(1S,2S,5R,8R)-5-phenylspiro[4-oxa-6-azatricyclo[6.3.0.02,6]undecane-10,1'-cyclopropane]-7-one | 597569-39-6

• 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: (1S,2S,5R,8R)-5-phenylspiro[4-oxa-6-azatricyclo[6.3.0.02,6]undecane-10,1'-cyclopropane]-7-one
• CAS: 597569-39-6
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: JJUMUPUULUQELU-DSJMHWKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2S,5R,8R)-5-phenylspiro[4-oxa-6-azatricyclo[6.3.0.02,6]undecane-10,1'-cyclopropane]-7-one 在 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 [(3S,3aS,6aR)-spiro[2,3,3a,4,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-5,1'-cyclopropane]-3-yl]methanol
  参考文献：
  名称：

  [3+2] Cycloaddition of trimethylenemethane (TMM) to α,β-unsaturated γ-lactam. Preparation of 5,5-fused proline surrogates

  摘要：

  Unsaturated lactam derived from (S)-pyroglutaminol undergoes a totally stereoselective cycloaddition reaction with (2-(acetoxymethyl)-3-allyl)trimethylsilane in the presence of Pd(P(OiPr)(3))(4) in refluxing toluene. This step was efficiently used to introduced the 5,5-fused framework desired for the preparation of novel proline surrogates. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(03)01191-2
• 作为产物：
  描述：

  (3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one 在 {(i-C3H7O)3P}4Pd 、 diethylzinc 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 13.0h， 生成 (1S,2S,5R,8R)-5-phenylspiro[4-oxa-6-azatricyclo[6.3.0.02,6]undecane-10,1'-cyclopropane]-7-one
  参考文献：
  名称：

  [3+2] Cycloaddition of trimethylenemethane (TMM) to α,β-unsaturated γ-lactam. Preparation of 5,5-fused proline surrogates

  摘要：

  Unsaturated lactam derived from (S)-pyroglutaminol undergoes a totally stereoselective cycloaddition reaction with (2-(acetoxymethyl)-3-allyl)trimethylsilane in the presence of Pd(P(OiPr)(3))(4) in refluxing toluene. This step was efficiently used to introduced the 5,5-fused framework desired for the preparation of novel proline surrogates. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(03)01191-2

文献信息

• [3+2] Cycloaddition of trimethylenemethane (TMM) to α,β-unsaturated γ-lactam. Preparation of 5,5-fused proline surrogates
  作者：Edwin Jao、Stephane Bogen、Anil K Saksena、Viyyoor Girijavallabhan

  DOI：10.1016/s0040-4039(03)01191-2

  日期：2003.6

  Unsaturated lactam derived from (S)-pyroglutaminol undergoes a totally stereoselective cycloaddition reaction with (2-(acetoxymethyl)-3-allyl)trimethylsilane in the presence of Pd(P(OiPr)(3))(4) in refluxing toluene. This step was efficiently used to introduced the 5,5-fused framework desired for the preparation of novel proline surrogates. (C) 2003 Published by Elsevier Science Ltd.