6-(Iodomethyl)tricyclo<5.3.0.0^2,6>-3-decanone | 131321-92-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(Iodomethyl)tricyclo<5.3.0.0^2,6>-3-decanone
• 英文别名: 6-(Iodomethyl)tricyclo[5.3.0.02,6]decan-3-one
• CAS: 131321-92-1
• 化学式: C₁₁H₁₅IO
• 分子量: 290.144
• InChiKey: SERCQPKZGFBFIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-(Iodomethyl)tricyclo<5.3.0.0^2,6>-3-decanone 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以90%的产率得到6-Methylenebicyclo<5.3.0>-3-decanone
  参考文献：
  名称：

  Free Radical Fragmentation of [2 + 2] Photoadduct Derivatives. Formal Synthesis of Pentalenene

  摘要：

  A series of [2 + 2] photoadducts 3a-d are converted to cyclobutylcarbinyl iodides 6a-d. Free radical fragmentation of the iodides yields bicyclo[x.y.0] carbon skeletons 7a-d which are present in a variety of natural products. Application of this methodology to terpenoid synthesis is illustrated by the preparation of unsaturated ketone 19 in only six steps (33% overall yield). As 19 has been converted to pentalenene (1) this constitutes a formal synthesis of the angular triquinane sesquiterpenoid.

  DOI：

  10.1021/jo00112a043
• 作为产物：
  描述：

  methyl spiro[1,3-dioxolane-2,8'-tricyclo[5.3.0.02,6]decane]-1'-carboxylate 在 咪唑 、 lithium aluminium tetrahydride 、 oxonium 、 碘 、 三苯基膦 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 6-(Iodomethyl)tricyclo<5.3.0.0^2,6>-3-decanone
  参考文献：
  名称：

  Free radical fragmentation of derivatives of [2 + 2] photoadducts

  摘要：

  DOI：

  10.1016/s0040-4039(00)98009-2

文献信息

• Lange, Gordon L.; Gottardo, Christine, Synthetic Communications, 1990, vol. 20, # 10, p. 1473 - 1479
  作者：Lange, Gordon L.、Gottardo, Christine

  DOI：——

  日期：——
• LANGE, GORDON L.;GOTTARDO, CHRISTINE, SYNTH. COMMUN., 20,(1990) N0, C. 1473-1479
  作者：LANGE, GORDON L.、GOTTARDO, CHRISTINE

  DOI：——

  日期：——
• LANGE, GORDON L.;GOTTARDO, CHRISTINE, TETRAHEDRON LETT., 31,(1990) N2, C. 5985-5988
  作者：LANGE, GORDON L.、GOTTARDO, CHRISTINE

  DOI：——

  日期：——
• Free Radical Fragmentation of [2 + 2] Photoadduct Derivatives. Formal Synthesis of Pentalenene
  作者：Gordon L. Lange、Christine Gottardo

  DOI：10.1021/jo00112a043

  日期：1995.4

  A series of [2 + 2] photoadducts 3a-d are converted to cyclobutylcarbinyl iodides 6a-d. Free radical fragmentation of the iodides yields bicyclo[x.y.0] carbon skeletons 7a-d which are present in a variety of natural products. Application of this methodology to terpenoid synthesis is illustrated by the preparation of unsaturated ketone 19 in only six steps (33% overall yield). As 19 has been converted to pentalenene (1) this constitutes a formal synthesis of the angular triquinane sesquiterpenoid.
• Free radical fragmentation of derivatives of [2 + 2] photoadducts
  作者：Gordon L Lange、Christine Gottardo

  DOI：10.1016/s0040-4039(00)98009-2

  日期：1990.1