[¹⁸O]-(+/-)-1-(2'-chlorophenyl)but-3-en-1-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [¹⁸O]-(+/-)-1-(2'-chlorophenyl)but-3-en-1-ol
• 英文别名: 1-(2-chlorophenyl)but-3-en-1-(18O)ol
• 化学式: C₁₀H₁₁ClO
• 分子量: 184.65
• InChiKey: BFIIUQFVPDIOLQ-HVRMQOCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  溶剂黄146 、 丙醛 、 [¹⁸O]-(+/-)-1-(2'-chlorophenyl)but-3-en-1-ol 在 三甲基硅乙酸酯 、 三氟化硼乙醚 作用下， 以 环己烷 为溶剂， 反应 4.0h， 以39%的产率得到[¹⁸O]-4β-acetoxy-2β-(2'-chlorophenyl)-6β-ethyltetrahydropyran
  参考文献：
  名称：

  Prins Cyclizations:  Labeling Studies and Application to Natural Product Synthesis

  摘要：

  [GRAPHICS]The first syntheses of two natural products, catechols 1 and 2, isolated from Plectranthus sylvestris (labiatae), are reported. Oxygen-18 labeling studies support the proposed intermediacy of a stabilized benzylic cation in the acid-promoted cyclization of an aldehyde and benzylic homoallylic alcohol possessing an electron-rich aromatic ring, In contrast, with an electron-deficient aromatic ring the pathway via a benzylic cation is only minor.

  DOI：

  10.1021/ol020127o
• 作为产物：
  描述：

  氯丙烯镁 、 [¹⁸O]-2-chlorobenzaldehyde 以 四氢呋喃 为溶剂， 以72%的产率得到[¹⁸O]-(+/-)-1-(2'-chlorophenyl)but-3-en-1-ol
  参考文献：
  名称：

  Prins Cyclizations:  Labeling Studies and Application to Natural Product Synthesis

  摘要：

  [GRAPHICS]The first syntheses of two natural products, catechols 1 and 2, isolated from Plectranthus sylvestris (labiatae), are reported. Oxygen-18 labeling studies support the proposed intermediacy of a stabilized benzylic cation in the acid-promoted cyclization of an aldehyde and benzylic homoallylic alcohol possessing an electron-rich aromatic ring, In contrast, with an electron-deficient aromatic ring the pathway via a benzylic cation is only minor.

  DOI：

  10.1021/ol020127o

文献信息

• Prins Cyclizations:  Labeling Studies and Application to Natural Product Synthesis
  作者：Stuart R. Crosby、John R. Harding、Clare D. King、Gregory D. Parker、Christine L. Willis

  DOI：10.1021/ol020127o

  日期：2002.10.1

  [GRAPHICS]The first syntheses of two natural products, catechols 1 and 2, isolated from Plectranthus sylvestris (labiatae), are reported. Oxygen-18 labeling studies support the proposed intermediacy of a stabilized benzylic cation in the acid-promoted cyclization of an aldehyde and benzylic homoallylic alcohol possessing an electron-rich aromatic ring, In contrast, with an electron-deficient aromatic ring the pathway via a benzylic cation is only minor.