S-phenyl 3,3-dimethylthioacrylate | 70030-51-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: S-phenyl 3,3-dimethylthioacrylate
• 英文别名: S-phenyl 3-methylbut-2-enethioate
• CAS: 70030-51-2
• 化学式: C₁₁H₁₂OS
• 分子量: 192.282
• InChiKey: DUWSYFKVXXEFID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  S-phenyl 3,3-dimethylthioacrylate 在 aluminum oxide 、 正丁基锂 、 lithium diisopropyl amide 作用下， 以 乙醚 为溶剂， 反应 4.58h， 生成 蒿酮
  参考文献：
  名称：

  Reaction of ester enolates with nucleophiles. Stereocontrolled formation of ketone and aldehyde enolates

  摘要：

  DOI：

  10.1021/jo00243a050
• 作为产物：
  描述：

  美雌醇 在 三乙胺 作用下， 以 乙醚 为溶剂， 生成 S-phenyl 3,3-dimethylthioacrylate
  参考文献：
  名称：

  取代的丙二烯亚砜的新转化

  摘要：

  描述了三甲基甲硅烷基取代的烯丙基亚砜的制备和反应。丙二烯（2）在升温时重新排列，得到α，β-不饱和硫醇酯。

  DOI：

  10.1016/s0040-4039(00)85927-4

文献信息

• Conformationally restricted retinoids
  作者：Marcia I. Dawson、Peter D. Hobbs、Krzysztof Derdzinski、Rebecca L. S. Chan、John Gruber、Wanru Chao、Saundra Smith、Richard W. Thies、Leonard J. Schiff

  DOI：10.1021/jm00377a022

  日期：1984.11

  A series of conformationally restricted retinoids was synthesized and screened in two assays used to measure the ability of retinoids to control cell differentiation, namely, the reversal of keratinization in tracheal organ culture from vitamin A deficient hamsters and the inhibition of the induction of mouse epidermal ornithine decarboxylase by a tumor promoter. These compounds had bonds corresponding to selected bonds of the E-tetraene chain of retinoic acid (1) held in a planar cisoid conformation by inclusion in an aromatic ring. The meta-substituted analogue 3 of 4-[(E)-2-methyl-4-(2,6,6-trimethylcyclohexenyl)-1,3-butadienyl+ ++]benzoic acid (2) was far less active than 2 in both assays. In contrast, the vinyl homologue of 2 (4) and the 7,8-dihydro and 7,8-methano analogues (5 and 6) had activity comparable to that of 2. Analogues of 4-[(E)-2-(1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-6-naphthyl)propenyl] benzoic acid (7) were also screened. Replacement of the tetrahydronaphthalene ring of 7 by a benzonorbornenyl group (9) significantly reduced activity, as did removal of the vinylic methyl group from 9 (10). Replacement of the propenyl group of 9 by a cyclopropane ring (12) also reduced activity. Replacement of the tetrahydronaphthalene ring of 7 by 4,4-dimethyl-3,4-dihydro-2H-1-benzopyran and -benzothiopyran rings (13 and 14) also decreased activity. Inclusion of the 7,9 double bond system of 1 in an aromatic ring (15 and 16) reduced activity, whereas inclusion of the 5,7 double bond system in an aromatic ring enhanced activity (7 and 19). Inclusion of the 11,13 and 9,11,13 double bond systems in aromatic rings (2 and 18) also reduced activity below that of 1. Retinoic acid, 7, 13, 14, and 19 inhibited papilloma tumor formation in mice. Toxicity testing indicated that 7 was more toxic than 1, 13, 14, and 19, 19 was more toxic than 1, and 13 and 14 were less toxic than 1.
• Bachhawat et al., Journal of Biological Chemistry, 1956, vol. 219, p. 539,549
  作者：Bachhawat et al.

  DOI：——

  日期：——
• Wieland; Rueff, Angewandte Chemie, 1953, vol. 65, p. 186
  作者：Wieland、Rueff

  DOI：——

  日期：——
• CUTTING, I.;PARSONS, P. J., TETRAHEDRON LETT., 1983, 24, N 41, 4463-4464
  作者：CUTTING, I.、PARSONS, P. J.

  DOI：——

  日期：——
• FEHR, CHARLES;GALINDO, JOSE, J. ORG. CHEM., 53,(1988) N 8, 1828-1830
  作者：FEHR, CHARLES、GALINDO, JOSE

  DOI：——

  日期：——