cis-(2S,5S)-2-(tert-butyl)-5-phenyl-5-(cyclohexyl)-1,3-dioxolan-4-one | 268216-67-7

• 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: cis-(2S,5S)-2-(tert-butyl)-5-phenyl-5-(cyclohexyl)-1,3-dioxolan-4-one
• 英文别名: Cis-(2S,5S)-2-(tert-butyl)-5-phenyl-5-(cyclohexyl)1,3-dioxolan-4-one；(2S,5S)-2-tert-butyl-5-cyclohexyl-5-phenyl-1,3-dioxolan-4-one
• CAS: 268216-67-7
• 化学式: C₁₉H₂₆O₃
• 分子量: 302.414
• InChiKey: CICIFEMCFDCMNM-IEBWSBKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-(2S,5S)-2-(tert-butyl)-5-phenyl-5-(cyclohexyl)-1,3-dioxolan-4-one 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以104 g的产率得到(S)-2-环己基-2-苯基乙醇酸
  参考文献：
  名称：

  A large-scale asymmetric synthesis of (S)-cyclohexylphenyl glycolic acid

  摘要：

  A practical asymmetric synthesis of (S)-cyclohexylphenyl glycolic acid has been demonstrated at pilot scale. The key step is the asymmetric aldol reaction using the Seebach approach of self-replication of stereochemistry. (S)-Mandelic acid was converted into (2S,5S)-3 in >99/1 diastereomeric ratio. The dioxolone (2S,5S)-3 was then subjected to aldol conditions to give the aldol intermediate (2S,5R)-5 in 91% yield with >99.5/0.5 diastereomeric ratio. The aldol product was converted to the desired hydroxy acid. (S)-CHPGA, in three steps with only one isolation in high yield (95%) and high purity. (C) 200 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.036
• 作为产物：
  描述：

  cis-(2S,5S)-2-(tert-butyl)-5-phenyl-5-(cyclohex-1-ene)-1,3-dioxolan-4-one 在 palladium-carbon 作用下， 以 甲醇 为溶剂， 以94%的产率得到cis-(2S,5S)-2-(tert-butyl)-5-phenyl-5-(cyclohexyl)-1,3-dioxolan-4-one
  参考文献：
  名称：

  US6180823

  摘要：

  公开号：

文献信息

• Chiral Mandelic Acid Template Provides a Highly Practical Solution for (<i>S</i>)-Oxybutynin Synthesis
  作者：Paul T. Grover、Nandkumar N. Bhongle、Stephen A. Wald、Chris H. Senanayake

  DOI：10.1021/jo005562f

  日期：2000.9.1
• STEREOSELECTIVE PROCESS FOR PREPARING (CYCLO)ALKYL PHENYLGLYCOLIC ACIDS
  申请人：Sepracor Inc.

  公开号：EP1127043A1

  公开（公告）日：2001-08-29
• US6180823B1
  申请人：——

  公开号：US6180823B1

  公开（公告）日：2001-01-30
• US6376684B1
  申请人：——

  公开号：US6376684B1

  公开（公告）日：2002-04-23
• [EN] STEREOSELECTIVE PROCESS FOR PREPARING (CYCLO)ALKYL PHENYLGLYCOLIC ACIDS<br/>[FR] PROCEDE STEREOSELECTIF DE PREPARATION D'ACIDES (CYCLO)ALKYLPHENYLGLYCOLIQUES
  申请人：SEPRACOR INC

  公开号：WO2000027786A1

  公开（公告）日：2000-05-18

  A process for preparing an alkyl phenylglycolic acid is disclosed. It follows the sequence of condensing a substituted acetaldehyde with mandelic acid to provide a 5-phenyl-1,3-dioxolan-4-one, which is condensed with an alkyl ketone or aldehyde to provide a 5-(1-hydroxyalkyl)-5-phenyl-1,3-dioxolan-4-one, which is dehydrated to a 5-(1-alkenyl)-5-phenyl-1,3-dioxolan-4-one. The 5-(1-alkenyl)-5-phenyl-1,3-dioxolan-4-one may be hydrolyzed and reduced to an α-alkylphenylglycolic acid or the hydrolysis and reduction steps may be reversed. The process enables the production of single enantiomers of cyclohexylphenylglycolic acid (CHPGA). An analogous process for racemic CHPGA is disclosed employing racemic mandelic acid and acetone. Novel intermediates in the process are also disclosed.