3-(5-oxo-tetrahydro-[2]furyl)-propionyl chloride | 124468-90-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-(5-oxo-tetrahydro-[2]furyl)-propionyl chloride
• 英文别名: 3-(5-Oxo-tetrahydro-[2]furyl)-propionylchlorid；3-(5-Oxooxolan-2-yl)propanoyl chloride
• CAS: 124468-90-2
• 化学式: C₇H₉ClO₃
• 分子量: 176.6
• InChiKey: VFRLHAGWMXHLLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(5-oxo-tetrahydro-[2]furyl)-propionyl chloride 、 silver salt of 2-[(3S,4R)-3-[(1'R)-1-allyloxycarbonyloxyethyl]-4-mercapto-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester 生成 prop-2-enyl 2-[(3S,4R)-2-oxo-4-[3-(5-oxooxolan-2-yl)propanoylsulfanyl]-3-[(1R)-1-prop-2-enoxycarbonyloxyethyl]azetidin-1-yl]-2-(triphenyl-λ5-phosphanylidene)acetate
  参考文献：
  名称：

  CAPRARO, HANS-GEORG;FRANCOTTE, ERIC;KOHLER, BORIS;RIHS, GRETHY;SCHNEIDER,+, J. ANTIBIOTICS, 41,(1988) N 6, 759-770

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(5-oxotetrahydro-2-furanyl)propanoic acid 生成 3-(5-oxo-tetrahydro-[2]furyl)-propionyl chloride
  参考文献：
  名称：

  Asymmetric synthesis of 5- and 6-membered lactones from cyclic substrates bearing a C2-chiral auxiliary

  摘要：

  Optically active lactones were synthesized by a novel asymmetric synthesis in which enantiotopic groups remote from a prochiral center were effectively discriminated. The cyclic diamide alcohols bearing a C2-chiral auxiliary, (+)-[1,1'-binaphthyl]-2,2'-diamine (4), were designed and prepared such that the hydroxyl group should attack preferentially at one of the two carbonyl groups. By the catalytic action of trifluoroacetic acid, the substrates 6a,b and 19 were smoothly converted to the lactones 7a (71% de), 7b (97% de), and 20 (> 99% de), the configurations of which were determined to be R, S, and R, respectively. A naturally occurring pheromone, (R)-(+)-5-hexadecanolide (13), was synthesized optically pure from 7b. Transition-state models for the present asymmetric lactonization were constructed according to the stereoelectronic theory proposed by Deslongchamps. The stability of the models was assessed by MM2 calculation, and the direction of asymmetric induction thus calculated coincided with the experimental results.

  DOI：

  10.1021/jo00003a038

文献信息

• Bicyclische Thiaazaverbindungen
  申请人：CIBA-GEIGY AG

  公开号：EP0252885A1

  公开（公告）日：1988-01-13

  Verbindungen der Formel worin R₁ durch Hydroxy oder geschütztes Hydroxy substituiertes Niederalkyl ist, R₂ Carboxyl oder funktionell abgewandeltes Carboxyl bedeutet, A für Niederalkylen steht und R₃ einen über ein Ringkoh­lenstoffatom gebundenen, gegebenenfalls partiell ungesättigten Lactamylrest oder Lactonylrest darstellt, optische Isomere von Verbindungen der Formel I, Mischungen dieser optischen Isomere und Salze von Verbindungen der Formel I, die eine salzbildende Gruppe aufweisen, haben antibiotische Wirksamkeit. Die Verbindungen der Formel I werden nach an sich bekannten Verfahren hergestellt.

  式中的化合物 其中 R₁ 是被羟基或受保护的羟基取代的低级烷基，R₂ 是羧基或经功能修饰的羧基，A 是低级亚烷基，R₃ 是通过环碳原子键合的任选部分不饱和内酰胺基或内酰基，式 I 化合物的光学异构体、这些光学异构体的混合物以及具有成盐基团的式 I 化合物的盐具有抗生素活性。式 I 化合物通过本身已知的方法制备。
• An Intramolecular Rearrangement of 4-Benzoyloxycyclohexanone
  作者：Robert L. Clarke、William T. Hunter

  DOI：10.1021/ja01552a074

  日期：1958.10
• CAPRARO, HANS-GEORG;FRANCOTTE, ERIC;KOHLER, BORIS;RIHS, GRETHY;SCHNEIDER,+, J. ANTIBIOTICS, 41,(1988) N 6, 759-770
  作者：CAPRARO, HANS-GEORG、FRANCOTTE, ERIC、KOHLER, BORIS、RIHS, GRETHY、SCHNEIDER,+

  DOI：——

  日期：——
• Asymmetric synthesis of 5- and 6-membered lactones from cyclic substrates bearing a C2-chiral auxiliary
  作者：Yukio Yamamoto、Akio Sakamoto、Takaaki Nishioka、Junichi Oda、Yoshimasa Fukazawa

  DOI：10.1021/jo00003a038

  日期：1991.2

  Optically active lactones were synthesized by a novel asymmetric synthesis in which enantiotopic groups remote from a prochiral center were effectively discriminated. The cyclic diamide alcohols bearing a C2-chiral auxiliary, (+)-[1,1'-binaphthyl]-2,2'-diamine (4), were designed and prepared such that the hydroxyl group should attack preferentially at one of the two carbonyl groups. By the catalytic action of trifluoroacetic acid, the substrates 6a,b and 19 were smoothly converted to the lactones 7a (71% de), 7b (97% de), and 20 (> 99% de), the configurations of which were determined to be R, S, and R, respectively. A naturally occurring pheromone, (R)-(+)-5-hexadecanolide (13), was synthesized optically pure from 7b. Transition-state models for the present asymmetric lactonization were constructed according to the stereoelectronic theory proposed by Deslongchamps. The stability of the models was assessed by MM2 calculation, and the direction of asymmetric induction thus calculated coincided with the experimental results.