9,10-hexadecadien-8-ol | 386278-48-4

• 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: 9,10-hexadecadien-8-ol
• CAS: 386278-48-4
• 化学式: C₁₆H₃₀O
• 分子量: 238.414
• InChiKey: FTRAJQTVIJMRSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  9,10-hexadecadien-8-ol 在 吡啶 、 palladium diacetate 、 lithium bromide 作用下， 以 溶剂黄146 、 丙酮 为溶剂， 反应 25.0h， 生成 (6Z,8E)-7-bromo-6,8-hexadecadiene
  参考文献：
  名称：

  Palladium(II)-Catalyzed S_N2‘ Reactions of α-Allenic Acetates. Stereoconvergent Synthesis of (Z,E)-2-Bromo-1,3-dienes

  摘要：

  The reaction of acetylated a-allenic alcohols with LiBr in the presence of 1.5 mol % of Pd(OAc)(2) provides easy access to substituted (Z,E)-2-bromo-1,3-dienes in good yields with excellent diastereoselectivity. Both secondary and tertiary acetates as well as terminal and nonterminal allenes were studied to investigate the scope and the limitations of the reaction. A mechanism is proposed to clarify how a diastereomeric mixture of the starting compound is transformed into a single diastereomer of the product.

  DOI：

  10.1021/jo015950x
• 作为产物：
  描述：

  3-tetrahydropyranyloxyoct-1-yne 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 9.5h， 生成 9,10-hexadecadien-8-ol
  参考文献：
  名称：

  Palladium(II)-Catalyzed S_N2‘ Reactions of α-Allenic Acetates. Stereoconvergent Synthesis of (Z,E)-2-Bromo-1,3-dienes

  摘要：

  The reaction of acetylated a-allenic alcohols with LiBr in the presence of 1.5 mol % of Pd(OAc)(2) provides easy access to substituted (Z,E)-2-bromo-1,3-dienes in good yields with excellent diastereoselectivity. Both secondary and tertiary acetates as well as terminal and nonterminal allenes were studied to investigate the scope and the limitations of the reaction. A mechanism is proposed to clarify how a diastereomeric mixture of the starting compound is transformed into a single diastereomer of the product.

  DOI：

  10.1021/jo015950x

文献信息

• Practical Ruthenium-Catalyzed Cyclocarbonylation of Allenyl Alcohols in 2,4,6-Collidine Leading to α,β-Unsaturated Lactones: Concise Stereoselective Synthesis of (+)-Isomintlactone
  作者：Masayoshi Tsubuki、Kazunori Takahashi、Toshio Honda

  DOI：10.1021/jo8025127

  日期：2009.2.6

  We have found that ruthenium-catalyzed cyclocarbonylation of allenyl alcohols in 2,4,6-collidine under atmospheric pressure of carbon monoxide smoothly proceeds to afford alpha,beta-unsaturated five- and six-membered lactones in moderate to good yields. Furthermore, we have completed a highly stereoselective synthesis of (+)-isomintlactone by the cyclocarbonylation of allenyl alcohol using 2,4,6-collidine.
• Palladium(II)-Catalyzed S_N2‘ Reactions of α-Allenic Acetates. Stereoconvergent Synthesis of (<i>Z</i>,<i>E</i>)-2-Bromo-1,3-dienes
  作者：Attila Horváth、Jan-E. Bäckvall

  DOI：10.1021/jo015950x

  日期：2001.11.1

  The reaction of acetylated a-allenic alcohols with LiBr in the presence of 1.5 mol % of Pd(OAc)(2) provides easy access to substituted (Z,E)-2-bromo-1,3-dienes in good yields with excellent diastereoselectivity. Both secondary and tertiary acetates as well as terminal and nonterminal allenes were studied to investigate the scope and the limitations of the reaction. A mechanism is proposed to clarify how a diastereomeric mixture of the starting compound is transformed into a single diastereomer of the product.