phenylketene diethylacetal | 13049-42-8

• 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: phenylketene diethylacetal
• 英文别名: phenyl-ketene-diethylacetal；Phenyl-keten-diaethylacetal；β.β-Diaethoxy-styrol；Phenyl-keten-diethyl-acetal；Phenylketen-diaethyl-acetal；Phenylketen-diaethylacetal；(2,2-Diethoxyvinyl)benzene；2,2-diethoxyethenylbenzene
• CAS: 13049-42-8
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: MFJMVFHTVHWRCC-UHFFFAOYSA-N

物化性质

• 沸点：
  86-88 °C(Press: 0.2 Torr)
• 密度：
  1.005 g/cm3(Temp: 27 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  phenylketene diethylacetal 在 甲基磺酰胺 、 β-AD-Mix 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 水 、 sodium sulfite 作用下， 以 水 、 叔丁醇 为溶剂， 反应 0.75h， 以76%的产率得到D-(-)-扁桃酸乙酯
  参考文献：
  名称：

  Asymmetric Nucleophilic Acylation of Aldehydes via 1,1-Heterodisubstituted Alkenes

  摘要：

  Aldehydes are asymmetrically acylated by a two step sequence that is initiated by a homologation step to 1,1-heterodisubstituted alkenes followed by asymmetric dihydroxylation. Thus, ketene O,S-acetals are efficiently prepared from aldehydes by a Peterson olefination with lithiated methoxy-phenylthiotrimethylsilyl methane 14 as the C-1 source. Although they are dihydroxylated with the Sharpless catalyst with moderate to good enantioselectivity (62-80% ee), the process is not efficient owing to the low chemical yields of the desired alpha-hydroxy methyl esters (7-37%). Use of the corresponding sulfoxide 24 or sulfon 25 led to an improved chemical yield of alpha-hydroxy methyl ester 19, but the stereoselectivity was diminished. In contrast, intermediate ketene O,O-acetals are prepared by a Horner-Wittig reaction with phosphine oxide 31 and are dihydroxylated both with good chemical and stereochemical yield. The concept is applicable to aromatic, aliphatic, and chiral aldehydes. For example, this short sequence allows exclusive and independent preparation of both diastereomeric heptoses 69a and 69b.

  DOI：

  10.1002/(sici)1521-3765(19990802)5:8<2270::aid-chem2270>3.0.co;2-l
• 作为产物：
  描述：

  苯甲醛 在 potassium tert-butylate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.08h， 生成 phenylketene diethylacetal
  参考文献：
  名称：

  用于合成烯酮，O，O-乙缩醛的Horner-Wittig解决方案。

  摘要：

  醛和酮可以通过与二烷氧基甲基二苯基膦氧化物的霍纳-威蒂希反应转化为它们的同源烯酮OO-乙缩醛。

  DOI：

  10.1016/s0040-4039(00)81641-x

文献信息

• Amine-based and amide-based inhibitors of semicarbazide-sensitive amine oxidase (SSAO) enzyne activity and VAP-1 mediated adhesion useful for treatment of diseases
  申请人：Salter-Cid M. Luisa

  公开号：US20060025438A1

  公开（公告）日：2006-02-02

  Compositions and methods are disclosed for inhibiting semicarbazide-sensitive amine oxidase (SSAO), also known as vascular adhesion protein-1 (VAP-1). The compounds disclosed are amine-containing and amide-containing compounds. The compounds and compositions are useful for treatment of diseases, including inflammation, inflammatory diseases and autoimmune disorders.

  本发明揭示了一种抑制半卡巴肼敏感性胺基氧化酶（SSAO）的化合物和方法，SSAO也被称为血管黏附蛋白-1（VAP-1）。所揭示的化合物为含有胺基和酰胺基的化合物。这些化合物和组合物对于治疗炎症、炎症性疾病和自身免疫性疾病等疾病是有用的。
• Amine-based and amide-based inhibitors of semicarbazide-sensitive amine oxidase (SSAO)enzyme activity and VAP-1 mediated adhesion useful for treatment of diseases
  申请人：Salter-Cid M. Luisa

  公开号：US20070078157A1

  公开（公告）日：2007-04-05

  Compositions and methods are disclosed for inhibiting semicarbazide-sensitive amine oxidase (SSAO), also known as vascular adhesion protein-1 (VAP-1). The compounds disclosed are amine-containing and amide-containing compounds. The compounds and compositions are useful for treatment of diseases, including inflammation, inflammatory diseases and autoimmune disorders.

  本发明公开了抑制半卡巴肼敏感性胺氧化酶（SSAO），也称为血管黏附蛋白-1（VAP-1）的组合物和方法。所公开的化合物是含有胺基和酰胺基的化合物。这些化合物和组合物可用于治疗炎症、炎症性疾病和自身免疫性疾病等疾病。
• AMINE-BASED AND AMIDE-BASED INHIBITORS OF SEMICARBAZIDE-SENSITIVE AMINE OXIDASE (SSAO) ENZYME ACTIVITY AND VAP-1 MEDIATED ADHESION USEFUL FOR TREATMENT OF DISEASES
  申请人：SALTER-CID LUISA M.

  公开号：US20120172392A1

  公开（公告）日：2012-07-05

  Compositions and methods are disclosed for inhibiting semicarbazide-sensitive amine oxidase (SSAO), also known as vascular adhesion protein-1 (VAP-1). The compounds disclosed are amine-containing and amide-containing compounds. The compounds and compositions are useful for treatment of diseases, including inflammation, inflammatory diseases and autoimmune disorders.

  本文揭示了一种抑制半卡巴肼敏感性胺氧化酶（SSAO），也称为血管粘附蛋白-1（VAP-1）的组合物和方法。所揭示的化合物包括含胺和含酰胺的化合物。这些化合物和组合物对于治疗疾病，包括炎症、炎症性疾病和自身免疫性疾病非常有用。
• Electrorheological fluids
  申请人：NIPPON SHOKUBAI KAGAKU KOGYO CO. LTD.

  公开号：EP0523300A1

  公开（公告）日：1993-01-20

  An electrorheological fluid composition comprising a dispersion of disperse-phase particles formed of a sulfonated polymer possessing aromatic rings substituted with sulfonic acid groups in an electrically non-conducting oil which electrorheological fluid is characterized by the fact that the number of sulfonic acid groups in said sulfonated polymer forming said disperse-phase particles exceeds the number of aromatic rings present in said sulfonated polymer.

  一种电流变液组合物，包含由磺化聚合物形成的分散相颗粒的分散体，该磺化聚合物具有被磺酸基团取代的芳香环，分散在不导电的油中，该电流变液的特点是形成所述分散相颗粒的所述磺化聚合物中磺酸基团的数量超过所述磺化聚合物中芳香环的数量。
• Amines and amides for the treatment of diseases
  申请人：LA JOLLA PHARMACEUTICAL CO.

  公开号：EP2283833A2

  公开（公告）日：2011-02-16

  Compositions and methods are disclosed for inhibiting semicarbazide-sensitive amine oxidase (SSAO), also known as vascular adhesion protein-1 (VAP-1). The compounds disclosed are amine-containing and amide-containing compounds. The compounds and compositions are useful for treatment of diseases, including inflammation, inflammatory diseases and autoimmune disorders.

  本发明公开了用于抑制半卡巴肼敏感胺氧化酶（SSAO）（又称血管粘附蛋白-1（VAP-1））的化合物和方法。所公开的化合物是含胺和含酰胺的化合物。这些化合物和组合物可用于治疗疾病，包括炎症、炎性疾病和自身免疫性疾病。