2,2-dimethyl-3-(1-naphthyl)-3-oxo-propanal | 71023-68-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2-dimethyl-3-(1-naphthyl)-3-oxo-propanal
• 英文别名: 2-Methyl-2-(1-naphthoyl)-propanal；2,2-Dimethyl-3-naphthalen-1-yl-3-oxopropanal
• CAS: 71023-68-2
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: LWKYDMHBZNKCRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-3-(1-naphthyl)-3-oxo-propanal 在 samarium diiodide 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 生成 ((1R,2S)-2-Hydroxy-3,3-dimethyl-2-naphthalen-1-yl-cyclopropyl)-acetic acid benzyl ester
  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：

  2,2-dimethyl-1-naphthalen-1-yl-3-pyrrolidin-1-ium-1-ylidenepropan-1-one;chloride 、 盐酸 以73%的产率得到
  参考文献：
  名称：

  KUHLMEY S.-R.; ADOLPH H.; RIETH K.; OPITZ G., LIEBIGS ANN. CHEM., 1979, NO 5, 617-627

  摘要：

  DOI：

文献信息

• Kuhlmey,S.-R. et al., Liebigs Annalen der Chemie, 1979, p. 617 - 627
  作者：Kuhlmey,S.-R. et al.

  DOI：——

  日期：——
• 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.
• KUHLMEY S.-R.; ADOLPH H.; RIETH K.; OPITZ G., LIEBIGS ANN. CHEM., 1979, NO 5, 617-627
  作者：KUHLMEY S.-R.、 ADOLPH H.、 RIETH K.、 OPITZ G.

  DOI：——

  日期：——