tert-butyl 2-(4-cyanophenyl)-5,6-dimethoxy-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylate | 1236004-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: tert-butyl 2-(4-cyanophenyl)-5,6-dimethoxy-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylate
• 英文别名: tert-butyl 1-(4-cyanophenyl)-5,6-dimethoxy-2,7b-dihydro-1aH-cyclopropa[c]chromene-1-carboxylate
• CAS: 1236004-39-9
• 化学式: C₂₄H₂₅NO₅
• 分子量: 407.466
• InChiKey: FIHIYMYXPDYJDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  77.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(4-cyanophenyl)-5,6-dimethoxy-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylate 在 tin(II) trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到4-(7,8-dimethoxy-2-oxo-3,3a,4,9b-tetrahydro-2H-furo[3,2-c]chromen-3-yl)benzonitrile
  参考文献：
  名称：

  γ-Lactonizations of 2H-chromenes via cyclopropanation

  摘要：

  A two-step synthesis of tetrahydro-2H-furochromenones from 2H-chromenes is reported. The reaction of a series of tert-butyl 2-diazoacetate derivatives with 2H-chromenes, catalyzed by Rh(2)(OAc)(4), generated cyclopropane intermediates that rearranged to gamma-lactones on treatment with Sn(OTf)(2). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.059
• 作为产物：
  描述：

  6,7-dimethoxy-2H-chromene 、 Tert-butyl 2-(4-cyanophenyl)-2-diazoacetate 在 rhodium(II) acetate dimer 作用下， 以 二氯甲烷 为溶剂， 反应 5.08h， 以77%的产率得到tert-butyl 2-(4-cyanophenyl)-5,6-dimethoxy-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylate
  参考文献：
  名称：

  γ-Lactonizations of 2H-chromenes via cyclopropanation

  摘要：

  A two-step synthesis of tetrahydro-2H-furochromenones from 2H-chromenes is reported. The reaction of a series of tert-butyl 2-diazoacetate derivatives with 2H-chromenes, catalyzed by Rh(2)(OAc)(4), generated cyclopropane intermediates that rearranged to gamma-lactones on treatment with Sn(OTf)(2). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.059

文献信息

• γ-Lactonizations of 2H-chromenes via cyclopropanation
  作者：Sean Stokes、Ben Spears、Cameron Laseter、Bobby Barker、Keith T. Mead

  DOI：10.1016/j.tetlet.2010.05.059

  日期：2010.8

  A two-step synthesis of tetrahydro-2H-furochromenones from 2H-chromenes is reported. The reaction of a series of tert-butyl 2-diazoacetate derivatives with 2H-chromenes, catalyzed by Rh(2)(OAc)(4), generated cyclopropane intermediates that rearranged to gamma-lactones on treatment with Sn(OTf)(2). (C) 2010 Elsevier Ltd. All rights reserved.