(+/-)-methyl 8-hydroxy-5,6-octadienoate | 38818-76-7

• 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: (+/-)-methyl 8-hydroxy-5,6-octadienoate
• 英文别名: methyl 8-hydroxy-5,6-octadienoate；Methyl-8-hydroxy-5,6-octadienoat
• CAS: 38818-76-7
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: ISPVMFAFUVDHKP-UHFFFAOYSA-N

物化性质

• 沸点：
  269.2±30.0 °C(Predicted)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-methyl 8-hydroxy-5,6-octadienoate 、 (1R,2R)-(+)-N,N-二甲基-1,2-双[3-(三氟醚甲基)苯-1,2-乙烷二胺 在 N,N-二乙基苯胺 、 三氯化磷 作用下， 生成
  参考文献：
  名称：

  Chiral Diamines for a New Protocol To Determine the Enantiomeric Composition of Alcohols, Thiols, and Amines by 31P, 1H, 13C, and 19F NMR

  摘要：

  A new experimental protocol is described which greatly improves our recently reported method for the determination of the enantiomeric composition of alcohols, phenols, thiols, and amines. Thus, successive addition into the NMR tube of (1) a chiral fluorinated diamine (or any other chiral C-2 symmetrical diamine), (2) CDCl3, (3) a tertiary amine, (4) PCl3, and 5) the chiral alcohol, phenol, thiol, or amine allows a P-31 NMR spectrum of the diastereomeric derivatives to be recorded in 5 min. The method is accurate and very general, and no kinetic discrimination is observed. Sulfuration or selenation of the trivalent phosphorus derivatives, carried out in the NMR tube, allows for a second P-31 NMR determination, in addition to the H-1, C-13, and F-19 NMR spectra which may also be recorded.

  DOI：

  10.1021/jo00091a019
• 作为产物：
  描述：

  (E)-methyl 7-oxo-hept-5-enoate 在 吡啶 、 三乙胺 、 乙烯基乙醚 、 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 12.25h， 生成 (+/-)-methyl 8-hydroxy-5,6-octadienoate
  参考文献：
  名称：

  A short synthesis of the antifungal principle of Sapium japonicum

  摘要：

  Methyl 8-hydroxy-5,6-octadienoate (1), the antifungal principle of Sapium japonicum, was prepared via the oxidation and [2,3] sigmatropic rearrangement of a dienyl selenide precursor.

  DOI：

  10.1016/s0040-4039(00)61269-8

文献信息

• Dimethylaluminum halide induced reactions of formaldehyde with alkynes. Synthesis of α-allenic alcohols and Z-3-chloroallylic alcohols
  作者：David J. Rodini、Barry B. Snider

  DOI：10.1016/0040-4039(80)80199-7

  日期：1980.1

  The CH2O·Me2AlCl complex reacts with terminal alkynes to give α-allenic alcohols via a formal ene reaction and Z-3-chloroallylic alcohols via a stereospecifically syn Friedel-Crafts addition.

  CH 2 O·Me 2 AlCl配合物与末端炔烃反应，通过形式烯反应生成α-烯醇，Z --3-氯代烯丙基醇通过立体特异性合成Friedel-Crafts加成反应。
• [3,3]sigmatropic ring expansion of cyclic thionocarbonates. 13.1 synthesis of medium-membered heterocyclic allenes and synthetic application to antifungal constitutent of Sapium japonicum
  作者：Shinya Harusawa、Hideki Moriyama、Naoki Kase、Hirofumi Ohishi、Ryuji Yoneda、Takushi Kurihara

  DOI：10.1016/0040-4020(95)00306-s

  日期：1995.6

  thionocarbonates (2i-k) afforded a new type of strained 8-membered heterocyclic allenes (3i-k) in high yields. The MNDO optimized structure of 3i indicated the allenyl moiety was bent and strained. The reactivity of 8-membered cyclic allenes was also examined. Further, using this methodology with a novel application of a SmI2-HMPA reduction of the resulting heterocyclic allene (3n), an antifungal constituent

  通过炔基环状硫代碳酸酯（2）的[3，3]σ重排，合成了包含在8至11元环范围内的SCOO部分的环状烯（3a-k，3n）。六元环状硫代碳酸酯（2i-k）的扩环以高收率提供了一种新型的应变八元杂环丙二烯（3i-k）。MNDO的3i优化结构表明该烯基部分弯曲和拉紧。还检查了8元环烯的反应性。此外，将该方法与SmI 2 -HMPA的新颖应用一起使用，可减少所得杂环亚丙基（3n），合成了刺五加的抗真菌成分，（±）-8-羟基-5,6-辛二烯酸甲酯（24）。
• RODIUI D. J.; SNIDER B. B., TETRAHEDRON, 1980, 21, NO 40, 3857-3860
  作者：RODIUI D. J.、 SNIDER B. B.

  DOI：——

  日期：——
• HUGUET, JOAN;REYES, MARIA DEL CARMEN, TETRAHEDRON LETT., 31,(1990) N0, C. 4279-4280
  作者：HUGUET, JOAN、REYES, MARIA DEL CARMEN

  DOI：——

  日期：——
• GOODING, OWEN W.;BEARD, COLIN C.;JACKSON, DAVID Y.;WREN, DOUGLAS L.;COOPE+, J. ORG. CHEM., 56,(1991) N, C. 1083-1088
  作者：GOODING, OWEN W.、BEARD, COLIN C.、JACKSON, DAVID Y.、WREN, DOUGLAS L.、COOPE+

  DOI：——

  日期：——