3-[(2S,3R)-3-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]oxiran-2-yl]propanenitrile | 1351932-57-4

• 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: 3-[(2S,3R)-3-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]oxiran-2-yl]propanenitrile
• CAS: 1351932-57-4
• 化学式: C₁₉H₂₃NO₅
• 分子量: 345.395
• InChiKey: LUYXTGRXJXTVAD-FQESAXDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  73.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[(2S,3R)-3-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]oxiran-2-yl]propanenitrile 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (1R,7aS)-1-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one
  参考文献：
  名称：

  A practical one-pot radical-ionic sequence for the preparation of epoxides: application to the synthesis of unnatural polyhydroxylated alkaloids

  摘要：

  An efficient one-pot sequence for the preparation of epoxides from alpha-iodoesters or alpha-iodonitriles and allylic alcohols is described. This sequence is based on the use of iodine atom transfer reaction onto allylic alcohols followed by a ring closing epoxidation reaction of the halohydrin intermediates. The feasibility of this sequence is showcased in the synthesis of the perhydroaza-azulene, an unnatural analog of castanospermine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.042
• 作为产物：
  描述：

  (1R)-1-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]prop-2-en-1-ol 在 三乙基硼 、 氧气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 3-[(2S,3R)-3-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]oxiran-2-yl]propanenitrile
  参考文献：
  名称：

  A practical one-pot radical-ionic sequence for the preparation of epoxides: application to the synthesis of unnatural polyhydroxylated alkaloids

  摘要：

  An efficient one-pot sequence for the preparation of epoxides from alpha-iodoesters or alpha-iodonitriles and allylic alcohols is described. This sequence is based on the use of iodine atom transfer reaction onto allylic alcohols followed by a ring closing epoxidation reaction of the halohydrin intermediates. The feasibility of this sequence is showcased in the synthesis of the perhydroaza-azulene, an unnatural analog of castanospermine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.042

文献信息

• A practical one-pot radical-ionic sequence for the preparation of epoxides: application to the synthesis of unnatural polyhydroxylated alkaloids
  作者：Eduardo Peralta-Hernández、Omar Cortezano-Arellano、Alejandro Cordero-Vargas

  DOI：10.1016/j.tetlet.2011.10.042

  日期：2011.12

  An efficient one-pot sequence for the preparation of epoxides from alpha-iodoesters or alpha-iodonitriles and allylic alcohols is described. This sequence is based on the use of iodine atom transfer reaction onto allylic alcohols followed by a ring closing epoxidation reaction of the halohydrin intermediates. The feasibility of this sequence is showcased in the synthesis of the perhydroaza-azulene, an unnatural analog of castanospermine. (C) 2011 Elsevier Ltd. All rights reserved.