2h, 2l, 3j, 3l, 3v, and 4b-4c with nanomolar antiviral activity (EC50 = 0.3-0.5 mu M) against DENY infection, while maintaining low cytotoxicity (CC50 > 500 mu M, SI > 1000). In male Sprague-Dawley rats, compound 3l was well tolerated at a dose up to 200 mg/kg and displayed desirable PK profiles, with significantly improved bioavailability (F = 92 +/- 4%).

  DOI：

  10.1021/jm300171v
• 作为产物：
  描述：

  6-溴正己醇 在 silica gel 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 6-phenoxyhexanal
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of N-Alkylated Deoxynojirimycin (DNJ) Derivatives for the Treatment of Dengue Virus Infection

  摘要：

  We recently described the discovery of oxygenated N-alkyl deoxynojirimycin (DNJ) derivative 7 (CM-10-18) with antiviral activity against dengue virus (DENY) infection both in vitro and in vivo. This imino sugar was promising but had an EC50 against DENY in BHK cells of 6.5 mu M, which limited its use in in vivo. Compound 7 presented structural opportunities for activity relationship analysis, which we exploited and report here. These structure activity relationship studies led to analogues 2h, 2l, 3j, 3l, 3v, and 4b-4c with nanomolar antiviral activity (EC50 = 0.3-0.5 mu M) against DENY infection, while maintaining low cytotoxicity (CC50 > 500 mu M, SI > 1000). In male Sprague-Dawley rats, compound 3l was well tolerated at a dose up to 200 mg/kg and displayed desirable PK profiles, with significantly improved bioavailability (F = 92 +/- 4%).

  DOI：

  10.1021/jm300171v

文献信息

• [EN] CARBOSTYRIL COMPOUND<br/>[FR] DÉRIVÉ DE CARBOSTYRILE
  申请人：OTSUKA PHARMA CO LTD

  公开号：WO2006035954A1

  公开（公告）日：2006-04-06

  The present invention provides a carbostyril compound represented by General Formula (1) or a salt thereof, wherein A is a direct bond, a lower alkylene group, or a lower alkylidene group; X is an oxygen atom or a sulfur atom; R4 and R5 each represent a hydrogen atom; the bond between the 3 and 4 positions of the carbostyril skeleton is a single bond or a double bond; R1 is a hydrogen atom, etc; R2 is a hydrogen atom, etc; and R3 is a hydrogen atom, etc. The carbostyril compound or salt thereof of the present invention induces the production of TFF, and thus is usable for the treatment and/or prevention of disorders such as alimentary tract diseases, oral diseases, upper respiratory tract diseases, respiratory tract diseases, eye diseases, cancers, and wounds.

  本发明提供了一种由通式（1）表示的羧基吲哚化合物或其盐，其中A是直链键、较低的烷基烯基或较低的烷基亚烯基；X是氧原子或硫原子；R4和R5分别表示氢原子；羧基吲哚骨架的3和4位置之间的键是单键或双键；R1是氢原子，等等；R2是氢原子，等等；R3是氢原子，等等。本发明的羧基吲哚化合物或其盐诱导TFF的产生，因此可用于治疗和/或预防消化道疾病、口腔疾病、上呼吸道疾病、呼吸道疾病、眼部疾病、癌症和伤口等疾病。
• DIARYLETHER DERIVATIVES AS ANTITUMOR AGENTS
  申请人：Matsuyama Hironori

  公开号：US20100004438A1

  公开（公告）日：2010-01-07

  An object of the present invention is to provide a medicinal drug much improved in anti tumor activity and excellent in safety. According to the present invention, there is provided a medicinal drug containing a compound represented by the following general formula (1) or a salt thereof as an active ingredient: [Formula 1] wherein X 1 represents a nitrogen atom or a group —CH═, R 1 represents a group -Z-R 6 , in which Z represents a group —CO—, a group —CH(OH)— or the like, R 6 represents a 5- to 15-membered monocyclic, dicyclic or tricyclic saturated or unsaturated heterocyclic group having 1 to 4 nitrogen atoms, oxygen atoms or sulfur atoms, R 2 represents a hydrogen atom or a halogen atom, Y represents a group —O—, a group —CO—, a group —CH(OH)— or a lower alkylene group, and A represents [Formula 2] wherein R 3 represents a hydrogen atom, a lower alkoxy group or the like, p represents 1 or 2, R 4 represents an imidazolyl lower alkyl group or the like.

