3-hydroxy-3-(methylthiomethyl)-2-methyl-2,3-dihydro-1H-isoindol-1-one | 143142-79-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-hydroxy-3-(methylthiomethyl)-2-methyl-2,3-dihydro-1H-isoindol-1-one
• 英文别名: 3-hydroxy-2-methyl-3-methylsulfanylmethyl-2,3-dihydroisoindol-1-one；3-hydroxy-2-methyl-3-(methylthiomethyl)isoindolin-1-one；3-Hydroxy-2-methyl-3-(methylsulfanylmethyl)isoindol-1-one
• CAS: 143142-79-4
• 化学式: C₁₁H₁₃NO₂S
• 分子量: 223.296
• InChiKey: FGYMAAQBTCBRQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-甲基邻苯二甲酰亚胺 、 二甲基硫 生成 3-hydroxy-3-(methylthiomethyl)-2-methyl-2,3-dihydro-1H-isoindol-1-one
  参考文献：
  名称：

  Sato, Yasuhiko; Wada, Masao; Nakai, Hideo, Heterocycles, 1983, vol. 20, # 1, p. 173

  摘要：

  DOI：

文献信息

• Synthesis of Sulfur-Containing Tricyclic Ring Systems by Means of Photoinduced Decarboxylative Cyclizations
  作者：Axel G. Griesbeck、Michael Oelgemöller、Johann Lex、Andreas Haeuseler、Michael Schmittel

  DOI：10.1002/1099-0690(200105)2001:10<1831::aid-ejoc1831>3.0.co;2-7

  日期：2001.5

  sulfuractivated and nonactivated species (13, 15) or irradiation of 1a under nonactivating conditions showed that the carboxylate anion in the position alpha to the electron-donating sulfur atom acts as a superior leaving group. This efficiency is drastically reduced for carboxylate anions in the alpha position. With the former substrates, the photochemical cyclization proceeds with high product yields. Quantum

  研究了一系列巯基乙酸和巯基丙酸衍生物的分子内和分子间光致电子转移反应。在分子间系列中，邻苯二甲酰亚胺烷基硫基烷基羧酸盐 1a-j 和 2 分别以高区域选择性转化为三环系统 3a-j 和 4。巯基乙酸和 2-巯基丙酸衍生底物 1a-g 和 2 易于环化，产率（60-98%）但非对映选择性低（1d 除外），而相应的 3-巯基丙酸衍生底物 1h-j长时间照射后得到相应的三环产物 3h-j，但产率低（11-20%）。分子间版本 - 即，作为电子受体的 N-甲基邻苯二甲酰亚胺 (5) 的光脱羧加成 - 使用巯基乙酸成功，2-巯基丙酸底物 6a-c 和加成产物 7a-c 以高产率 (57-90%) 获得。然而，使用 3-(甲基硫烷基)丙酸 (6d) 没有观察到添加。对于分子内（具有 8a-c）和分子间（具有 9 个）版本的巯基琥珀酸衍生物，脱羧的区域选择性以受控方式进行。硫活化和非活化物质之间的比较 (13
• Microphotochemistry: 4,4'-Dimethoxybenzophenone mediated photodecarboxylation reactions involving phthalimides
  作者：Oksana Shvydkiv、Kieran Nolan、Michael Oelgemöller

  DOI：10.3762/bjoc.7.121

  日期：——

  A series of 4,4'-dimethoxybenzophenone mediated intra- and intermolecular photodecarboxylation reactions involving phthalimides have been examined under microflow conditions. Conversion rates, isolated yields and chemoselectivities were compared to analogous reactions in a batch photoreactor. In all cases investigated, the microreactions gave superior results thus proving the superiority of microphotochemistry over conventional technologies.

  一系列4,4'-二甲氧基苯甲酮介导的分子内和分子间光脱羧反应涉及邻苯二甲酰亚胺在微流条件下进行了研究。将转化率、分离收率和化学选择性与批量光反应器中类似反应进行了比较。在所有研究案例中，微反应给出了更好的结果，从而证明了微光化学技术的优越性。
• Griesbeck, Axel G.; Oelgemöller, Michael, Synlett, 2000, # 1, p. 71 - 72
  作者：Griesbeck, Axel G.、Oelgemöller, Michael

  DOI：——

  日期：——
• Sato, Yasuhiko; Wada, Masao; Nakai, Hideo, Heterocycles, 1983, vol. 20, # 1, p. 173
  作者：Sato, Yasuhiko、Wada, Masao、Nakai, Hideo、Hatanaka, Yasumaru、Kanaoka, Yuichi

  DOI：——

  日期：——
• From Conventional to Microphotochemistry: Photodecarboxylation Reactions Involving Phthalimides
  作者：Oksana Shvydkiv、Sonia Gallagher、Kieran Nolan、Michael Oelgemöller

  DOI：10.1021/ol102184u

  日期：2010.11.19

  A series of acetone-sensitized photodecarboxylation reactions involving phthalimides have been investigated using conventional and microphotochemistry. Both, intra- and intermolecular transformations were compared. In all cases examined, the reactions performed in microreactors were superior in terms of conversions or isolated yields. These findings unambiguously prove the advantage of microphotochemistry over conventional photochemical techniques.