ethyl (E)-4-[(2,3-dihydro-2,2,4,4-tetramethyl-2H-1-benzothiopyran-6-yl)-1-propenyl]-2-methylbenzoate | 203855-87-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: ethyl (E)-4-[(2,3-dihydro-2,2,4,4-tetramethyl-2H-1-benzothiopyran-6-yl)-1-propenyl]-2-methylbenzoate
• 英文别名: ethyl 2-methyl-4-[(E)-2-(2,2,4,4-tetramethyl-3H-thiochromen-6-yl)prop-1-enyl]benzoate
• CAS: 203855-87-2
• 化学式: C₂₆H₃₂O₂S
• 分子量: 408.605
• InChiKey: SJCRWBRVXGHBHB-GHRIWEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (E)-4-[(2,3-dihydro-2,2,4,4-tetramethyl-2H-1-benzothiopyran-6-yl)-1-propenyl]-2-methylbenzoate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 ethyl (E)-4-[(2,3-dihydro-2,2,4,4-tetramethyl-2H-1-benzothiopyran-6-yl)-1-propenyl]-2-methylbenzoic acid
  参考文献：
  名称：

  Synthesis of Novel Heteroarotinoids with Receptor Activation Capabilities and Tgase Activity. Single Crystal Analysis of (E)-4-[(2,3-dihydro- 2,2,4,4,-tetramethyl-2H-1-benzo- [b]thiopyran-6-Yl)- 1-propenyl]-2-methylbenzoic Acid

  摘要：

  The syntheses of ethyl (E)-4-[(2,3-dihydro-2,2,4,4-tetramethyl-2H-1-benzo[b]thiopyran-6-yl)-1-propenyl]-2-methylbenzoate acid (1) and (E)-4- [(2,3-dihydro-2,2,4,4-tetramethyl-2H-1-benzo[b]thiopyran-6-yl)-l-pro-penyl]-2-methylbenzoic acid (2) haue been achieved. In comparison to ester 1, acid 2 exhibited greater efficacy in activating RARalpha, RARbeta, and RARgamma as well as greater potency in activating RARalpha and RARbeta. Interestingly, both the ester 1 and acid 2 exhibited nearly equal polency in activating RARgamma. Both compounds also inditced tissue transglutaininase (TGase) activity approximately 50% of the level induced by trans-retinoic acid. An X-ray diffraction analysis of (E)-2 revealed the aryl rings as nearly orthogonal [74.0(2)degrees] and a torsional angle of 46.5(2)degrees between the thiochroman group and the propenyl group. Conjugation between. such groups may not be a stringent requirement for receptor activation.

  DOI：

  10.1080/104265090507678
• 作为产物：
  描述：

  2,4-二甲基苯甲酸 在 chromium(VI) oxide 、 正丁基锂 、 硫酸 、 溶剂黄146 作用下， 以 乙醚 、 乙醇 、 正己烷 、 苯 为溶剂， 反应 106.75h， 生成 ethyl (E)-4-[(2,3-dihydro-2,2,4,4-tetramethyl-2H-1-benzothiopyran-6-yl)-1-propenyl]-2-methylbenzoate
  参考文献：
  名称：

  Synthesis of Novel Heteroarotinoids with Receptor Activation Capabilities and Tgase Activity. Single Crystal Analysis of (E)-4-[(2,3-dihydro- 2,2,4,4,-tetramethyl-2H-1-benzo- [b]thiopyran-6-Yl)- 1-propenyl]-2-methylbenzoic Acid

  摘要：

  The syntheses of ethyl (E)-4-[(2,3-dihydro-2,2,4,4-tetramethyl-2H-1-benzo[b]thiopyran-6-yl)-1-propenyl]-2-methylbenzoate acid (1) and (E)-4- [(2,3-dihydro-2,2,4,4-tetramethyl-2H-1-benzo[b]thiopyran-6-yl)-l-pro-penyl]-2-methylbenzoic acid (2) haue been achieved. In comparison to ester 1, acid 2 exhibited greater efficacy in activating RARalpha, RARbeta, and RARgamma as well as greater potency in activating RARalpha and RARbeta. Interestingly, both the ester 1 and acid 2 exhibited nearly equal polency in activating RARgamma. Both compounds also inditced tissue transglutaininase (TGase) activity approximately 50% of the level induced by trans-retinoic acid. An X-ray diffraction analysis of (E)-2 revealed the aryl rings as nearly orthogonal [74.0(2)degrees] and a torsional angle of 46.5(2)degrees between the thiochroman group and the propenyl group. Conjugation between. such groups may not be a stringent requirement for receptor activation.

  DOI：

  10.1080/104265090507678

文献信息

• Synthesis of Novel Heteroarotinoids with Receptor Activation Capabilities and Tgase Activity. Single Crystal Analysis of (<i>E</i>)-4-[(2,3-dihydro- 2,2,4,4,-tetramethyl-2<i>H</i>-1-benzo- [<i>b</i>]thiopyran-6-Yl)- 1-propenyl]-2-methylbenzoic Acid
  作者：K. Darrell Berlin、Shankar Subramanian、Chad M. Smith、Ali Tabatabai、Clinton D. Bryan、Brian Buettner、Steve Hale、Cynthia A. Wakefield、Doris M. Benbrook

  DOI：10.1080/104265090507678

  日期：2005.1.1

  The syntheses of ethyl (E)-4-[(2,3-dihydro-2,2,4,4-tetramethyl-2H-1-benzo[b]thiopyran-6-yl)-1-propenyl]-2-methylbenzoate acid (1) and (E)-4- [(2,3-dihydro-2,2,4,4-tetramethyl-2H-1-benzo[b]thiopyran-6-yl)-l-pro-penyl]-2-methylbenzoic acid (2) haue been achieved. In comparison to ester 1, acid 2 exhibited greater efficacy in activating RARalpha, RARbeta, and RARgamma as well as greater potency in activating RARalpha and RARbeta. Interestingly, both the ester 1 and acid 2 exhibited nearly equal polency in activating RARgamma. Both compounds also inditced tissue transglutaininase (TGase) activity approximately 50% of the level induced by trans-retinoic acid. An X-ray diffraction analysis of (E)-2 revealed the aryl rings as nearly orthogonal [74.0(2)degrees] and a torsional angle of 46.5(2)degrees between the thiochroman group and the propenyl group. Conjugation between. such groups may not be a stringent requirement for receptor activation.