O-allyl N-2-{5-(6,6-dichlorobicyclo[3.1.0]hexan-1-yl)benzo[d][1,3]dioxol-6-yl}ethyl carbamate | 889115-24-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: O-allyl N-2-{5-(6,6-dichlorobicyclo[3.1.0]hexan-1-yl)benzo[d][1,3]dioxol-6-yl}ethyl carbamate
• 英文别名: prop-2-enyl N-[2-[6-(6,6-dichloro-1-bicyclo[3.1.0]hexanyl)-1,3-benzodioxol-5-yl]ethyl]carbamate
• CAS: 889115-24-6
• 化学式: C₁₉H₂₁Cl₂NO₄
• 分子量: 398.286
• InChiKey: ZPUQIQLIPZDQQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-allyl N-2-{5-(6,6-dichlorobicyclo[3.1.0]hexan-1-yl)benzo[d][1,3]dioxol-6-yl}ethyl carbamate 在 四(三苯基膦)钯 5,5-二甲基-1,3-环己二酮 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 9.0h， 生成 2-(1'-Chlorospiro[7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-5,6'-cyclohexene]-6-yl)ethanol
  参考文献：
  名称：

  New Protocols for the Assembly of the Tetracyclic Framework Associated with the Aromatic Erythrina Alkaloids

  摘要：

  Treatment of the anion derived from the ring-fused gem-dichlorocyclopropane 4c with silver tetrafluoroborate afforded the spirocyclic compound 17 in 74% yield. Product 17 was readily converted, over three steps, into the beta-iodoethyl derivative 20 and treatment of this latter compound with n-Bu3SnH then afforded, in 93% yield and via a radical addition/elimination sequence, compound 2 incorporating the ABCD framework of the aromatic erythrina alkaloids.

  DOI：

  10.1021/ol060642c
• 作为产物：
  描述：

  5-bromo-6-(2-methoxyvinyl)benzo[d][1,3]dioxole 在 吡啶 、 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 锂硼氢 、 叠氮化锂 、 苄基三乙基氯化铵 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 71.5h， 生成 O-allyl N-2-{5-(6,6-dichlorobicyclo[3.1.0]hexan-1-yl)benzo[d][1,3]dioxol-6-yl}ethyl carbamate
  参考文献：
  名称：

  New Protocols for the Assembly of the Tetracyclic Framework Associated with the Aromatic Erythrina Alkaloids

  摘要：

  Treatment of the anion derived from the ring-fused gem-dichlorocyclopropane 4c with silver tetrafluoroborate afforded the spirocyclic compound 17 in 74% yield. Product 17 was readily converted, over three steps, into the beta-iodoethyl derivative 20 and treatment of this latter compound with n-Bu3SnH then afforded, in 93% yield and via a radical addition/elimination sequence, compound 2 incorporating the ABCD framework of the aromatic erythrina alkaloids.

  DOI：

  10.1021/ol060642c

文献信息

• New Protocols for the Assembly of the Tetracyclic Framework Associated with the Aromatic Erythrina Alkaloids
  作者：Pauline C. Stanislawski、Anthony C. Willis、Martin G. Banwell

  DOI：10.1021/ol060642c

  日期：2006.5.1

  Treatment of the anion derived from the ring-fused gem-dichlorocyclopropane 4c with silver tetrafluoroborate afforded the spirocyclic compound 17 in 74% yield. Product 17 was readily converted, over three steps, into the beta-iodoethyl derivative 20 and treatment of this latter compound with n-Bu3SnH then afforded, in 93% yield and via a radical addition/elimination sequence, compound 2 incorporating the ABCD framework of the aromatic erythrina alkaloids.