3-Heptylhomoallyl alcohol | 125137-98-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-Heptylhomoallyl alcohol
• 英文别名: 3-Methylidenedecan-1-ol
• CAS: 125137-98-6
• 化学式: C₁₁H₂₂O
• 分子量: 170.295
• InChiKey: IKAKNWRPPLIUQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  3-Heptylhomoallyl alcohol 在 4-二甲氨基吡啶 、 C₄₂H₃₄F₁₀IrN₄⁽¹⁺⁾*F₆P^(1-) 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 24.0h， 生成 methyl 3-(1-((4-(tert-butyl)phenyl)sulfonyl)-3-heptylpyrrolidin-3-yl)propanoate
  参考文献：
  名称：

  Cyclic Amine Synthesis via Catalytic Radical‐Polar Crossover Cycloadditions

  摘要：

  The rapid assembly of valuable cyclic amine architectures in a single step from simple precursors has been recognized as an ideal platform in term of efficiency and sustainability. Although a vast number of studies regarding cyclic amine synthesis has been reported, new synthetic disconnection approaches are still high in demand. Herein, we report a catalytic radical‐polar crossover cycloaddition to cyclic amine synthesis triggered from primary sulfonamide under photoredox condition. This newly developed disconnection, comparable to established synthetic approaches, will allow to construct β, β‐disubstituted cyclic amine and β‐monosubstituted cyclic amine derivatives efficiently. This study highlights the unique utility of primary sulfonamide as a bifunctional reagent, which acts as a radical precursor and a nucleophile. The open‐shell methodology demonstrates broad tolerance to various functional groups, drug derivatives and natural products in an economically and sustainable fashion.

  DOI：

  10.1002/anie.202401671
• 作为产物：
  描述：

  3-溴-3-丁烯醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 1,2-双(二苯基膦)乙烷氯化镍 作用下， 以 四氢呋喃 为溶剂， 生成 3-Heptylhomoallyl alcohol
  参考文献：
  名称：

  Cyclic Amine Synthesis via Catalytic Radical‐Polar Crossover Cycloadditions

  摘要：

  The rapid assembly of valuable cyclic amine architectures in a single step from simple precursors has been recognized as an ideal platform in term of efficiency and sustainability. Although a vast number of studies regarding cyclic amine synthesis has been reported, new synthetic disconnection approaches are still high in demand. Herein, we report a catalytic radical‐polar crossover cycloaddition to cyclic amine synthesis triggered from primary sulfonamide under photoredox condition. This newly developed disconnection, comparable to established synthetic approaches, will allow to construct β, β‐disubstituted cyclic amine and β‐monosubstituted cyclic amine derivatives efficiently. This study highlights the unique utility of primary sulfonamide as a bifunctional reagent, which acts as a radical precursor and a nucleophile. The open‐shell methodology demonstrates broad tolerance to various functional groups, drug derivatives and natural products in an economically and sustainable fashion.

  DOI：

  10.1002/anie.202401671

文献信息

• One-pot conversions of (silylmethyl)cyclopropanes to homoallylic alcohols and 1,4-diols based on haloborane-induced ring opening
  作者：Ilhyong Ryu、Akira Hirai、Haruhisa Suzuki、Noboru Sonoda、Shinji Murai

  DOI：10.1021/jo00292a001

  日期：1990.3
• RYU, ILHYONG;HIRAI, AKIRA;SUZUKI, HARUHISA;SONODA, NOBORU;MURAI, SHINJI, J. ORG. CHEM., 55,(1990) N, C. 1408-1410
  作者：RYU, ILHYONG、HIRAI, AKIRA、SUZUKI, HARUHISA、SONODA, NOBORU、MURAI, SHINJI

  DOI：——

  日期：——