(3~{R})-1,1-bis(oxidanylidene)thiolan-3-ol | 874013-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: (3~{R})-1,1-bis(oxidanylidene)thiolan-3-ol
• 英文别名: (3R)-1,1-dioxothiolan-3-ol
• CAS: 874013-02-2
• 化学式: C₄H₈O₃S
• mdl: MFCD00154867
• 分子量: 136.172
• InChiKey: AMXKVIWWXBYXRS-SCSAIBSYSA-N

物化性质

• 沸点：
  382.0±35.0 °C(Predicted)
• 密度：
  1.475±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (3~{R})-1,1-bis(oxidanylidene)thiolan-3-ol 在 吡啶 作用下， 以100%的产率得到Acetic acid (R)-1,1-dioxo-tetrahydro-1λ⁶-thiophen-3-yl ester
  参考文献：
  名称：

  Enzymatic kinetic resolution of 1,1-dioxo-2,3-dihydro-1H-1λ6-thiophen-3-ol via temporary derivatisation

  摘要：

  Following the thio-conjugate addition of (+/-)-9, its enantiomers were extremely efficiently discriminated using Novozym 435 (R). The thio-differentiating unit may then be removed either under reductive conditions, using Raney nickel, or following an oxidation-elimination sequence. In this manner enantioenriched derivatives of 1,1-dioxo-2,3-dihydro-1H-1 lambda(6)-thiophen-3-ol 9 may be accessed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.153
• 作为产物：
  描述：

  (3S,4S)-4-benzylsulfanyl-1,1-dioxothiolan-3-ol 在 镍 作用下， 以 乙醇 为溶剂， 以95%的产率得到(3~{R})-1,1-bis(oxidanylidene)thiolan-3-ol
  参考文献：
  名称：

  Enzymatic kinetic resolution of 1,1-dioxo-2,3-dihydro-1H-1λ6-thiophen-3-ol via temporary derivatisation

  摘要：

  Following the thio-conjugate addition of (+/-)-9, its enantiomers were extremely efficiently discriminated using Novozym 435 (R). The thio-differentiating unit may then be removed either under reductive conditions, using Raney nickel, or following an oxidation-elimination sequence. In this manner enantioenriched derivatives of 1,1-dioxo-2,3-dihydro-1H-1 lambda(6)-thiophen-3-ol 9 may be accessed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.153

文献信息

• Synthesis of chiral hydroxythiolanes as potential catalysts for asymmetric organozinc additions to carbonyl compounds
  作者：Piotr Kie?basi?ski、Ma?gorzata Albrycht、Marian Miko?ajczyk、Micha? W. Wieczorek、Wies?aw R. Majzner、Agnieszka Filipczak、Piotr Cio?kiewicz

  DOI：10.1002/hc.20076

  日期：——

  give a chiral monoacetate with ee up to 36%. After its oxidation two diastereomeric sulfoxides were obtained which were separated by chromatography. The crystalline one was subjected to X-ray analysis and its absolute configuration was determined as 1S, 3S, 4R. All the optically active products were checked as potential catalysts for asymmetric addition of diethylzinc to benzaldehyde. However, they

  旋光性 3-羟基硫杂环戊烷由 L-天冬氨酸立体定向合成，氧化得到两种非对映体 S-氧化物，通过色谱分离并确定其构型。以天然(+)-(R,R)-酒石酸为原料，首次立体定向合成了C2-对称反式-(R,R)-3,4-二羟基硫杂环戊烷。还获得并表征了其一些单官能化衍生物及其 S-氧化物。以类似的方式从内消旋酒石酸中获得内消旋-顺-3,4-二羟基硫杂环戊烷，并通过脂肪酶促进的乙酰化或相应的 O,O'-二乙酰衍生物的水解进行去对称化，得到手性单乙酸酯ee 高达 36%。氧化后得到两种非对映体亚砜，通过色谱法将其分离。对晶体进行 X 射线分析，确定其绝对构型为 1S、3S、4R。所有光学活性产物都被检查为二乙基锌不对称加成到苯甲醛的潜在催化剂。然而，它们被证明具有非常低的催化活性：产物的产率在 10-90% 的范围内，但 ee 仅高达 10%。得出的结论是，在这种类型的反应中，羟基硫化物（亚砜）部分既不
• Enzymatic kinetic resolution of 1,1-dioxo-2,3-dihydro-1H-1λ6-thiophen-3-ol via temporary derivatisation
  作者：Ben S. Morgan、Stanley M. Roberts、Paul Evans

  DOI：10.1016/j.tetlet.2006.05.153

  日期：2006.7

  Following the thio-conjugate addition of (+/-)-9, its enantiomers were extremely efficiently discriminated using Novozym 435 (R). The thio-differentiating unit may then be removed either under reductive conditions, using Raney nickel, or following an oxidation-elimination sequence. In this manner enantioenriched derivatives of 1,1-dioxo-2,3-dihydro-1H-1 lambda(6)-thiophen-3-ol 9 may be accessed. (c) 2006 Elsevier Ltd. All rights reserved.