(2R,3R)-ethyl 2-(3-methoxybenzyl)-3-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]pent-4-enoate | 959745-30-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,3R)-ethyl 2-(3-methoxybenzyl)-3-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]pent-4-enoate
• 英文别名: ethyl (2R,3R)-3-[(3S)-1,4-dioxaspiro[4.5]decan-3-yl]-2-[(3-methoxyphenyl)methyl]pent-4-enoate
• CAS: 959745-30-3
• 化学式: C₂₃H₃₂O₅
• 分子量: 388.504
• InChiKey: ZNSUXOVKKWZHEQ-NJDAHSKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  (2R,3R)-ethyl 2-(3-methoxybenzyl)-3-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]pent-4-enoate 在 氢氧化钾 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 以75%的产率得到(R)-5-hydroxymethyl-(R)-3-(3-methoxybenzyl)-(R)-4-vinyl-4,5-dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Convenient route to enantiopure substituted butyrolactones: application in a formal synthesis of both enantiomers of enterolactone

  摘要：

  A simple route for the synthesis of enantiopure substituted gamma-butyrolactones involving a highly diastereoselective alkylation of an enantiomerically pure substituted latent succinate ester is described. This route provides entry into both enantiomers of 3,4-disubstituted butyrolactones from a single enantiomer, 2,3-di-O-cyclohexylidine-R-(+)-glyceraldehyde. The synthetic potential of this methodology has been demonstrated by a formal synthesis of both enantiomers of enterolactone. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.103
• 作为产物：
  描述：

  3-甲氧基溴苄 、 (3S,2'S)-(1',4'-dioxa-spiro[4.5]dec-2'-yl)-pent-4-enoic acid ethyl ester 在 lithium diisopropyl amide 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以78%的产率得到(2R,3R)-ethyl 2-(3-methoxybenzyl)-3-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]pent-4-enoate
  参考文献：
  名称：

  Convenient route to enantiopure substituted butyrolactones: application in a formal synthesis of both enantiomers of enterolactone

  摘要：

  A simple route for the synthesis of enantiopure substituted gamma-butyrolactones involving a highly diastereoselective alkylation of an enantiomerically pure substituted latent succinate ester is described. This route provides entry into both enantiomers of 3,4-disubstituted butyrolactones from a single enantiomer, 2,3-di-O-cyclohexylidine-R-(+)-glyceraldehyde. The synthetic potential of this methodology has been demonstrated by a formal synthesis of both enantiomers of enterolactone. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.103

文献信息

• Convenient route to enantiopure substituted butyrolactones: application in a formal synthesis of both enantiomers of enterolactone
  作者：Manju Ghosh

  DOI：10.1016/j.tet.2007.08.103

  日期：2007.11

  A simple route for the synthesis of enantiopure substituted gamma-butyrolactones involving a highly diastereoselective alkylation of an enantiomerically pure substituted latent succinate ester is described. This route provides entry into both enantiomers of 3,4-disubstituted butyrolactones from a single enantiomer, 2,3-di-O-cyclohexylidine-R-(+)-glyceraldehyde. The synthetic potential of this methodology has been demonstrated by a formal synthesis of both enantiomers of enterolactone. (c) 2007 Elsevier Ltd. All rights reserved.