(E)-(R)-1-iodo-2-methylhepta-1,6-dien-4-ol | 936445-64-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-(R)-1-iodo-2-methylhepta-1,6-dien-4-ol
• 英文别名: (1E,4R)-1-iodo-2-methylhepta-1,6-dien-4-ol
• CAS: 936445-64-6
• 化学式: C₈H₁₃IO
• 分子量: 252.095
• InChiKey: UUYRCMBEKMKJGH-HYDMIIDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (E)-(R)-1-iodo-2-methylhepta-1,6-dien-4-ol 在 sodium periodate 、 四氧化锇 、 camphor-10-sulfonic acid 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 32.75h， 生成 (5S,E)-8-iodo-5-((4-methoxybenzyl)oxy)-7-methylocta-1,7-dien-3-ol
  参考文献：
  名称：

  An Efficient and Stereoselective Synthesis of the Monomeric Counterpart of Marinomycin A

  摘要：

  The monomeric counterpart of marinomycin A, an antitumor-antibiotic marine natural product, was synthesized efficiently in 11 steps from the commercially available ethyl (R)-(-)-3-hydroxybutyrate. The strategy was highlighted by a crucial regio- and stereoselective cross-metathesis to form the C20-C21 double bond, enantioselective allyltitanations to control the configuration of the C17, C23, and C25 stereogenic centers, and a stereocontrolled construction of the tetraene moiety based on an original Horner-Wadsworth-Emmons olefination followed by a Pd-catalyzed cross-coupling.

  DOI：

  10.1021/ol070240k
• 作为产物：
  描述：

  (E)-4-iodo-3-methylbut-3-en-1-ol 在 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (E)-(R)-1-iodo-2-methylhepta-1,6-dien-4-ol
  参考文献：
  名称：

  An Efficient and Stereoselective Synthesis of the Monomeric Counterpart of Marinomycin A

  摘要：

  The monomeric counterpart of marinomycin A, an antitumor-antibiotic marine natural product, was synthesized efficiently in 11 steps from the commercially available ethyl (R)-(-)-3-hydroxybutyrate. The strategy was highlighted by a crucial regio- and stereoselective cross-metathesis to form the C20-C21 double bond, enantioselective allyltitanations to control the configuration of the C17, C23, and C25 stereogenic centers, and a stereocontrolled construction of the tetraene moiety based on an original Horner-Wadsworth-Emmons olefination followed by a Pd-catalyzed cross-coupling.

  DOI：

  10.1021/ol070240k

文献信息

• Synthesis of the Monomeric Counterpart of Marinomycin A
  作者：Dominique Amans、Laurianne Bareille、Véronique Bellosta、Janine Cossy

  DOI：10.1021/jo900945x

  日期：2009.10.16

  An efficient and highly convergent synthesis of the monomeric counterpart of the antitumor-antibiotic marine natural product marinomycin A was achieved by using optically active titanium complexes to control the configuration of the stereogenic centers, a highly stereo- and regioselective cross-metathesis to generate the (E)-configured C20-C21 double bond, and a Horner-Wadsworth-Emmons olefination followed by a Pd-catalyzed Stille cross-coupling to construct the tetraene moiety.