1-[[2-(trimethylsilyl)ethyl]thio]pyrrolidine-2,5-dione | 1096711-42-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-[[2-(trimethylsilyl)ethyl]thio]pyrrolidine-2,5-dione
• 英文别名: 1-(2-Trimethylsilylethylsulfanyl)pyrrolidine-2,5-dione
• CAS: 1096711-42-0
• 化学式: C₉H₁₇NO₂SSi
• 分子量: 231.391
• InChiKey: WYVVKSKIWPNAAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[[2-(trimethylsilyl)ethyl]thio]pyrrolidine-2,5-dione 、 (6R)-6-[[(tert-butyldimethylsilyl)oxy]methyl]tetrahydro-2-methylpyrrolo[1,2-a]pyrazine-1,4,8(8aH)-trione 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以55%的产率得到(6R,8aR)-6-[[(tert-butyldimethylsilyl)oxy]methyl]tetrahydro-2-methyl-8a-[[2-(trimethylsilyl)ethyl]thio]pyrrolo[1,2-a]pyrazine-1,4,8(8aH)-trione
  参考文献：
  名称：

  Synthetic studies related to MPC1001: formation of a model epidithiodiketopiperazine

  摘要：

  A tricyclic epidithiodiketopiperazine was prepared having structural features related to the antitumor antibiotic MPC1001. The method is based on the use of the sulfenylating agent p-MeC6H4S(O-2)SCH2OSiMe2Bu-t to introduce two protected sulfur atoms in a sequential and stereocontrolled manner. Fluoride-induced deprotection to remove the CH2OSiMe2Bu-t units and release two sulfhydryl groups, followed by in situ oxidation, then generated the required bridged disulfide. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.055
• 作为产物：
  描述：

  丁二酰亚胺 、 2-(trimethylsilyl)ethanesulfenyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以2.20 g的产率得到1-[[2-(trimethylsilyl)ethyl]thio]pyrrolidine-2,5-dione
  参考文献：
  名称：

  Asymmetric Synthesis of the ABC-Ring System of the Antitumor Antibiotic MPC1001

  摘要：

  trans-4-Hydroxy-L-proline was converted into a tricyclic compound representing three contiguous rings of the anticancer antibiotic MPC1001. The tricyclic model contains the dihydrooxepin and diketopiperazine Subunits, as well as one of the Sulfur atoms of the natural product. The diketopiperazine unit was formed by a new method that involves cyclization of an enolate onto the carbonyl of a phenyl carbamate, and the dihydrooxepin ring was generated by using an acid-induced cyclization of an alcohol onto the beta-carbon of a vinylogous amide.

  DOI：

  10.1021/jo802344t

文献信息

• Synthesis of alkyl allenyl sulfoxides from thiosuccinimides via [2,3]-sigmatropic rearrangement
  作者：Adam B. Riddell、Michelle M. Michalski、Adrian L. Schwan

  DOI：10.1080/10426507.2022.2157829

  日期：——

  synthesis of a broad range of alkyl allenyl sulfoxides via the [2,3]-sigmatropic rearrangement difficult, alternative sources of electrophilic sulfur were explored. Examination of various N-sulfanylimides revealed that thiosuccinimides are a viable sulfur source for the synthesis of alkyl allenyl sulfoxides via the [2,3]-sigmatropic rearrangement. With the optimized conditions of excess propargyl alcohol

  摘要 由于烷基硫酰氯的不稳定性和替代反应模式使得通过 [2,3]-σ 重排合成范围广泛的烷基丙二烯亚砜变得困难，因此探索了亲电子硫的替代来源。对各种 N-sulfanylimides 的检查表明，硫代琥珀酰亚胺是通过 [2,3]-sigmatropic 重排合成烷基丙二烯亚砜的可行硫源。在 50 °C 氯仿中过量炔丙醇和碳酸钾的优化条件下，合成了多种烷基丙二烯亚砜，收率相当高（21-73%，21 个例子）。此外，丁炔-1,4-二醇可以在室温下用大量过量的二醇和化学计量的三乙胺在 THF 中选择性单官能化，形成 1-羟烷基丙二烯亚砜 (26–71%)。这些二醇也可以通过两个单独的 [2,3]-σ 重排进行双官能化，形成 2,3-二取代二烯 (53–66%)。如直接竞争实验所示，还发现烷基丙二烯亚砜的形成对炔丙基位置（3:1–100:0 比例）的较少取代具有选择性。三甲基甲硅烷基乙基硫代琥珀酰
• Synthetic studies related to MPC1001: formation of a model epidithiodiketopiperazine
  作者：Lihong Wang、Derrick L.J. Clive

  DOI：10.1016/j.tetlet.2012.01.055

  日期：2012.3

  A tricyclic epidithiodiketopiperazine was prepared having structural features related to the antitumor antibiotic MPC1001. The method is based on the use of the sulfenylating agent p-MeC6H4S(O-2)SCH2OSiMe2Bu-t to introduce two protected sulfur atoms in a sequential and stereocontrolled manner. Fluoride-induced deprotection to remove the CH2OSiMe2Bu-t units and release two sulfhydryl groups, followed by in situ oxidation, then generated the required bridged disulfide. (C) 2012 Elsevier Ltd. All rights reserved.
• Asymmetric Synthesis of the ABC-Ring System of the Antitumor Antibiotic MPC1001
  作者：Jianbiao Peng、Derrick L. J. Clive

  DOI：10.1021/jo802344t

  日期：2009.1.16

  trans-4-Hydroxy-L-proline was converted into a tricyclic compound representing three contiguous rings of the anticancer antibiotic MPC1001. The tricyclic model contains the dihydrooxepin and diketopiperazine Subunits, as well as one of the Sulfur atoms of the natural product. The diketopiperazine unit was formed by a new method that involves cyclization of an enolate onto the carbonyl of a phenyl carbamate, and the dihydrooxepin ring was generated by using an acid-induced cyclization of an alcohol onto the beta-carbon of a vinylogous amide.