α-Benzyloxy-α-methyl-γ-butyrolactone | 241473-73-4

• 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: α-Benzyloxy-α-methyl-γ-butyrolactone
• 英文别名: 3-Methyl-3-phenylmethoxyoxolan-2-one
• CAS: 241473-73-4
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: HTNSMTMBZTXOEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-Benzyloxy-α-methyl-γ-butyrolactone 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 生成 2-Benzyloxy-4-hydroxy-2-methyl-butyraldehyde
  参考文献：
  名称：

  Samarium(II)-mediated 4-exo trig ketyl-olefin cyclisation of unsaturated aldehydes. A general, stereoselective synthesis of functionalised cyclobutanols

  摘要：

  gamma,delta-Unsaturated aldehydes having a quaternary centre in either the a or beta-position, have been prepared from substituted gamma-butyrolactones and undergo efficient 4-exo-trig ketyl-olefin cyclisation on treatment with samarium(II) iodide to give functionalised cyclobutanols. In all cases cyclisation occurs with complete diastereocontrol to give anti-cyclobutanol products. In the cyclisation of substrate 4ab, significant stereochemical control is achieved at three contiguous chiral centres. Both unsaturated esters and vinyl sulfones have been employed as substrates in the reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00910-7
• 作为产物：
  描述：

  α-benzyloxy-γ-butyrolactone 、 碘甲烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.83h， 以68%的产率得到α-Benzyloxy-α-methyl-γ-butyrolactone
  参考文献：
  名称：

  Samarium(II)-mediated 4-exo-trig cyclisations of unsaturated aldehydes. A stereoselective approach to functionalised cyclobutanols

  摘要：

  γ,δ-不饱和醛具有完全取代的中心，无论是在α-还是β-位置，均是通过取代的γ-丁内酯制备的，并在处理时与锶(II)碘化物发生高效的4-exo-trig环化反应，生成功能化的环丁醇。在所有情况下，环化反应都以完全的非对映选择性进行，生成反式环丁醇产物。产物的立体化学已通过NOE和X射线晶体学研究得到确认。在具有双键上第三个取代基的底物的环化反应中，位于环外的新形成的第三个立体中心实现了显著的控制。讨论了该第三个中心的立体选择性的来源及其对共溶剂的显著依赖性。

  DOI：

  10.1039/a909549g

文献信息

• Samarium(II)-mediated 4-exo-trig cyclisations of unsaturated aldehydes. A stereoselective approach to functionalised cyclobutanols
  作者：Derek Johnston、Catherine F. McCusker、Kenneth Muir、David J. Procter

  DOI：10.1039/a909549g

  日期：——

  γ,δ-Unsaturated aldehydes having a fully substituted centre in either the α- or β-positions, have been prepared from substituted γ-butyrolactones and undergo efficient 4-exo-trig cyclisation on treatment with samarium(II) iodide to give functionalised cyclobutanols. In all cases cyclisation occurs with complete diastereocontrol to give anti-cyclobutanol products. The stereochemistry of the products has been confirmed by NOE and X-ray crystallographic studies. In the cyclisation of substrates having a third substituent on the double bond, α- to the ester, significant control is achieved at the third newly formed stereocentre lying outside the ring. The origin of the stereoselectivity at this third centre and its marked dependence on cosolvent are discussed.

  γ,δ-不饱和醛具有完全取代的中心，无论是在α-还是β-位置，均是通过取代的γ-丁内酯制备的，并在处理时与锶(II)碘化物发生高效的4-exo-trig环化反应，生成功能化的环丁醇。在所有情况下，环化反应都以完全的非对映选择性进行，生成反式环丁醇产物。产物的立体化学已通过NOE和X射线晶体学研究得到确认。在具有双键上第三个取代基的底物的环化反应中，位于环外的新形成的第三个立体中心实现了显著的控制。讨论了该第三个中心的立体选择性的来源及其对共溶剂的显著依赖性。
• Samarium(II)-mediated 4-exo trig ketyl-olefin cyclisation of unsaturated aldehydes. A general, stereoselective synthesis of functionalised cyclobutanols
  作者：Derek Johnston、Catherine M. McCusker、David J. Procter

  DOI：10.1016/s0040-4039(99)00910-7

  日期：1999.6

  gamma,delta-Unsaturated aldehydes having a quaternary centre in either the a or beta-position, have been prepared from substituted gamma-butyrolactones and undergo efficient 4-exo-trig ketyl-olefin cyclisation on treatment with samarium(II) iodide to give functionalised cyclobutanols. In all cases cyclisation occurs with complete diastereocontrol to give anti-cyclobutanol products. In the cyclisation of substrate 4ab, significant stereochemical control is achieved at three contiguous chiral centres. Both unsaturated esters and vinyl sulfones have been employed as substrates in the reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.