(3aS,5aR)-2,3,3a,4-tetrahydro-1H,5aH-5-oxa-10a,10b-diazacyclopenta[a]fluoren-10-one | 1341154-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (3aS,5aR)-2,3,3a,4-tetrahydro-1H,5aH-5-oxa-10a,10b-diazacyclopenta[a]fluoren-10-one
• 英文别名: (6S,9R)-8-oxa-1,2-diazatetracyclo[7.7.0.02,6.010,15]hexadeca-10,12,14-trien-16-one
• CAS: 1341154-37-7
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: PECYBMRNWVONAB-TVQRCGJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aS,5aR)-2,3,3a,4-tetrahydro-1H,5aH-5-oxa-10a,10b-diazacyclopenta[a]fluoren-10-one 在 三乙基硅烷 、 magnesium bis(monoperoxyphthalate)hexahydrate 、 双(三甲基硅烷基)氨基钾 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 64.0h， 生成 (R)-n-propyl-2,3-dihydro-1H-isoindolin-1-one
  参考文献：
  名称：

  A highly diastereoselective synthesis of isoindolinone-centered Meyers’ tetracyclic lactams. Application to the asymmetric synthesis of 3-alkylisoindolinones

  摘要：

  A new methodology for the asymmetric synthesis of C-3 alkylated isoindolinones has been developed through a novel extension of Meyers' lactamisation. The key polycyclic lactam precursor was prepared in high yield and high diastereoselectivity by a two step sequence involving phthalic anhydride and aminoprolinol. Metallation/alkylation followed by hydride reduction of the transient N-acylhydrazonium species and ultimate removal of the chiral auxiliary without a loss of stereochemical integrity completed the synthesis of the target compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.020
• 作为产物：
  描述：

  (2S)-1-氨基-2-吡咯甲醇 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 5.5h， 生成 (3aS,5aR)-2,3,3a,4-tetrahydro-1H,5aH-5-oxa-10a,10b-diazacyclopenta[a]fluoren-10-one
  参考文献：
  名称：

  A highly diastereoselective synthesis of isoindolinone-centered Meyers’ tetracyclic lactams. Application to the asymmetric synthesis of 3-alkylisoindolinones

  摘要：

  A new methodology for the asymmetric synthesis of C-3 alkylated isoindolinones has been developed through a novel extension of Meyers' lactamisation. The key polycyclic lactam precursor was prepared in high yield and high diastereoselectivity by a two step sequence involving phthalic anhydride and aminoprolinol. Metallation/alkylation followed by hydride reduction of the transient N-acylhydrazonium species and ultimate removal of the chiral auxiliary without a loss of stereochemical integrity completed the synthesis of the target compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.020

文献信息

• A highly diastereoselective synthesis of isoindolinone-centered Meyers’ tetracyclic lactams. Application to the asymmetric synthesis of 3-alkylisoindolinones
  作者：Vangelis Agouridas、Frédéric Capet、Axel Couture、Eric Deniau、Pierre Grandclaudon

  DOI：10.1016/j.tetasy.2011.07.020

  日期：2011.7

  A new methodology for the asymmetric synthesis of C-3 alkylated isoindolinones has been developed through a novel extension of Meyers' lactamisation. The key polycyclic lactam precursor was prepared in high yield and high diastereoselectivity by a two step sequence involving phthalic anhydride and aminoprolinol. Metallation/alkylation followed by hydride reduction of the transient N-acylhydrazonium species and ultimate removal of the chiral auxiliary without a loss of stereochemical integrity completed the synthesis of the target compounds. (C) 2011 Elsevier Ltd. All rights reserved.