(S)-3-phenylhex-5-enoic acid | 127393-00-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (S)-3-phenylhex-5-enoic acid
• 英文别名: (3S)-3-phenylhex-5-enoic acid
• CAS: 127393-00-4
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: KARGDSIBBUXAAF-NSHDSACASA-N

物化性质

• 沸点：
  306.7±11.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-甲氧基苄醇 、 (S)-3-phenylhex-5-enoic acid 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以99%的产率得到4-methoxybenzyl (R)-(2-phenylpent-4-en-1-yl)carbamate
  参考文献：
  名称：

  Synthesis of a macrocycle based on Linked Amino Acid Mimetics (LAAM)

  摘要：

  We report the synthesis of a macrocycle utilizing a novel framework of standard amino acids in combination with subunits that we have named as Linked Amino Acid Mimetics (LAAMs). Macrocycles based on the LAAM concept provide both a peptide targeting region and two independently variable functional regions. In the prototype structure, the commonly known Arg-Gly-Asp (RGD) sequence was used for the targeting region. The functional regions contain a phenyl group, and the linkage was formed via a Ring-Closing Metathesis (RCM) reaction. (c) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2013.08.041
• 作为产物：
  描述：

  (4S)-4-phenyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one 在 lithium hydroxide monohydrate 、 双氧水 、 苯硫酚铜(I) 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 7.0h， 生成 (S)-3-phenylhex-5-enoic acid
  参考文献：
  名称：

  Synthesis of a macrocycle based on Linked Amino Acid Mimetics (LAAM)

  摘要：

  We report the synthesis of a macrocycle utilizing a novel framework of standard amino acids in combination with subunits that we have named as Linked Amino Acid Mimetics (LAAMs). Macrocycles based on the LAAM concept provide both a peptide targeting region and two independently variable functional regions. In the prototype structure, the commonly known Arg-Gly-Asp (RGD) sequence was used for the targeting region. The functional regions contain a phenyl group, and the linkage was formed via a Ring-Closing Metathesis (RCM) reaction. (c) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2013.08.041

文献信息

• Asymmetric Ni-Catalyzed Conjugate Allylation of Activated Enones
  作者：Joshua D. Sieber、James P. Morken

  DOI：10.1021/ja710922h

  日期：2008.4.1

  The nickel-catalyzed enantioselective addition of allylboronic acid pinacol ester, allylB(pin), is described. This reaction is highly effective with dialkylidene ketones and favors the allylation of the benzylidene site in nonsymmetric substrates. The reaction appears to proceed by conversion of the dialkylidene ketone substrate to an unsaturated pi-allyl complex (I), followed by reductive elimination

  描述了镍催化的烯丙基硼酸频哪醇酯烯丙基 B(pin) 的对映选择性加成。该反应对二亚烷基酮非常有效，并有利于非对称底物中亚苄基位点的烯丙基化。该反应似乎是通过将二亚烷基酮底物转化为不饱和的 pi-烯丙基络合物 (I)，然后进行还原消除来进行的。当使用手性配体 14 时，一系列底物的对映选择性范围为 91% 至 94% ee。
• Enantioselective Rhodium‐Catalyzed Allylic Alkylation of β,γ‐Unsaturated α‐Amino Nitriles: Synthetic Homoenolate Equivalents
  作者：Timothy B. Wright、Ben W. H. Turnbull、P. Andrew Evans

  DOI：10.1002/anie.201900442

  日期：2019.7.15

  An enantioselective rhodium‐catalyzed allylic alkylation of β,γ‐unsaturated α‐amino nitriles is described. This protocol provides a novel approach for the construction of β‐stereogenic carbonyl derivatives via the catalytic asymmetric alkylation of a homoenolate equivalent. The particularly challenging nature of this transformation is highlighted by the fact that three modes of selectivity must be

  描述了β，γ-不饱和α-氨基腈的对映体选择性铑催化的烯丙基烷基化反应。该方案为通过均烯酸酯等同物的催化不对称烷基化提供了一种构建β-立体异构羰基衍生物的新方法。这一转变特别具有挑战性，因为除了几何控制外，还必须操纵三种选择性模式，即区域选择性和对映选择性。γ-立体异构的氰基烯胺产品可以很容易地就地水解以提供β-取代的羧酸，从而可以方便地获得许多相关的羰基衍生物。另外，对照实验表明，手性铑烯丙基中间体可促进E的选择性形成。氰基烯胺产品，这一点至关重要，因为Z异构体的对映体控制量大大降低。
• Enantioenriched acid, ester, and ketone β-phenyl homoenolate synthetic equivalents from N-Boc-N-(p-methoxyphenyl)cinnamylamine
  作者：Marna C Whisler、Eric D Soli、Peter Beak

  DOI：10.1016/s0040-4039(00)01663-4

  日期：2000.12

  β-substituted ketones. Reaction of the lithiated intermediate with ketones affords oxazolidinones, which can be reductively ring-opened with DIBAL and hydrolyzed to provide enantioenriched β-substituted, α′-hydroxy ketones. These transformations demonstrate that the enantioselective lithiation of N-Boc-N-(p-methoxyphenyl)cinnamylamine provides a reactive intermediate which can be a ketone, acid, or ester

  通过3，3-二取代的烯甲酸酯的水解获得的β-取代的高度对映体富集的醛的氧化，得到了对映体富集的β-取代的酸和酯。富含对映体的3,3-二取代的烯甲酸酯的锂化以及随后与亲电试剂的反应提供了乙烯基取代的烯甲酸酯。使用苄基和烷基卤化物亲电试剂可得到α-取代的烯甲酸酯，可将其水解以提供对映体富集的β-取代的酮。锂化的中间体与酮反应得到恶唑烷酮，其可以用DIBAL还原性开环并水解以提供对映体富集的β-取代的α'-羟基酮。这些转化表明N -Boc- N-（p的对映选择性锂化-甲氧基苯基）肉桂胺提供了反应性中间体，该中间体可以是酮，酸或酯均烯酸酯合成子。