(S)-1-(4-mesityl-2-thioxothiazolidin-3-yl)ethanone | 924265-91-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-1-(4-mesityl-2-thioxothiazolidin-3-yl)ethanone
• 英文别名: 1-[(4S)-2-sulfanylidene-4-(2,4,6-trimethylphenyl)-1,3-thiazolidin-3-yl]ethanone
• CAS: 924265-91-8
• 化学式: C₁₄H₁₇NOS₂
• 分子量: 279.427
• InChiKey: JFZFIIIZOZHHEY-GFCCVEGCSA-N

物化性质

• 沸点：
  416.2±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  77.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-(4-mesityl-2-thioxothiazolidin-3-yl)ethanone 在 2,6-二甲基吡啶 、 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (S)-1-((S)-4-mesityl-2-thioxothiazolidin-3-yl)-3-(triethylsilyloxy)hex-5-en-1-one
  参考文献：
  名称：

  Enantioselective Synthesis of the C1–C6 and C7–C23 Fragments of the Proposed Structure of Iriomoteolide 1a

  摘要：

  Synthesis of the C1-C6 and C7-C23 fragments of the proposed structure of Iriomoteolide 1a has been accomplished. Key steps include a cross metathesis to form the C15-C16 E olefin and a chelation controlled Grignard addition to form the tertiary alcohol at C14. Notably, 7 of the 9 stereocenters of the proposed structure have been set using various aldol reactions employing metallo enolates of thiazolidinethiones.

  DOI：

  10.1021/ol300785c
• 作为产物：
  描述：

  (S)-4-mesitylthiazolidine-2-thione 、 乙酰氯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到(S)-1-(4-mesityl-2-thioxothiazolidin-3-yl)ethanone
  参考文献：
  名称：

  Highly Selective Acetate Aldol Additions Using Mesityl-Substituted Chiral Auxiliaries

  摘要：

  Highly diastereoselective acetate aldol additions using chlorotitanium enolates of mesityl-substituted N-acetyloxazolidinethione and N-acetylthiazolidinethione auxiliaries are reported. These additions proceed in high yields and diastereoselectivities (93:7 to 98:2) for aliphatic, aromatic, and alpha,beta-unsaturated aldehydes. Double diastereoselective acetate aldol additions are also reported and are found to proceed in high yields and diastereoselectivities (90:10 to 97:3).

  DOI：

  10.1021/ol062688b

文献信息

• A Modular, Stereoselective Approach to Spiroketal Synthesis
  作者：Michael Crimmins、Adam Azman

  DOI：10.1055/s-0031-1290670

  日期：2012.6

  A highly convergent and flexible synthetic approach to stereochemically defined spiroketals is reported. Substituents can be incorporated at various positions around the spiroketal framework without significant disruption to the synthetic scheme. The approach has been exploited to prepare the spiroketal fragment of milbemycin β14.

  报告了一种高度收敛和灵活的立体化学定义的螺酮合成方法。取代基可以在 spiroketal 框架周围的不同位置掺入，而不会显着破坏合成方案。该方法已被用于制备米尔倍霉素 β14 的螺旋缩酮片段。
• Enantioselective Total Synthesis of (−)-Pironetin: Iterative Aldol Reactions of Thiazolidinethiones
  作者：Michael T. Crimmins、Anne-Marie R. Dechert

  DOI：10.1021/ol9003228

  日期：2009.4.2

  The enantioselective total synthesis of pironetin has been achieved in 11 steps from known aldehyde 2. The synthesis relies on the formation of 5 out of 6 stereocenters through titanium mediated iterative aldol reactions. Key steps in this synthesis include an acetal aldol reaction to establish the stereochemistry at C8 and C9, an acetate aldol reaction, and “Evans” syn aldol reaction.

  pironetin 的对映选择性全合成已从已知的醛 2 分 11 个步骤实现。该合成依赖于通过钛介导的迭代醛醇反应形成 6 个立体中心中的 5 个。该合成的关键步骤包括在 C8 和 C9 处建立立体化学的缩醛醛醇反应、乙酸醛醇醛反应和“Evans”合成醛醇反应。
• Highly Selective Acetate Aldol Additions Using Mesityl-Substituted Chiral Auxiliaries
  作者：Michael T. Crimmins、Mariam Shamszad

  DOI：10.1021/ol062688b

  日期：2007.1.1

  Highly diastereoselective acetate aldol additions using chlorotitanium enolates of mesityl-substituted N-acetyloxazolidinethione and N-acetylthiazolidinethione auxiliaries are reported. These additions proceed in high yields and diastereoselectivities (93:7 to 98:2) for aliphatic, aromatic, and alpha,beta-unsaturated aldehydes. Double diastereoselective acetate aldol additions are also reported and are found to proceed in high yields and diastereoselectivities (90:10 to 97:3).
• Enantioselective Synthesis of the C1–C6 and C7–C23 Fragments of the Proposed Structure of Iriomoteolide 1a
  作者：Michael T. Crimmins、Anne-Marie R. Dechert

  DOI：10.1021/ol300785c

  日期：2012.5.4

  Synthesis of the C1-C6 and C7-C23 fragments of the proposed structure of Iriomoteolide 1a has been accomplished. Key steps include a cross metathesis to form the C15-C16 E olefin and a chelation controlled Grignard addition to form the tertiary alcohol at C14. Notably, 7 of the 9 stereocenters of the proposed structure have been set using various aldol reactions employing metallo enolates of thiazolidinethiones.