2-chloro-6-cyano-6-(3-cyclopentyloxy-4-methoxyphenyl)-1-oxospiro[2.5]octane-2-carboxylic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-chloro-6-cyano-6-(3-cyclopentyloxy-4-methoxyphenyl)-1-oxospiro[2.5]octane-2-carboxylic acid
• 英文别名: 2-chloro-6-cyano-6-[3-(cyclopentyloxy)-4-methoxyphenyl]-1-oxaspiro[2.5]octane-2-carboxylic acid；2-Chloro-6-cyano-6-(3-cyclopentyloxy-4-methoxyphenyl)-1-oxaspiro[2.5]octane-2-carboxylic acid
• 化学式: C₂₁H₂₄ClNO₅
• 分子量: 405.878
• InChiKey: OOLNHSCKYYQXFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-chloro-6-cyano-6-(3-cyclopentyloxy-4-methoxyphenyl)-1-oxospiro[2.5]octane-2-carboxylic acid 在 sodium chloride 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 3.5h， 以59%的产率得到cilomilast
  参考文献：
  名称：

  A Practical Synthesis of the PDE4 Inhibitor, SB-207499, from a Cyclohexanone Precursor

  摘要：

  The synthesis of SB-207499 is described. Investigation and development of new strategies for the homologation of ketone, 4-cyano-4-[3-(cyclopentyloxy)-4-(methoxyphenyl)]-cyclohexan-1-one 2 are described which produce SB-207499. Our ultimate route of synthesis to SB-207499 is robust and operationally simple and produces the final drug substance in good yield and purity.

  DOI：

  10.1021/op025584z
• 作为产物：
  描述：

  methyl 2-chloro-6-cyano-6-(3-cyclopentyloxy-4-methoxyphenyl)-1-oxospiro[2.5]octane-2-carboxylate 在 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 0.25h， 以85%的产率得到2-chloro-6-cyano-6-(3-cyclopentyloxy-4-methoxyphenyl)-1-oxospiro[2.5]octane-2-carboxylic acid
  参考文献：
  名称：

  A Practical Synthesis of the PDE4 Inhibitor, SB-207499, from a Cyclohexanone Precursor

  摘要：

  The synthesis of SB-207499 is described. Investigation and development of new strategies for the homologation of ketone, 4-cyano-4-[3-(cyclopentyloxy)-4-(methoxyphenyl)]-cyclohexan-1-one 2 are described which produce SB-207499. Our ultimate route of synthesis to SB-207499 is robust and operationally simple and produces the final drug substance in good yield and purity.

  DOI：

  10.1021/op025584z

文献信息

• Process for preparing acids via alpha-chloroepoxy esters
  申请人：SmithKline Beecham Corporation

  公开号：US20040220424A1

  公开（公告）日：2004-11-04

  This invention relates to a method for preparing certain acids of formula (I) via a chloroepoxy ester, which are useful as phosphodiesterase 4 inhibitors. 1

  本发明涉及一种通过氯氧环酯制备式(I)某些酸的方法，其作为磷酸二酯酶4抑制剂具有用途。
• PROCESS FOR PREPARING ACIDS VIA ALPHA-CHLOROEPOXY ESTERS
  申请人：SmithKline Beecham Corporation

  公开号：EP1200394A1

  公开（公告）日：2002-05-02
• EP1200394A4
  申请人：——

  公开号：EP1200394A4

  公开（公告）日：2004-12-01
• [EN] PROCESS FOR PREPARING ACIDS VIA ALPHA-CHLOROEPOXY ESTERS<br/>[FR] ELABORATION D'ACIDES PAR L'INTERMEDIAIRE D'ESTERS ALPHA-CHLOROEPOXY
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2001010822A1

  公开（公告）日：2001-02-15

  This invention relates to a method for preparing certain acids of formula (I) via a chloroepoxy ester, which are useful as phosphodiesterase 4 inhibitors.
• A Practical Synthesis of the PDE4 Inhibitor, SB-207499, from a Cyclohexanone Precursor
  作者：Neil F. Badham、Jian-Hao Chen、Paul G. Cummings、Philip C. Dell'Orco、Ann M. Diederich、Ann M. Eldridge、Wilford L. Mendelson、Robert J. Mills、Vance J. Novack、Mark A. Olsen、Abu M. Rustum、Kevin S. Webb、Shawn Yang

  DOI：10.1021/op025584z

  日期：2003.1.1

  The synthesis of SB-207499 is described. Investigation and development of new strategies for the homologation of ketone, 4-cyano-4-[3-(cyclopentyloxy)-4-(methoxyphenyl)]-cyclohexan-1-one 2 are described which produce SB-207499. Our ultimate route of synthesis to SB-207499 is robust and operationally simple and produces the final drug substance in good yield and purity.