benzyl 3-(1-formyl-cyclohexyl)-prop-2-enoate | 516493-78-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 3-(1-formyl-cyclohexyl)-prop-2-enoate
• 英文别名: benzyl (E)-3-(1-formylcyclohexyl)prop-2-enoate
• CAS: 516493-78-0
• 化学式: C₁₇H₂₀O₃
• 分子量: 272.344
• InChiKey: BASKIYWDDPJYDB-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 3-(1-formyl-cyclohexyl)-prop-2-enoate 在 samarium diiodide 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到((1S,2R)-2-Hydroxy-spiro[2.5]oct-1-yl)-acetic acid benzyl ester
  参考文献：
  名称：

  Diastereoselective SmI2-mediated cyclisation of δ-oxo-α,β-unsaturated esters to cyclopropanols

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(02)02437-1
• 作为产物：
  描述：

  1-(1,3-dithian-2-yl)cyclohexanecarboxaldehyde 在 2,4,6-三甲基吡啶 、 sodium hydride 、 碘甲烷 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 生成 benzyl 3-(1-formyl-cyclohexyl)-prop-2-enoate
  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

• SmI2-Mediated 3-exo-trig cyclisation of δ-oxo-α,β-unsaturated esters to cyclopropanols and derivatives
  作者：Sophie Bezzenine-Lafollée、Francois Guibé、Hélène Villar、Riadh Zriba

  DOI：10.1016/j.tet.2004.05.074

  日期：2004.8

  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.
• 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.