<3aR, 9bS>-(-)-1,3a-4,9a-tetrahydro-cis-3H-<1>benzopyrano<4,3-c>isoxazole | 169105-70-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: <3aR, 9bS>-(-)-1,3a-4,9a-tetrahydro-cis-3H-<1>benzopyrano<4,3-c>isoxazole
• 英文别名: (+)-1,3a,4,9b-tetrahydro-3H-[1]benzopyrano[4,3-c]isoxazole；(3aR,9bS)-3,3a,4,9b-tetrahydro-1H-chromeno[4,3-c][1,2]oxazole
• CAS: 169105-70-8
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: ZXMFDPAQTCFAEQ-XCBNKYQSSA-N

物化性质

• 沸点：
  268.7±50.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <3aR, 9bS>-(-)-1,3a-4,9a-tetrahydro-cis-3H-<1>benzopyrano<4,3-c>isoxazole 、 cis-2,3-epoxysuccinic anhydride 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis

  摘要：

  本文描述了琥珀酸和谷氨酸环状内消旋酐的一种新的高效去对称化方法，在大多数情况下提供了优异的产率和非对映选择性。通过将去对称化产物转化为单保护的1,4-二醇，展示了它们的衍生化能力。通过该方法在免疫抑制抗肿瘤天然产物雷帕霉素的全合成中关键片段的应用，证明了其普遍的合成实用性。

  DOI：

  10.1039/b813494d
• 作为产物：
  描述：

  1,3a-4,9a-tetrahydro-cis-3H-<1>benzopyrano<4,3-c>isoxazole 生成 <3aR, 9bS>-(-)-1,3a-4,9a-tetrahydro-cis-3H-<1>benzopyrano<4,3-c>isoxazole
  参考文献：
  名称：

  Highly efficient resolution of benzopyrano[4,3-c]isoxazolidine derivatives: Versatile chiral auxiliaries for asymmetric alkylation

  摘要：

  Benzopyrano[4,3-c]isoxazolidine derivatives, newly developed chiral auxiliaries for asymmetric alkylation, were synthesized and resolved in a unique manner. Resolution could be executed so efficiently that both enantiomers were obtained with a single resolving reagent in excellent yields.

  DOI：

  10.1016/0957-4166(95)00162-i

文献信息

• Abiko, Atsushi; Moriya, Osamu; Filla, Sandra A., Angewandte Chemie, 1995, vol. 107, # 7, p. 869 - 871
  作者：Abiko, Atsushi、Moriya, Osamu、Filla, Sandra A.、Masamune, Satoru

  DOI：——

  日期：——
• Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis
  作者：Amanda C. Evans、Deborah A. Longbottom、Masato Matsuoka、John E. Davies、Richard Turner、Vilius Franckevičius、Steven V. Ley

  DOI：10.1039/b813494d

  日期：——

  A new and efficient desymmetrisation of succinic and glutaric cyclic meso-anhydrides is described, providing excellent yields and diastereoselectivities in most cases. Derivatisation of the desymmetrised products is demonstrated by their conversion into mono-protected 1,4-diols. General synthetic utility of the method is established by its application towards a key fragment in the total synthesis of the immunosuppressant antitumour natural product, rapamycin.

  本文描述了琥珀酸和谷氨酸环状内消旋酐的一种新的高效去对称化方法，在大多数情况下提供了优异的产率和非对映选择性。通过将去对称化产物转化为单保护的1,4-二醇，展示了它们的衍生化能力。通过该方法在免疫抑制抗肿瘤天然产物雷帕霉素的全合成中关键片段的应用，证明了其普遍的合成实用性。
• Highly efficient resolution of benzopyrano[4,3-c]isoxazolidine derivatives: Versatile chiral auxiliaries for asymmetric alkylation
  作者：Atsushi Abiko、William M. Davis、Satoru Masamune

  DOI：10.1016/0957-4166(95)00162-i

  日期：1995.6

  Benzopyrano[4,3-c]isoxazolidine derivatives, newly developed chiral auxiliaries for asymmetric alkylation, were synthesized and resolved in a unique manner. Resolution could be executed so efficiently that both enantiomers were obtained with a single resolving reagent in excellent yields.