(E)-6-<(tetrahydro-2H-pyran-2-yl)oxy>-5-methyl-4-hexen-1-ol | 132298-85-2

• 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: (E)-6-<(tetrahydro-2H-pyran-2-yl)oxy>-5-methyl-4-hexen-1-ol
• 英文别名: (E)-6-[(tetrahydro-2H-pyran-2-yl)oxy]-5-methyl-4-hexen-1-ol；(E)-5-methyl-6-(oxan-2-yloxy)hex-4-en-1-ol
• CAS: 132298-85-2
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: NUFYUTIHFQBPSL-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-6-<(tetrahydro-2H-pyran-2-yl)oxy>-5-methyl-4-hexen-1-ol 在 四氯化碳 、 正丁基锂 、 四甲基乙二胺 、 氨 、 sodium acetate 、 sodium 、 lithium 、 sodium hydride 、 二异丁基氢化铝 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 三苯基膦 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 97.92h， 生成 (10E,14E)-(6S,7R,18S,19R)-6,18,19-tris(methoxymethoxy)-2,6,10,15,19,23-hexamethyltetracosa-2,10,14,22-tetraen-7-ol
  参考文献：
  名称：

  Total synthesis of the meso-triterpene polyether teurilene

  摘要：

  The first total synthesis of the triterpene ether teurilene (1) has been accomplished utilizing two vanadium(V)-catalyzed oxidation-cyclization reactions with different stereoselectivities. The synthesis involved stereoselective and step-by-step construction of 2,5-cis- and 2,5-trans-tetrahydrofuran rings, vanadium(V)-catalyzed oxidation of 4-substituted 4-en-1-ol 40 and subsequent cyclization of the resulting anti-epoxy alcohol 41, and a similar oxidation-cyclization of 5-substituted 4-en-1-ol 49 by way of syn-epoxy alcohol 50. This was followed by construction of a third tetrahydrofuran ring by more conventional means. An improved synthesis of 1, which featured direct formation of bis(tetrahydrofuran) 51 from squalene derivative 66 by simultaneous double oxidation-cyclization, was also accomplished.

  DOI：

  10.1021/jo00007a013
• 作为产物：
  描述：

  (E)-6-(Benzyloxy)-2-methyl-2-hexen-1-ol 在 氨 、 lithium 、 对甲苯磺酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.67h， 生成 (E)-6-<(tetrahydro-2H-pyran-2-yl)oxy>-5-methyl-4-hexen-1-ol
  参考文献：
  名称：

  Total synthesis of the meso-triterpene polyether teurilene

  摘要：

  The first total synthesis of the triterpene ether teurilene (1) has been accomplished utilizing two vanadium(V)-catalyzed oxidation-cyclization reactions with different stereoselectivities. The synthesis involved stereoselective and step-by-step construction of 2,5-cis- and 2,5-trans-tetrahydrofuran rings, vanadium(V)-catalyzed oxidation of 4-substituted 4-en-1-ol 40 and subsequent cyclization of the resulting anti-epoxy alcohol 41, and a similar oxidation-cyclization of 5-substituted 4-en-1-ol 49 by way of syn-epoxy alcohol 50. This was followed by construction of a third tetrahydrofuran ring by more conventional means. An improved synthesis of 1, which featured direct formation of bis(tetrahydrofuran) 51 from squalene derivative 66 by simultaneous double oxidation-cyclization, was also accomplished.

  DOI：

  10.1021/jo00007a013

文献信息

• Improved Procedure for the Synthesis of <i>gem-</i>Diiodoalkanes by the Alkylation of Diiodomethane. Scope and Limitations
  作者：James A. Bull、André B. Charette

  DOI：10.1021/jo8014616

  日期：2008.10.17

  employing a convenient modified procedure for the alkylation of NaCHI2 with alkyl iodides. Complete conversion to the diiodide is reliably obtained, avoiding a problematic separation of any remaining iodide starting material. Functional group tolerance toward olefins, acetals, ethers and silyl ethers, carbamates, and hindered esters is demonstrated. The use of an excess of LiCHI2 allows complete conversion

  通过采用方便的改良方法将NaCHI2与烷基碘烷基化，可以得到高至极好的收率的功能化的宝石二碘代烷烃。可靠地实现了向二碘化物的完全转化，避免了任何残留的碘化物原料的分离问题。证明了对烯烃，缩醛，醚和甲硅烷基醚，氨基甲酸酯和受阻酯的官能团耐受性。使用过量的LiCHI 2可以使烯丙基和苄基溴完全转化，而从二碘化物产物中消除得最少。
• HASHIMOTO, MASARU;HARIGAYA, HIROKO;YANAGIYA, MITSUTOSHI;SHIRAHAMA, HARUHI+, J. ORG. CHEM., 56,(1991) N, C. 2299-2311
  作者：HASHIMOTO, MASARU、HARIGAYA, HIROKO、YANAGIYA, MITSUTOSHI、SHIRAHAMA, HARUHI+

  DOI：——

  日期：——
• Total synthesis of the meso-triterpene polyether teurilene
  作者：Masaru Hashimoto、Hiroko Harigaya、Mitsutoshi Yanagiya、Haruhisa Shirahama

  DOI：10.1021/jo00007a013

  日期：1991.3

  The first total synthesis of the triterpene ether teurilene (1) has been accomplished utilizing two vanadium(V)-catalyzed oxidation-cyclization reactions with different stereoselectivities. The synthesis involved stereoselective and step-by-step construction of 2,5-cis- and 2,5-trans-tetrahydrofuran rings, vanadium(V)-catalyzed oxidation of 4-substituted 4-en-1-ol 40 and subsequent cyclization of the resulting anti-epoxy alcohol 41, and a similar oxidation-cyclization of 5-substituted 4-en-1-ol 49 by way of syn-epoxy alcohol 50. This was followed by construction of a third tetrahydrofuran ring by more conventional means. An improved synthesis of 1, which featured direct formation of bis(tetrahydrofuran) 51 from squalene derivative 66 by simultaneous double oxidation-cyclization, was also accomplished.