(E)-3-Hydroxy-1-phenyl-4-vinyl-1,5-hexadiene | 159854-35-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-3-Hydroxy-1-phenyl-4-vinyl-1,5-hexadiene
• 英文别名: (E)-6-phenyl-3-vinylhex-1,5-dien-4-ol；(1E)-4-ethenyl-1-phenylhexa-1,5-dien-3-ol
• CAS: 159854-35-0；365515-58-8
• 化学式: C₁₄H₁₆O
• 分子量: 200.28
• InChiKey: NBQVCYOMTGKQQX-ZHACJKMWSA-N

物化性质

• 沸点：
  333.517±31.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  0.994±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 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)-3-Hydroxy-1-phenyl-4-vinyl-1,5-hexadiene 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以62%的产率得到(E)-3-Phenyl-octa-5,7-dienal
  参考文献：
  名称：

  铟介导的共轭醛的γ-戊二烯基化：通过氧化-Cope-环加成反应制得的氢化茚的合成子

  摘要：

  将戊二烯基铟加成到不饱和醛上，由1，2-加成得到被1，4-二烯单元取代的醇7。随后的阴离子氧基-Cope重排提供了迈克尔1，4-加成产物8。Wittig反应，然后进行分子内[2 + 4]环加成，以对映选择性的方式提供了氢化茚骨架（五个步骤）。

  DOI：

  10.1016/s0040-4039(99)01540-3
• 作为产物：
  描述：

  反式肉桂醛 、 (E)-5-bromopenta-1,3-diene 在 indium 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到(E)-3-Hydroxy-1-phenyl-4-vinyl-1,5-hexadiene
  参考文献：
  名称：

  铟介导的共轭醛的γ-戊二烯基化：通过氧化-Cope-环加成反应制得的氢化茚的合成子

  摘要：

  将戊二烯基铟加成到不饱和醛上，由1，2-加成得到被1，4-二烯单元取代的醇7。随后的阴离子氧基-Cope重排提供了迈克尔1，4-加成产物8。Wittig反应，然后进行分子内[2 + 4]环加成，以对映选择性的方式提供了氢化茚骨架（五个步骤）。

  DOI：

  10.1016/s0040-4039(99)01540-3

文献信息

• A highly efficient and practical preparation of 2,4-pentadienyltitaniums and their γ-selective addition reaction with aldehydes and ketones
  作者：Sentaro Okamoto、Fumie Sato

  DOI：10.1016/s0022-328x(00)00911-6

  日期：2001.4

  were readily prepared from a divalent titanium reagent, Ti(O–i-Pr)4/2i-PrMgCl, and penta-1,4-dien-3-ol or penta-2,4-dien-1-ol derivatives, and the organotitaniums thus prepared reacted with aldehydes and ketones smoothly to afford the corresponding penta-1,4-dien-3-yl carbinols highly predominantly in excellent yield.

  被容易地从二价钛试剂制备的各种戊-2,4- dienyltitanium复合物，包括那些具有一个官能团的，钛（O-我-Pr）4 /2我-PrMgCl，和五-1,4- dien- 3-ol或五-2,4-二烯-1-醇衍生物以及如此制得的有机钛与醛和酮平稳反应，从而以优异的收率非常主要地提供相应的五-1,4-二烯-3-基甲醇。
• Facile and Highly Stereoselective Synthesis of Homoallylic Alcohols Using Organosilicon Intermediates
  作者：Shu Kobayashi、Koichi Nishio

  DOI：10.1021/jo00101a021

  日期：1994.11

  Allyltrichlorosilanes regioselectively reacted with aldehydes in N,N-dimethylformamide (DMF) without a catalyst to afford the corresponding homoallylic alcohols in high yields. The reactions proceeded under neutral conditions, and syn- and anti-homoallylic alcohols were stereoselectively obtained from (Z)- and (E)-allyltrichlorosilanes, respectively. In these reactions, DMF coordinated to the silicon atom of the allyltrichlorosilanes to form hypervalent silicates, which in turn reacted with aldehydes smoothly. Solvent effects in these reactions were also examined. The reactions were applied to the one-pot synthesis of homoallylic alcohols from allylic chlorides via organosilicon intermediates. While syn-homoallylic alcohols were prepared from (Z)-allyl chlorides, antihomoallylic alcohols were obtained from (E)-allyl chlorides. Unique regioselectivities in the reactions of 1-chloro-2,4-pentadiene were also found. Finally, the one-pot synthesis of homoallylic alcohols from 1,3-dienes is reported.
• Indium-Mediated γ-Pentadienylation of Aldehydes and Ketones:  Cross-Conjugated Trienes for Diene-Transmissive Cycloadditions
  作者：Simon Woo、Neil Squires、Alex G. Fallis

  DOI：10.1021/ol990695c

  日期：1999.8.1

  [GRAPHICS]Treatment of 5-bromo-1,3-pentadiene with indium metal in the presence of carbonyl compounds results in gamma-pentadienylation to generate the 1,4-diene. Elimination of the resulting alcohol affords cross conjugated triene systems which rapidly react with appropriate dienophiles to give tandem intermolecular Diels-Alder adducts.
• Kobayashi Shue, Nishio Koichi, J. Org. Chem, 59 (1994) N 22, S 6620-6628
  作者：Kobayashi Shue, Nishio Koichi

  DOI：——

  日期：——
• Indium mediated γ-pentadienylation of conjugated aldehydes: synthons for hydrindanes by an oxy-Cope-cycloaddition strategy
  作者：Alex Melekhov、Alex G Fallis

  DOI：10.1016/s0040-4039(99)01540-3

  日期：1999.11

  of pentadienylindium to unsaturated aldehydes afforded the alcohols 7, from 1,2-addition, substituted with a 1,4-diene unit. Subsequent anionic oxy-Cope rearrangement provided the Michael 1,4-addition product 8. Wittig reaction followed by intramolecular [2+4] cycloaddition afforded the hydrindane skeleton in an enantioselective manner (five steps).

  将戊二烯基铟加成到不饱和醛上，由1，2-加成得到被1，4-二烯单元取代的醇7。随后的阴离子氧基-Cope重排提供了迈克尔1，4-加成产物8。Wittig反应，然后进行分子内[2 + 4]环加成，以对映选择性的方式提供了氢化茚骨架（五个步骤）。