4-Hydroxy-6-phenyl-3-vinyl-1-butene | 159854-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Hydroxy-6-phenyl-3-vinyl-1-butene
• 英文别名: 1-phenyl-4-vinyl-5-hexen-3-ol；4-Ethenyl-1-phenylhex-5-en-3-ol
• CAS: 159854-34-9；365515-59-9
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: NPQSXDWEEVGCPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  4-Hydroxy-6-phenyl-3-vinyl-1-butene 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 苯 为溶剂， 生成 4-Ethenylhexa-3,5-dienylbenzene
  参考文献：
  名称：

  Indium-Mediated γ-Pentadienylation of Aldehydes and Ketones:  Cross-Conjugated Trienes for Diene-Transmissive Cycloadditions

  摘要：

  [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.

  DOI：

  10.1021/ol990695c
• 作为产物：
  描述：

  苯丙醛 、 tributyl(2,4-pentadienyl)stannane 在 (R)-2,2'-bis(Ph₂P)-1,1'-binaphthyl*AgOTf 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以52%的产率得到4-Hydroxy-6-phenyl-3-vinyl-1-butene
  参考文献：
  名称：

  BINAP•Ag(I)配合物催化烯丙基锡烷与醛的不对称加成

  摘要：

  以BINAP•AgOTf配合物为催化剂实现了醛与烯丙基三烷基锡烷的催化不对称烯丙基化反应。通过在室温下在 THF 中搅拌 BINAP 和三氟甲磺酸银 (I) 的等摩尔混合物，很容易制备手性银 (I) 催化剂。各种芳香醛和 α,β-不饱和醛的烯丙基化产生了高产率和显着的对映选择性。γ-取代的烯丙基锡烷如2-丁烯基三丁基锡烷和三烷基-2,4-戊二烯基锡烷的加成专门得到γ-加合物。无论双键的构型如何，在与 2-丁烯基三丁基锡烷的反应中也获得了高抗选择性。

  DOI：

  10.1246/bcsj.74.1129

文献信息

• Asymmetric Addition of Allylsilanes to Aldehydes: A Cr/Photoredox Dual Catalytic Approach Complementing the Hosomi–Sakurai Reaction
  作者：Felix Schäfers、Subhabrata Dutta、Roman Kleinmans、Christian Mück-Lichtenfeld、Frank Glorius

  DOI：10.1021/acscatal.2c03960

  日期：2022.10.7

  The allylation of aldehydes is a fundamental transformation in synthetic organic chemistry. Among the multitude of available reagents, allylsilanes especially have been established as a preferred allyl source. As initially reported by Hosomi and Sakurai, these non-toxic and highly stable reagents add to carbonyls via an open transition state upon Lewis acid activation. Herein, we report a general strategy

  醛的烯丙基化是合成有机化学中的一个基本转变。在众多可用的试剂中，特别是烯丙基硅烷已被确立为优选的烯丙基源。正如 Hosomi 和 Sakurai 最初报道的那样，这些无毒且高度稳定的试剂在路易斯酸活化后通过开放过渡态添加到羰基中。在这里，我们报告了一种通用策略，通过切换到光催化活化结合封闭过渡态（铬催化），以与已建立的 Hosomi-Sakurai 条件相反的化学和非对映选择性获得各种有价值的高烯丙醇。而且，这种双重催化方法展示了一种引入优异水平对映选择性的直接方法，其温和的条件允许广泛的底物范围，包括手性硼取代产物作为亮点。为了强调合成效用，我们的方法被用作生物活性化合物合成和类固醇衍生物后期功能化的关键步骤。详细的机械研究和 DFT 计算暗示了前所未有的光引发链正在运行。
• 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.
• Kobayashi Shue, Nishio Koichi, J. Org. Chem, 59 (1994) N 22, S 6620-6628
  作者：Kobayashi Shue, Nishio Koichi

  DOI：——

  日期：——
• Asymmetric Addition of Allylic Stannanes to Aldehydes Catalyzed by BINAP•Ag(I) Complex
  作者：Akira Yanagisawa、Hiroshi Nakashima、Yoshinari Nakatsuka、Atsushi Ishiba、Hisashi Yamamoto

  DOI：10.1246/bcsj.74.1129

  日期：2001.6

  Catalytic asymmetric allylation of aldehydes with allylic trialkylstannanes was achieved with BINAP•AgOTf complex as catalyst. The chiral silver(I) catalyst was readily prepared by stirring an equimolar mixture of BINAP and silver(I) triflate in THF at room temperature. The allylation of a variety of aromatic and α,β-unsaturated aldehydes resulted in high yields and remarkable enantioselectivities

  以BINAP•AgOTf配合物为催化剂实现了醛与烯丙基三烷基锡烷的催化不对称烯丙基化反应。通过在室温下在 THF 中搅拌 BINAP 和三氟甲磺酸银 (I) 的等摩尔混合物，很容易制备手性银 (I) 催化剂。各种芳香醛和 α,β-不饱和醛的烯丙基化产生了高产率和显着的对映选择性。γ-取代的烯丙基锡烷如2-丁烯基三丁基锡烷和三烷基-2,4-戊二烯基锡烷的加成专门得到γ-加合物。无论双键的构型如何，在与 2-丁烯基三丁基锡烷的反应中也获得了高抗选择性。
• 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.