(4R,5S)-indano[1,2-d]thiazolidine-2-thione | 1101186-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (4R,5S)-indano[1,2-d]thiazolidine-2-thione
• 英文别名: (3aR,8aS)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d]thiazole-2-thione；(3aS,8bR)-1,3a,4,8b-tetrahydroindeno[1,2-d][1,3]thiazole-2-thione
• CAS: 1101186-85-9
• 化学式: C₁₀H₉NS₂
• 分子量: 207.32
• InChiKey: VAQRMAZSLRVFGN-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R,5S)-indano[1,2-d]thiazolidine-2-thione 在 methyloxirane 作用下， 反应 48.0h， 以76%的产率得到(4R,5S)-indano[1,2-d]-1,3-thiazolidine-2-one
  参考文献：
  名称：

  Desulfurization–Oxygenation of Chiral 1,3-Thiazolidine-2-thiones and 1,3-Oxazolidine-2-thiones Using Propylene Oxide and Microwave Irradiation

  摘要：

  An efficient method for the desulfurization-oxygenation of 1,3-thiazolidine-2-thiones and 1,3-oxazolidine-2-thiones using propylene oxide and employing microwave irradiation is described. This strategy of oxygenation of the thiocarbonyl group provides an attractive methodology to prepare chiral 1,3-thiazolidin-2-ones and 1,3-oxazolidin-2-ones from the corresponding precursors in good yields.

  DOI：

  10.1055/s-0032-1317525
• 作为产物：
  描述：

  异戊酸酐 、 1,3a,4,8b-Tetrahydroindeno[1,2-d][1,3]thiazole-2-thione 在 (+)-苯并四咪唑 、 N,N-二异丙基乙胺 作用下， 以 氘代氯仿 为溶剂， 反应 2.0h， 生成 (4R,5S)-indano[1,2-d]thiazolidine-2-thione 、 2-methyl-1-((3aS,8aR)-2-thioxo-8,8a-dihydro-2H-indeno[1,2-d]thiazol-3(3aH)-yl)propan-1-one
  参考文献：
  名称：

  Kinetic Resolution of N-Acyl-Thiolactams via Catalytic Enantioselective Deacylation

  摘要：

  Methanolysis of N-acyl-thiazolidin-2-thiones and -oxazolidin-2-thiones in the presence of acyl transfer catalyst benzotetramisole (BTM) proceeds in a highly enantioselective fashion thus enabling kinetic resolution of these substrates.

  DOI：

  10.1021/ol401122g

文献信息

• Methods for the Preparation of Thiazolidinethione Indene-Based Chiral Auxiliaries
  申请人：Olivo Horacio F.

  公开号：US20100179330A1

  公开（公告）日：2010-07-15

  Methods for the preparation of indene-based thiazolidinethiones are provided comprising contacting 1-amino-2,3-dihydro-1H-inden-2-ol, or a substituted derivative thereof, with an acid under suitable reaction conditions to provide a first intermediate; and contacting the first intermediate with an alkali xanthate in the presence of an alkali hydroxide under suitable reaction conditions to provide a compound of formula (III), wherein R 1 -R 8 are defined herein.

  提供了一种制备基于茚的噻唑啉硫酮的方法，包括将1-氨基-2,3-二氢-1H-茚-2-醇或其取代衍生物与酸在适当的反应条件下接触，以提供第一中间体；并在适当的反应条件下将第一中间体与碱性黄原酸酯在碱性羟化物存在下接触，以提供式（III）的化合物， 其中R1-R8在此处定义。
• Diastereoselective Preparation of Substituted δ-Valerolactones. Synthesis of (3<i>R</i>,4<i>S</i>)- and (3<i>R</i>,4<i>R</i>)-Simplactones
  作者：Antonio Osorio-Lozada、Horacio F. Olivo

  DOI：10.1021/jo8025548

  日期：2009.2.6

  were achieved in 5 steps from N-acyl thiazolidinethione chiral auxiliaries. The syntheses feature a double diastereoselective acetate aldol reaction solely controlled by the chirality of the auxiliary. Highly diastereoselective aldol reactions with s-trioxane were also achieved with N-acyl thiazolidinethione auxiliaries and the stereochemistry of an aldol product confirmed by X-ray analysis.

  从N-酰基噻唑烷硫酮手性助剂分5步完成了辛内酯（3 R，4 S）-1和（3 R，4 R）-2的合成。合成具有双重非对映选择性乙酸羟醛醛缩反应，其仅由助剂的手性控制。用N-酰基噻唑烷硫酮辅助剂也可以实现与s-三恶烷的高度非对映选择性的羟醛反应，并且通过X射线分析证实了羟醛产物的立体化学。
• US8309738B2
  申请人：——

  公开号：US8309738B2

  公开（公告）日：2012-11-13
• Desulfurization–Oxygenation of Chiral 1,3-Thiazolidine-2-thiones and 1,3-Oxazolidine-2-thiones Using Propylene Oxide and Microwave Irradiation
  作者：Moises Romero-Ortega、Leticia Minor-Villar、Rodolfo Tello-Aburto、Horacio Olivo、Aydee Fuentes

  DOI：10.1055/s-0032-1317525

  日期：——

  An efficient method for the desulfurization-oxygenation of 1,3-thiazolidine-2-thiones and 1,3-oxazolidine-2-thiones using propylene oxide and employing microwave irradiation is described. This strategy of oxygenation of the thiocarbonyl group provides an attractive methodology to prepare chiral 1,3-thiazolidin-2-ones and 1,3-oxazolidin-2-ones from the corresponding precursors in good yields.
• Kinetic Resolution of <i>N</i>-Acyl-Thiolactams via Catalytic Enantioselective Deacylation
  作者：Valentina D. Bumbu、Xing Yang、Vladimir B. Birman

  DOI：10.1021/ol401122g

  日期：2013.6.7

  Methanolysis of N-acyl-thiazolidin-2-thiones and -oxazolidin-2-thiones in the presence of acyl transfer catalyst benzotetramisole (BTM) proceeds in a highly enantioselective fashion thus enabling kinetic resolution of these substrates.