3-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-1-buten-3-ol | 444108-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 3-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-1-buten-3-ol
• 英文别名: 3-(2,3-dihydro-8-methoxy-1,4-benzodioxine-5-yl)-1-butene-3-ol；2-(5-methoxy-2,3-dihydro-1,4-benzodioxin-8-yl)but-3-en-2-ol
• CAS: 444108-41-2
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: GGZLWPSUSBKBAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-1-buten-3-ol 在 三氟甲磺酸 、 4-甲基苯磺酸吡啶 、 potassium hydroxide 作用下， 以 乙醇 、 乙酸丙酯 、 2,3,4-三氟甲苯 为溶剂， 反应 13.0h， 生成 cis-4-cyano-4-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)cyclohexanecarboxylic acid
  参考文献：
  名称：

  A Practical Synthesis of the PDE4 Inhibitor, KW-4490

  摘要：

  A practical and scalable synthesis of a PDE4 inhibitor KW-4490 (1) was developed. This improved synthesis features the construction of the 1-arylcyclohexene (9) by the Diels-Alder reaction followed by a newly established Bronsted acid-promoted hydrocyanation. Subsequent crystallization-induced dynamic resolution enabled the high-yield production of the desired cis-isomer (cis-8). The synthesis was achieved in seven steps in 37% overall yield.

  DOI：

  10.1021/op1001287
• 作为产物：
  描述：

  3-甲氧基儿茶酚 在 aluminum (III) chloride 、 potassium carbonate 作用下， 以 四氢呋喃 、 硝基甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.92h， 生成 3-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-1-buten-3-ol
  参考文献：
  名称：

  A Practical Synthesis of the PDE4 Inhibitor, KW-4490

  摘要：

  A practical and scalable synthesis of a PDE4 inhibitor KW-4490 (1) was developed. This improved synthesis features the construction of the 1-arylcyclohexene (9) by the Diels-Alder reaction followed by a newly established Bronsted acid-promoted hydrocyanation. Subsequent crystallization-induced dynamic resolution enabled the high-yield production of the desired cis-isomer (cis-8). The synthesis was achieved in seven steps in 37% overall yield.

  DOI：

  10.1021/op1001287

文献信息

• Styrene derivatives and process for production thereof
  申请人：——

  公开号：US20040054197A1

  公开（公告）日：2004-03-18

  The present invention provides a compound represented by general formula (I): 1 [wherein m represents an integer of 0 to 4; R 1 , R 2 , R 3 and R 4 may be the same or different and each represents a hydrogen atom, substituted or unsubstituted lower alkyl, or the like; R 5 represents hydroxy, or substituted or unsubstituted lower alkoxy; R 6 represents a hydrogen atom or halogen; R 7 represents hydroxy, formyl, substituted or unsubstituted lower alkoxy, or the like; and R 8 represents a hydrogen atom, substituted or unsubstituted lower alkoxy, or the like], or a salt thereof.

  本发明提供了一种由通式(I)表示的化合物：1［其中，m表示0至4的整数；R1、R2、R3和R4可以相同也可以不同，每个代表氢原子、取代或未取代的低级烷基或类似物；R5代表羟基、取代或未取代的低级烷氧基；R6代表氢原子或卤素；R7代表羟基、甲酰基、取代或未取代的低级烷氧基或类似物；R8代表氢原子、取代或未取代的低级烷氧基或类似物］，或其盐。
• STYRENE DERIVATIVES AND PROCESS FOR PRODUCTION THEREOF
  申请人：Kyowa Hakko Kogyo Co., Ltd

  公开号：EP1362853A1

  公开（公告）日：2003-11-19

  The present invention provides a compound represented by general formula (I): [wherein m represents an integer of 0 to 4; R1, R2, R3 and R4 may be the same or different and each represents a hydrogen atom, substituted or unsubstituted lower alkyl, or the like; R5 represents hydroxy, or substituted or unsubstituted lower alkoxy; R6 represents a hydrogen atom or halogen; R7 represents hydroxy, formyl, substituted or unsubstituted lower alkoxy, or the like; and R8 represents a hydrogen atom, substituted or unsubstituted lower alkoxy, or the like], or a salt thereof.

  本发明提供了通式(I)代表的化合物： [其中 m 代表 0 至 4 的整数；R1、R2、R3 和 R4 可以相同或不同，各自代表氢原子、取代或未取代的低级烷基或类似物；R5 代表羟基、取代或未取代的低级烷氧基；R6 代表氢原子或卤素；R7 代表羟基、甲酰基、取代或未取代的低级烷氧基或类似物；以及 R8 代表氢原子、取代或未取代的低级烷氧基或类似物]，或其盐。
• EP1362853
  申请人：——

  公开号：——

  公开（公告）日：——
• Org. Process Res. Dev. 2010, 14, 1182-1187
  作者：

  DOI：——

  日期：——
• A Practical Synthesis of the PDE4 Inhibitor, KW-4490
  作者：Arata Yanagisawa、Koichiro Nishimura、Kyoji Ando、Tetsuya Nezu、Ayako Maki、Sachiko Kato、Wakako Tamaki、Eiichiro Imai、Shin-ichiro Mohri

  DOI：10.1021/op1001287

  日期：2010.9.17

  A practical and scalable synthesis of a PDE4 inhibitor KW-4490 (1) was developed. This improved synthesis features the construction of the 1-arylcyclohexene (9) by the Diels-Alder reaction followed by a newly established Bronsted acid-promoted hydrocyanation. Subsequent crystallization-induced dynamic resolution enabled the high-yield production of the desired cis-isomer (cis-8). The synthesis was achieved in seven steps in 37% overall yield.