1-(1,3-dithian-2-yl)cyclohexanecarboxaldehyde | 516493-73-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: 1-(1,3-dithian-2-yl)cyclohexanecarboxaldehyde
• 英文别名: 1-(1,3-Dithian-2-yl)cyclohexane-1-carbaldehyde
• CAS: 516493-73-5
• 化学式: C₁₁H₁₈OS₂
• 分子量: 230.395
• InChiKey: YVSKWMGPUUZJSD-UHFFFAOYSA-N

物化性质

• 沸点：
  354.1±42.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1,3-dithian-2-yl)cyclohexanecarboxaldehyde 在 2,4,6-三甲基吡啶 、 samarium diiodide 、 sodium hydride 、 碘甲烷 作用下， 以 四氢呋喃 、 水 、 丙酮 、 叔丁醇 为溶剂， 生成
  参考文献：
  名称：

  SmI2-Mediated 3-exo-trig cyclisation of δ-oxo-α,β-unsaturated esters to cyclopropanols and derivatives

  摘要：

  In the presence of samarium diiodide and a proton source, delta-oxo-gamma,gamma-disubstituted-alpha,beta-unsaturated esters of general formula R-CO-C(R',R')-CH=CH-CO2Bn readily cyclise to trans-cyclopropanol products and/or lactones derived from the cis isomers. For R=aryl, good stereoselectivities (ca 90%) in favor of the alcohols are generally obtained while a mixture of alcohols and lactones is obtained with R=alkyl or H. For R=cyclopropyl, the lactone is exclusively obtained in more than 90% yield. A mechanistic rationalisation of these variations of diastereoselectivity is proposed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.074
• 作为产物：
  描述：

  4-(cyclohexylidenemethyl)morpholine 、 2-chloro-1,3-dithiane 在 水 作用下， 以33%的产率得到1-(1,3-dithian-2-yl)cyclohexanecarboxaldehyde
  参考文献：
  名称：

  SmI2-Mediated 3-exo-trig cyclisation of δ-oxo-α,β-unsaturated esters to cyclopropanols and derivatives

  摘要：

  In the presence of samarium diiodide and a proton source, delta-oxo-gamma,gamma-disubstituted-alpha,beta-unsaturated esters of general formula R-CO-C(R',R')-CH=CH-CO2Bn readily cyclise to trans-cyclopropanol products and/or lactones derived from the cis isomers. For R=aryl, good stereoselectivities (ca 90%) in favor of the alcohols are generally obtained while a mixture of alcohols and lactones is obtained with R=alkyl or H. For R=cyclopropyl, the lactone is exclusively obtained in more than 90% yield. A mechanistic rationalisation of these variations of diastereoselectivity is proposed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.074

文献信息

• Diastereoselective SmI2-mediated cyclisation of δ-oxo-α,β-unsaturated esters to cyclopropanols
  作者：Hélène Villar、François Guibé

  DOI：10.1016/s0040-4039(02)02437-1

  日期：2002.12

  In the presence of samarium diiodide and a proton source, delta-oxo-gamma,gamma-disubstitutcd-alpha, beta-unsaturated esters readily cyclise with complete diastereocontrol to give anti-cyclopropanol products. (C) 2002 Elsevier Science Ltd. All rights reserved.