ethyl 4-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-3-cyclohexenecarboxylate | 444108-39-8

• 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: ethyl 4-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-3-cyclohexenecarboxylate
• 英文别名: 4-(2,3-dihydro-8-methoxy-1,4-benzodioxine-5-yl)-3-cyclohexenecarboxylic acid ethyl ester；4-(2,3-Dihydro-8methoxy-1,4-benzodioxine-5-yl)-3-cyclohexenecarboxylic acid ethyl ester；ethyl 4-(5-methoxy-2,3-dihydro-1,4-benzodioxin-8-yl)cyclohex-3-ene-1-carboxylate
• CAS: 444108-39-8
• 化学式: C₁₈H₂₂O₅
• 分子量: 318.37
• InChiKey: QGRUHTFIPXUVNA-UHFFFAOYSA-N

物化性质

• 熔点：
  88 °C
• 沸点：
  433.5±45.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-3-cyclohexenecarboxylate 在 三氟甲磺酸 、 potassium hydroxide 作用下， 以 乙醇 、 2,3,4-三氟甲苯 为溶剂， 反应 5.0h， 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-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-1-buten-3-ol 以71.8的产率得到ethyl 4-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-3-cyclohexenecarboxylate
  参考文献：
  名称：

  Org. Process Res. Dev. 2010, 14, 1182-1187

  摘要：

  DOI：

文献信息

• Brønsted Acid-Promoted Hydrocyanation of Arylalkenes
  作者：Arata Yanagisawa、Tetsuya Nezu、Shin-ichiro Mohri

  DOI：10.1021/ol902244e

  日期：2009.11.19

  Nonactivated arylalkenes are effectively converted to tertiary benzylic nitriles in the presence of triflic acid and trimethylsilyl cyanide. The hydrocyanation reactions result in good to excellent yield when electron-donating groups are substituted on the benzene ring. The reaction conditions are mild and relatively safe, notably without need for handling hazardous hydrogen cyanide gas, providing

  在三氟甲磺酸和三甲基甲硅烷基氰化物的存在下，未活化的芳基烯烃可以有效地转化为叔苄基腈。当给电子基团被取代在苯环上时，氢氰化反应导致良好或极好的收率。反应条件温和且相对安全，特别是无需处理危险的氰化氢气体，从而可轻松轻松地获得叔苄基腈。该反应被用于制备PDE4抑制剂（3）以及一系列类似物。
• 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：——
• 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.