1-[(3Z)-3-(chloromethylene)-2,3-dihydro-1-benzoxepin-7-yl]ethanone | 369376-61-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: 1-[(3Z)-3-(chloromethylene)-2,3-dihydro-1-benzoxepin-7-yl]ethanone
• 英文别名: (Z)-1-(3-chloromethylene-2,3-dihydrobenzo[b]oxepin-7-yl)ethanone；Pterulone；1-[(3Z)-3-(chloromethylidene)-1-benzoxepin-7-yl]ethanone
• CAS: 369376-61-4
• 化学式: C₁₃H₁₁ClO₂
• 分子量: 234.682
• InChiKey: QEWSARCWWQPUSM-YFHOEESVSA-N

物化性质

• 沸点：
  408.4±45.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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-[(3Z)-3-(chloromethylene)-2,3-dihydro-1-benzoxepin-7-yl]ethanone 在 碘 作用下， 以 四氯化碳 为溶剂， 反应 5.0h， 生成 1-[(3E)-3-(chloromethylene)-2,3-dihydro-1-benzoxepin-7-yl]ethanone
  参考文献：
  名称：

  Synthesis of the antifungal 1-benzoxepin pterulone

  摘要：

  The chlorinated 1-benzoxepin derivative pterulone (1a), a potent antifungal metabolite isolated from a Pterula species, was synthesised from 4,5-dihydro-2H-benzoxepin-3-one 6 by the oxidation of 6 to 3(2H)-oxepinone 7, a Wittig reaction that transformed the keto functionality of 7 to a chlorovinyl group, and a Friedel Craft's acetylation. The mixture of E and Z isomers (1a and 1b) obtained could transformed to pure pterulone (1a) by photochemical isomerisation and separation by chromatography. The yield was 23% starting from 6. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00640-8
• 作为产物：
  描述：

  benzo[b]oxepin-3(2H)-one 在 potassium tert-butylate 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 为溶剂， 反应 2.34h， 生成 1-[(3Z)-3-(chloromethylene)-2,3-dihydro-1-benzoxepin-7-yl]ethanone
  参考文献：
  名称：

  Synthesis of the antifungal 1-benzoxepin pterulone

  摘要：

  The chlorinated 1-benzoxepin derivative pterulone (1a), a potent antifungal metabolite isolated from a Pterula species, was synthesised from 4,5-dihydro-2H-benzoxepin-3-one 6 by the oxidation of 6 to 3(2H)-oxepinone 7, a Wittig reaction that transformed the keto functionality of 7 to a chlorovinyl group, and a Friedel Craft's acetylation. The mixture of E and Z isomers (1a and 1b) obtained could transformed to pure pterulone (1a) by photochemical isomerisation and separation by chromatography. The yield was 23% starting from 6. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00640-8

文献信息

• Efficient syntheses of pterulone, pterulone B and related analogues
  作者：Philippe Lemaire、Geneviève Balme、Philippe Desbordes、Jean-Pierre Vors

  DOI：10.1039/b306356a

  日期：——

  An efficient synthesis of the three halogenated naturally occurring products, pterulone (2), pterulone B (3) and alcohol 5, and of a wide range of related unnatural analogues has been achieved starting from the two readily available 1-benzoxepine sulfonyl-containing intermediates 6a and 6b. The biological activities of pterulone and some of the synthesized analogues were tested against a wide spectrum of phytopathogenic fungi.

  从两种容易获得的含 1-苯并氧杂环庚烷磺酰基的中间体 6a 和 6b 开始，高效合成了三种卤代天然产物蝶酮 (2)、蝶酮 B (3) 和醇 5 以及多种相关的非天然类似物。测试了紫檀酮和一些合成类似物对多种植物病原真菌的生物活性。
• Fungicidal 1-benzoxepin derivatives
  申请人：——

  公开号：US20040249173A1

  公开（公告）日：2004-12-09

  The invention concerns novel 1-benzoxepin derivatives, methods for preparing them, their use as fungicides, in particular in the form of fungicidal compositions, as well as methods for controlling phytopathogenic fungi of crops using said compounds or said compositions.

  这项发明涉及新颖的1-苯并噁二氧杂环庚烷衍生物，制备它们的方法，它们作为杀真菌剂的用途，特别是以杀真菌组合物的形式，以及利用这些化合物或组合物控制作物的植物病原真菌的方法。
• Total Synthesis and Bioactivity of Some Naturally Occurring Pterulones
  作者：Bas W. T. Gruijters、Albertus van Veldhuizen、Carel A. G. M. Weijers、Joannes B. P. A. Wijnberg

  DOI：10.1021/np010510m

  日期：2002.4.1

  The naturally occurring pterulones 1, 3, and 13 were synthesized in high overall yield from readily available methyl 3-(2-propenyl)-4-(2-propenyloxy)benzoate (6) by employing ring-closing metathesis (RCM) as a key step. The biological activities of the synthesized pterulones were tested using cells of Rhodotorulaglutinis and Saccharomyces cerevisiae.

  天然存在的信息素1、3和13通过使用闭环易位（RCM）作为易位化合物，由易于获得的3-（2-丙烯基）-4-（2-丙烯氧基）苯甲酸甲酯（6）合成。关键步骤。使用红假单胞菌和酿酒酵母的细胞测试了合成的蝶ter的生物活性。
• DERIVES DE 1-BENZOXEPINE FONGICIDES
  申请人：Bayer CropScience S.A.

  公开号：EP1417197A1

  公开（公告）日：2004-05-12
• US7071340B2
  申请人：——

  公开号：US7071340B2

  公开（公告）日：2006-07-04