  本发明的一个目的是提供一种在抗肿瘤活性方面大大改进且安全性优异的药物。根据本发明，提供了一种包含以下一般式（1）所表示的化合物或其盐作为活性成分的药物：[式1]其中X1代表氮原子或基团—CH═，R1代表一个基团-Z-R6，其中Z代表基团—CO—，基团—CH(OH)—或类似的基团，R6代表一个含有1至4个氮原子、氧原子或硫原子的5至15个成员的单环、双环或三环饱和或不饱和杂环基团，R2代表氢原子或卤原子，Y代表基团—O—，基团—CO—，基团—CH(OH)—或低碳烷基基团，A代表[式2]其中R3代表氢原子、低碳氧基基团或类似基团，p代表1或2，R4代表咪唑基低碳基团或类似基团。
• Regioselectivity of olefin oxidation by iodosobenzene catalyzed by metalloporphyrins : control by the catalyst
  作者：Daniel Mansuy、Jacques Leclaire、Marc Fontecave、Patrick Dansette

  DOI：10.1016/s0040-4020(01)91293-1

  日期：1984.1

  importance of these reactions greatly depends upon both the metal and porphyrin constituents of the catalyst. More particularly, the competition between epoxidation and allylic hydroxylation can be efficiently controlled by non-bonded interactions between the olefin and porphyrin substituents. No hydroxylation of the aromatic rings and no oxidative dealkylation of the ether function was detected.

  研究了在各种Fe-，Mn-或Cr-四芳基-卟啉存在下，碘代苯对三种单取代烯烃（6-苯氧基己-1-烯，己-1-烯和苯乙烯）氧化的区域选择性。已经发现，除了环氧化物以外，还从这种体系中形成了已知的产物，烯丙基醇和醛，后者不是由相应的环氧化物衍生而来的。这些反应的相对重要性在很大程度上取决于催化剂的金属和卟啉成分。更特别地，环氧化和烯丙基羟基化之间的竞争可以通过烯烃和卟啉取代基之间的非键相互作用来有效地控制。没有检测到芳环的羟基化，也没有检测到醚官能团的氧化脱烷基。
• Cr(salen)-catalyzed Asymmetric Addition of Allylstannane to Aldehydes
  作者：Yuya Shimada、Tsutomu Katsuki

  DOI：10.1246/cl.2005.786

  日期：2005.6

  Cr(salen) complex 3 was found to be an efficient catalyst for asymmetric addition of allyltributylstannane to non-branched aliphatic aldehydes, giving the corresponding homoallylic alcohols in a hi...

  发现 Cr(salen) 配合物 3 是烯丙基三丁基锡烷与非支化脂肪醛不对称加成的有效催化剂，在高...
• Highly Enantioselective Cr(salen)-Catalyzed Mukaiyama Aldol Reaction: Construction of δ-Hydroxy-β-keto Ester Derivatives
  作者：Tsutomu Katsuki、Yuya Shimada、Yuko Matsuoka、Ryo Irie

  DOI：10.1055/s-2003-43351

  日期：——

  Mukaiyama aldol reactions of silyl dienol ether and aldehydes proceeded with high enantioselectivity to give δ-hydroxy-β-keto ester derivatives by using chiral cationic Cr(salen) complex as catalyst in the presence of isopropyl alcohol and base (triethylamine or 2,6-dimethylpyridine).

  在异丙醇和碱（三乙胺或 2,6-二甲基吡啶）。