1-phenylhex-5-ene-1,3-diol | 140854-62-2

• 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: 1-phenylhex-5-ene-1,3-diol
• 英文别名: (1R,3R)-1-phenylhex-5-ene-1,3-diol
• CAS: 140854-62-2
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: XIBFDHGRGQMQBU-VXGBXAGGSA-N

物化性质

• 沸点：
  345.0±42.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  alpha-乙烯基苄基乙酸酯 、 1-phenylhex-5-ene-1,3-diol 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以34%的产率得到(E)-5,7-dihydroxy-1,7-diphenylhept-2-en-1-yl acetate
  参考文献：
  名称：

  Iron-Catalyzed Synthesis of C2 Aryl- and N-Heteroaryl-Substituted Tetrahydropyrans

  摘要：

  An iron-catalyzed cyclization of hydroxy allylic derivatives into tetrahydropyrans possessing an N-heteroaryl at C2 is disclosed. The reaction proceeds with good yield and in high diastereoselectivity in favor of the more stable isomer. The diastereoselectivity results from an iron-induced reopening of the tetrahydropyrans, allowing a thermodynamic equilibration. The method allows access to a variety of 2,6-disubstituted as well as 2,4,6-trisubstituted tetrahydropyrans that could be considered as attractive scaffolds for the pharmaceutical industry.

  DOI：

  10.1021/acs.joc.5b02371
• 作为产物：
  描述：

  (R)-1-Phenylbut-3-en-1-ol 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 caesium carbonate 、 臭氧 、 4-氯-3-硝基苯甲酸 、 (S)-(-)-5,5-二氯-6,6-二甲氧基-2,2-双(二苯基磷酸)-1,1-联苯基 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 40.25h， 生成 1-phenylhex-5-ene-1,3-diol
  参考文献：
  名称：

  手性 1,3-二醇连续亲核和亲电烯丙基化的催化剂定向非对映选择性和位点选择性：取代吡喃的无保护基合成

  摘要：

  通过手性 1,3-二醇的连续亲核和亲电烯丙基化，铱催化的无保护基合成 4-羟基-2,6-顺式或反式-吡喃保护基团、预金属化试剂或离散的醇-醛氧化还原反应。

  DOI：

  10.1002/chem.201404065

文献信息

• Aromatic aldehyde-selective aldol addition with aldehyde-derived silyl enol ethers
  作者：Takahiro Kawajiri、Reiya Ohta、Hiromichi Fujioka、Hironao Sajiki、Yoshinari Sawama

  DOI：10.1039/c7cc08936h

  日期：——

  enolates as nucleophiles with aromatic aldehydes chemoselectively proceeded in the presence of silyl triflate and 2,2′-bipyridyl to produce β-siloxy aldehydes, while the aliphatic aldehydes were completely recovered. The unprecedented chemoselectivities depend on the reactivities of the pyridinium-type intermediates derived from the aromatic and aliphatic aldehydes.

  在三氟甲硅烷基甲硅烷基酯和2,2'-联吡啶基存在下，使用醛衍生的甲硅烷基烯醇酸酯作为亲核试剂与芳香族醛进行的醛醇缩合反应进行化学选择性生成β-甲硅烷氧基醛，而脂肪族醛则被完全回收。前所未有的化学选择性取决于衍生自芳族和脂族醛的吡啶鎓类中间体的反应性。
• Gold-catalyzed cycloisomerizations of ene-ynamides
  作者：Sylvain Couty、Christophe Meyer、Janine Cossy

  DOI：10.1016/j.tet.2008.10.108

  日期：2009.2

  The gold-catalyzed cycloisomerizations of 1,6-ene-ynamides proceed under mild conditions and lead to cyclobutanones from terminal or trimethylsilyl substituted ynamides, or to carbonyl compounds bearing a 2,3-methanopyrrolidine subunit from substrates possessing a propargylic alcohol moiety. High diastereoselectivities are observed with 1,6-ene-ynamides having a stereocenter at the α or β position

  1，6-烯-酰胺的金催化的环异构化在温和的条件下进行，并从末端或三甲基甲硅烷基取代的酰胺中产生环丁酮，或从具有炔丙醇部分的底物上产生带有2,3-甲基吡咯烷亚基的羰基化合物。用在氮原子的α或β位置具有立体中心的1，6-烯-酰胺具有高的非对映选择性。
• Tetrahydropyran synthesis by palladium(II)-catalysed hydroxycarbonylation of hexenols: synthesis of (±)-diospongin A and (+)-civet cat compound
  作者：Ol'ga Karlubíková、Matej Babjak、Tibor Gracza

  DOI：10.1016/j.tet.2011.04.045

  日期：2011.7

  domino Pd-cyclisation/carbonylation/hydroxylation of (2S)-hept-6-en-2-ol 15 and O-TBDPS protected 1-phenylhex-5-en-1,3-diol 12, respectively, was used as a key step in the total syntheses of two natural products, civet cat (+)-2-[(2S,6S)-(6-methyltetrahydro-2H-pyran-2-yl)] acetic acid 1 and diospongin A 2. Moreover, an efficient synthesis of 2 using a multi Pd-cyclisation/carbonylation/cross-coupling transformation

  基于钯（II）催化己烯醇的分子内羟羰基化，已经开发了2,6-顺-四氢吡喃基乙酸的非对映选择性合成。（2S）-hept-6-en-2-ol 15和O -TBDPS保护的1-phenylhex-5-en-1,3-diol 12的多米诺Pd环化/羰基化/羟基化分别用作灵猫（+）-2-[（2 S，6 S）-（6-甲基四氢-2 H-吡喃-2-基）]乙酸1和双皂苷A两种天然产物的总合成中的关键步骤2。而且，有效合成2 使用多Pd环化/羰基化/交叉偶联转化已经实现。
• A Facile and Efficient Synthesis of 4-Hydroxy-2,6-<i>cis</i>-tetrahydropyrans via Tandem Cross-Metathesis/Thermal S_N2′ Reaction: Protecting-Group-Free Synthesis of (±)-Diospongin A
  作者：Kiyoun Lee、Hyoungsu Kim、Jiyong Hong

  DOI：10.1021/ol902125d

  日期：2009.11.19

  The tandem cross-metathesis/thermal SN2′ reaction was explored for the facile and efficient synthesis of 4-hydroxy-2,6-cis-tetrahydropyrans. The mildness of the thermal conditions allowed for the synthesis of 4-hydroxy-2,6-cis-tetrahydropyrans from base-sensitive substrates without the use of protecting groups. The tandem reaction enabled a protecting-group-free synthesis of (±)-diospongin A.

  探索了串联交叉复分解/热S N 2'反应的快速有效合成4-羟基-2,6-顺-四氢吡喃。热条件的温和性允许在不使用保护基的情况下从碱敏感的底物合成4-羟基-2，6-顺-四氢吡喃。串联反应使（±）-双倍体皂苷A的无保护基合成成为可能。
• Hoffmann, Rolf; Brueckner, Reinhard, Chemische Berichte, 1992, vol. 125, # 6, p. 1471 - 1484
  作者：Hoffmann, Rolf、Brueckner, Reinhard

  DOI：——

  日期：——