octa-1,7-diene-4,5-diol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: octa-1,7-diene-4,5-diol
• 英文别名: (4R*,5R*)-octa-1,7-diene-4,5-diol；(4RS,5RS)-octa-1,7-diene-4,5-diol；1,7-octadiene-4,5-diol；(4R,5R)-octa-1,7-diene-4,5-diol
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: WNGQPXSRMCTUJF-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  octa-1,7-diene-4,5-diol 在 sodium tetrahydroborate 、 臭氧 作用下， 生成 (3R,4R)-3,4-isopropylidenehexane-1,6-diol
  参考文献：
  名称：

  Stereochemistry of palytoxin. Part 2. C1-C6, C47-C74, and C77-C83 segments

  摘要：

  DOI：

  10.1021/ja00389a099
• 作为产物：
  描述：

  (2R,3R,5R,6R)-2,3-Diallyl-5,6-diphenyl-[1,4]dioxane 在 氨 、 calcium 作用下， 以 乙醇 为溶剂， 以75%的产率得到octa-1,7-diene-4,5-diol
  参考文献：
  名称：

  Asymmetric synthesis using C2-symmetric diols: Use of (5R,6R)-3-acetoxy-5,6-diphenyl-1,4-dioxan-2-one as a chiral synthetic equivalent of 1,2-ethanediol 1,2-dicarbocation

  摘要：

  A new route to chiral diol systems has been developed based on double nucleophilic addition to the cationic ions fixed on a 6-membered ring system using chiral hydrobenzoin as an auxiliary.

  DOI：

  10.1016/0957-4166(95)00278-w

文献信息

• Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of <i>d,l</i> -1,2-Diols with Chiral Nucleophilic Catalysts
  作者：Kazuki Fujii、Koichi Mitsudo、Hiroki Mandai、Seiji Suga

  DOI：10.1002/adsc.201700057

  日期：2017.8.17

  An extremely efficient acylative kinetic resolution of d,l‐1,2‐diols in the presence of only 0.5 mol% of binaphthyl‐based chiral N,N‐4‐dimethylaminopyridine was developed (selectivity factor of up to 180). Several key experiments revealed that hydrogen bonding between the tert‐alcohol unit(s) of the catalyst and the 1,2‐diol unit of the substrate is critical for accelerating the rate of monoacylation

  在仅0.5 mol％的联萘基手性N，N -4-二甲基氨基吡啶存在下，开发了一种极有效的d，l - 1,2-二醇的酰基动力学拆分方法（选择性因子高达180）。几个关键实验表明，催化剂的叔醇单元与底物的1,2-二醇单元之间的氢键键合对于加快单酰化速率和实现高对映选择性至关重要。该催化体系可广泛应用于涉及外消旋无环和环状1,2-二醇且具有高选择性因子的底物。d，l-氢安息香和反式的动力学拆分数克级（10 g）的1,2-环己二醇也具有较高的选择性并在中等反应条件下进行：（i）催化剂负载量极低（0.1 mol％）; （ii）容易达到的低反应温度（0°C）；（iii）高底物浓度（1.0 M）；（iv）反应时间短（30分钟）。
• Stereoselective Construction of 2,7-Disubstituted <i>fused</i>-Bis Tetrahydrofuran Skeletons: Biomimetic-Type Synthesis and Biological Evaluation of (±)- and (−)-Aplysiallene and Their Derivatives
  作者：Maki Yamakawa、Takeshi Kurachi、Yusuke Yoshikawa、Mitsuhiro Arisawa、Yuichiro Okino、Kuniaki Suzuki、Hiromichi Fujioka

  DOI：10.1021/acs.joc.5b01882

  日期：2015.10.16

  A series of trans/trans and cis/cis fused-bis tetrahydrofuran compounds have been obtained stereoselectively in high yields via a one-pot operation involving the intramolecular haloetherification of (Z,Z)-diene diol 19a and (E,E)-diene disilylether 19d, respectively. This method was subsequently applied to the biomimetic-type synthesis of (+/-)- and (-)-aplysiallene. The inhibitory activities of these compounds and their bromodiene isomers toward Na+/K+ ATPase were determined in vitro, and gave IC50 values of approximately 15 mu M in all cases.
• Jiao, Peng; Kawasaki, Masanori; Yamamoto, Hisashi, Angewandte Chemie - International Edition, 2009, vol. 48, p. 3333 - 3336
  作者：Jiao, Peng、Kawasaki, Masanori、Yamamoto, Hisashi

  DOI：——

  日期：——
• Synthesis of Fused-Ring and Attached-Ring <i>bis</i>-Tetrahydrofurans via Pd-Catalyzed Carboetherification
  作者：Amanda F. Ward、John P. Wolfe

  DOI：10.1021/ol900594h

  日期：2009.5.21

  A five step-synthesis of fused bis-tetrahydrofurans and attached bis-tetrahydrofurans from butadiene diepoxide is described. Two sequential Pd-catalyzed carboetherification reactions between protected 1,2-diols and aryl/alkenyl bromides, each of which form both a C-O bond and a C-C bond, are used to generate the heterocyclic rings with >20:1 dr. Installation of different R-1 and R-2 groups is achieved in a straightforward fashion through use of different aryl or alkenyl bromide coupling partners.
• Bis Ring Closing Olefin Metathesis for the Synthesis of Unsaturated Polycyclic Ethers. O-Membered Ring Cyclization in Favor of C-Membered Ring Cyclization
  作者：Christophe Baylon、Marie-Pierre Heck、Charles Mioskowski

  DOI：10.1021/jo982098u

  日期：1999.4.1