Toluene-4-sulfonic acid (3aS,6aS)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]furan-(3E)-ylidenemethyl ester | 194468-86-5

• 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: Toluene-4-sulfonic acid (3aS,6aS)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]furan-(3E)-ylidenemethyl ester
• 英文别名: [(E)-[(3aS,6aS)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]furan-3-ylidene]methyl] 4-methylbenzenesulfonate
• CAS: 194468-86-5
• 化学式: C₁₅H₁₄O₅S
• 分子量: 306.339
• InChiKey: NNFLCPHXLLFLRJ-GANVNIMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid (3aS,6aS)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]furan-(3E)-ylidenemethyl ester 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 22.0~500.0 ℃ 、1.33 Pa 条件下， 反应 16.75h， 生成 (3E,3aS,6aS)-3-[[(2R)-4-methyl-5-oxo-2H-furan-2-yl]oxymethylidene]-4,6a-dihydro-3aH-cyclopenta[b]furan-2-one
  参考文献：
  名称：

  Use of Winterfeldt's template to control the C-2′ configuration in the synthesis of strigol-type compounds

  摘要：

  A route comprising (i) a cycloaddition reaction of citraconic anhydride with the Winterfeldt auxiliary, (ii) hydride reduction of the cycloadduct, (iii) a (formal) ether formation, and (iv) a cycloreversion reaction allows efficient stereocontrol at C-2' in the synthesis of strigol and its structural analogues. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00077-5
• 作为产物：
  描述：

  (+-)-cis-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 Toluene-4-sulfonic acid (3aS,6aS)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]furan-(3E)-ylidenemethyl ester
  参考文献：
  名称：

  Use of Winterfeldt's template to control the C-2′ configuration in the synthesis of strigol-type compounds

  摘要：

  A route comprising (i) a cycloaddition reaction of citraconic anhydride with the Winterfeldt auxiliary, (ii) hydride reduction of the cycloadduct, (iii) a (formal) ether formation, and (iv) a cycloreversion reaction allows efficient stereocontrol at C-2' in the synthesis of strigol and its structural analogues. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00077-5

文献信息

• Strigol and sorgolactone synthetic studies use of Winterfeldt's template to control the C-2′ configuration
  作者：Susanne Röhrig、Lothar Hennig、Matthias Findeisen、Peter Welzel、Dietrich Müller

  DOI：10.1016/s0040-4039(97)01228-8

  日期：1997.8

  A route comprising (i) a cycloaddition reaction of citraconic anhydride with the Winterfeldt auxiliary, (ii) hydride reduction of the cycloadduct, (iii) a (formal) ether formation, and (iv) a cycloreversion reaction allows efficient stereocontrol at C-2' in the synthesis of strigol and its structural analogues. (C) 1997 Elsevier Science Ltd.
• Use of Winterfeldt's template to control the C-2′ configuration in the synthesis of strigol-type compounds
  作者：Susanne Röhrig、Lothar Hennig、Matthias Findeisen、Peter Welzel、Dietrich Müller

  DOI：10.1016/s0040-4020(98)00077-5

  日期：1998.4

  A route comprising (i) a cycloaddition reaction of citraconic anhydride with the Winterfeldt auxiliary, (ii) hydride reduction of the cycloadduct, (iii) a (formal) ether formation, and (iv) a cycloreversion reaction allows efficient stereocontrol at C-2' in the synthesis of strigol and its structural analogues. (C) 1998 Elsevier Science Ltd. All rights reserved.