(3aR,5S,6S,6aR)-2,2-Dimethyl-6-((E)-3-phenyl-allyloxy)-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde | 402559-34-6

• 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: (3aR,5S,6S,6aR)-2,2-Dimethyl-6-((E)-3-phenyl-allyloxy)-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde
• 英文别名: (3aR,5S,6S,6aR)-2,2-dimethyl-6-[(E)-3-phenylprop-2-enoxy]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde
• CAS: 402559-34-6
• 化学式: C₁₇H₂₀O₅
• 分子量: 304.343
• InChiKey: VOASWZYZHOYXGH-CBIXMBKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,5S,6S,6aR)-2,2-Dimethyl-6-((E)-3-phenyl-allyloxy)-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde 在 盐酸羟胺 、 sodium methylate 、 chloroamine-T 作用下， 以 甲醇 、 水 为溶剂， 生成 (3R,3aR,5aS,5bR,8aR,9aR)-7,7-dimethyl-3-phenyl-3a,4,5a,5b,8a,9a-hexahydro-3H-[1,3]dioxolo[4'',5'':4',5']oxolo[2',3':5,6]oxino[4,3-c]isoxazole
  参考文献：
  名称：

  Synthesis, high-resolution NMR spectroscopic analysis, and single-crystal X-ray diffraction of isoxazoline tetracycles

  摘要：

  Three isoxazoline tetracycles were obtained enantiomerically pure by intramolecular 1,3-dipolar cycloaddition. The characterization of the new compounds was performed by high-resolution H-1 and C-13 NMR spectroscopy. The relative configuration of the new chiral centers was determined by NOESY experiments and confirmed by single-crystal X-ray structural analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00258-6
• 作为产物：
  描述：

  (2'E)-3-O-(3'-phenyl-2'-propenyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 sodium periodate 、 水 、 碳酸氢钠 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 (3aR,5S,6S,6aR)-2,2-Dimethyl-6-((E)-3-phenyl-allyloxy)-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde
  参考文献：
  名称：

  糖衍生的烯丙基醚的“非模板位点”分子内氮酮环加成（INC）反应—呋喃并吡喃的取代作用和合成研究

  摘要：

  将在末端烯烃碳中心具有一个或两个取代基的糖衍生的烯丙基醚进行分子内硝酮环加成（INC）反应，生成双环[4.3.0]系统。产物形成的排他性可以归因于取代基的作用。

  DOI：

  10.1016/s0040-4039(01)01889-5

文献信息

• Increased formation of oxepanes in non-aqueous medium in the cycloaddition of 3-O-allyl-1,2-isopropylidenefuranose N-Ph nitrones
  作者：Seema Datta、Madhumita Nath、Sandip Chowdhury、Anup Bhattacharjya

  DOI：10.1016/j.tetlet.2008.03.014

  日期：2008.4

  Cycloaddition of 3-O-allyl-1,2-isopropylidene N-Ph nitrones afforded appreciably increased yields of oxepanes compared to the corresponding N-Me or N-Bn nitrones. Higher yields permitted some useful further transformations of the oxepanes. (c) 2008 Elsevier Ltd. All rights reserved.
• ‘Off-template site’ intramolecular nitrone cycloaddition (INC) reactions on sugar-derived allylic ethers—a study on the substituent effect and synthesis of furano-pyrans
  作者：G.V.M Sharma、K Ravinder Reddy、A Ravi Sankar、A.C Kunwar

  DOI：10.1016/s0040-4039(01)01889-5

  日期：2001.12

  Sugar-derived allylic ethers having one or two substituents on the terminal olefinic carbon centre were subjected to intramolecular nitrone cycloaddition (INC) reactions resulting in bicyclo[4.3.0] systems. The exclusiveness of product formation may be attributed to the effect of substituents.

  将在末端烯烃碳中心具有一个或两个取代基的糖衍生的烯丙基醚进行分子内硝酮环加成（INC）反应，生成双环[4.3.0]系统。产物形成的排他性可以归因于取代基的作用。
• Synthesis, high-resolution NMR spectroscopic analysis, and single-crystal X-ray diffraction of isoxazoline tetracycles
  作者：Mirta L Fascio、Angel Alvarez-Larena、Norma B D'Accorso

  DOI：10.1016/s0008-6215(02)00258-6

  日期：2002.11

  Three isoxazoline tetracycles were obtained enantiomerically pure by intramolecular 1,3-dipolar cycloaddition. The characterization of the new compounds was performed by high-resolution H-1 and C-13 NMR spectroscopy. The relative configuration of the new chiral centers was determined by NOESY experiments and confirmed by single-crystal X-ray structural analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.