<(E)-5-bromo-2-methyl-2-pentenyl>methoxymethane | 149758-91-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <(E)-5-bromo-2-methyl-2-pentenyl>methoxymethane
• 英文别名: (E)-5-bromo-2-(methoxymethoxy)pent-2-ene；(2E)-5-Bromo-1-(methoxymethoxy)-2-methyl-2-pentene；(E)-5-bromo-1-(methoxymethoxy)-2-methylpent-2-ene
• CAS: 149758-91-8
• 化学式: C₈H₁₅BrO₂
• 分子量: 223.11
• InChiKey: YRRFRPOJAWLBBC-XBXARRHUSA-N

物化性质

• 沸点：
  238.8±30.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  <(E)-5-bromo-2-methyl-2-pentenyl>methoxymethane 在 六甲基磷酰三胺 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 14.0h， 生成 (E)-3-(5-(methoxymethoxy)-4-methylpent-3-enyl)-3-(phenylselanyl)-4,5-dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Total Synthesis of (±)-Bipinnatin J

  摘要：

  [GRAPHICS]The total synthesis of (+/-)-bipinnatin J was achieved through a concise route that features the use of a silver ion promoted S(N)1-type gamma-alkylation of a siloxyfuran and a diastereoselective Cr(II)-mediated macrocyclization to provide bipinnatin J (1), wherein the remote furanone stereocenter at C10 induced the relative stereochemistry of the two additional stereocenters.

  DOI：

  10.1021/ol053054s
• 作为产物：
  描述：

  5-溴-2-甲基-2-戊烯 在 叔丁基过氧化氢 、 selenium(IV) oxide 、 N,N-二异丙基乙胺 作用下， 以 癸烷 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 <(E)-5-bromo-2-methyl-2-pentenyl>methoxymethane
  参考文献：
  名称：

  Total Synthesis of (±)-Bipinnatin J

  摘要：

  [GRAPHICS]The total synthesis of (+/-)-bipinnatin J was achieved through a concise route that features the use of a silver ion promoted S(N)1-type gamma-alkylation of a siloxyfuran and a diastereoselective Cr(II)-mediated macrocyclization to provide bipinnatin J (1), wherein the remote furanone stereocenter at C10 induced the relative stereochemistry of the two additional stereocenters.

  DOI：

  10.1021/ol053054s

文献信息

• Studies directed toward the total synthesis of cerorubenic acid-III. 2. Analysis of the inability to realize D ring formation by means of extraannular Robinson annulation
  作者：Leo A. Paquette、Gilbert Y. Lassalle、Carl J. Lovely

  DOI：10.1021/jo00068a020

  日期：1993.7

  The possibility of achieving construction of the complete framework of cerorubenic acid-III by means of a highly convergent anionic oxy-Cope steP followed by extraannular Robinson annulation has been probed. To this end, the dithiane 10 and iodides 14 were prepared and merged via S(N)2 chemistry. The dianion derived from 15d added smoothly to beta,gamma-unsaturated ketone 5, and the resulting diastereomers 18b and 19b were separated and individually transformed into the diketone pairs 22 and 23. When these advanced intermediates failed to undergo the cyclization required for assembly of ring D, the ability of parent ketone 28 to undergo nucleophilic addition with various of nucleophiles was assessed. Although somewhat attenuated, the carbonyl group in this peculiar structural setting gives evidence of being adequately reactive.