tetrahydro-3,3-bis(3-iodopropyl)-2(2H)-pyranone | 163012-23-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: tetrahydro-3,3-bis(3-iodopropyl)-2(2H)-pyranone
• 英文别名: 3,3-bis(3-iodopropyl)oxan-2-one
• CAS: 163012-23-5
• 化学式: C₁₁H₁₈I₂O₂
• 分子量: 436.072
• InChiKey: APAIHWINGQEDBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tetrahydro-3,3-bis(3-iodopropyl)-2(2H)-pyranone 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以97%的产率得到cis-5-(3-hydroxypropyl)bicyclo<3.3.0>octan-1-ol
  参考文献：
  名称：

  Sequenced Reactions with Samarium(II) Iodide. Tandem Intramolecular Nucleophilic Acyl Substitution/Intramolecular Barbier Cyclizations

  摘要：

  Samarium(II) iodide has been employed to promote a tandem intramolecular nucleophilic acyl substitution/intramolecular Barbier cyclization sequence, generating bicyclic and tricyclic ring systems in excellent yield and high diastereoselectivity. Additionally, a highly versatile ring expansion-cyclization sequence allows entry into several different naturally occurring tricyclic ring systems containing seven- and eight-membered rings.

  DOI：

  10.1021/ja00118a007
• 作为产物：
  描述：

  α,α-diallyl-δ-valerolactone 在 bis(cyclohexanyl)borane 、 sodium acetate 、 一氯化碘 作用下， 生成 tetrahydro-3,3-bis(3-iodopropyl)-2(2H)-pyranone
  参考文献：
  名称：

  Sequenced Reactions with Samarium(II) Iodide. Tandem Intramolecular Nucleophilic Acyl Substitution/Intramolecular Barbier Cyclizations

  摘要：

  Samarium(II) iodide has been employed to promote a tandem intramolecular nucleophilic acyl substitution/intramolecular Barbier cyclization sequence, generating bicyclic and tricyclic ring systems in excellent yield and high diastereoselectivity. Additionally, a highly versatile ring expansion-cyclization sequence allows entry into several different naturally occurring tricyclic ring systems containing seven- and eight-membered rings.

  DOI：

  10.1021/ja00118a007