(E)-3-hydroxy-5-phenylpent-4-enoic acid | 61752-38-3

• 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-5-phenylpent-4-enoic acid
• 英文别名: 3-Hydroxy-5-phenylpent-4-enoic acid
• CAS: 61752-38-3
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: JKDYSKHGCXBPQC-VOTSOKGWSA-N

物化性质

• 熔点：
  88-93 °C
• 沸点：
  426.6±45.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-hydroxy-5-phenylpent-4-enoic acid 在 N,N-二甲基甲酰胺二甲基缩醛 作用下， 以 氯仿 为溶剂， 以70%的产率得到1-苯-1,3-丁二烯
  参考文献：
  名称：

  Mulzer, Johann; Bruentrup, Gisela; Kuehl, Uwe, Chemische Berichte, 1982, vol. 115, # 11, p. 3453 - 3469

  摘要：

  DOI：
• 作为产物：
  描述：

  tert-butyl (4E)-3-hydroxy-5-phenyl-4-pentenoate 生成 (E)-3-hydroxy-5-phenylpent-4-enoic acid
  参考文献：
  名称：

  DUTHALER, RUDOLF O.;HEROLD, PETER;LOTTENBACH, WILLY;OERTLE, KONRAD;RIEDIK+, ANGEW. CHEM., 101,(1989) N, C. 490-491

  摘要：

  DOI：

文献信息

• Synthesis of Weinreb amides using diboronic acid anhydride-catalyzed dehydrative amidation of carboxylic acids
  作者：Naoyuki Shimada、Naoya Takahashi、Naoki Ohse、Masayoshi Koshizuka、Kazuishi Makino

  DOI：10.1039/d0cc05630h

  日期：——

  The first successful example of the direct synthesis of Weinreb amides using catalytic hydroxy-directed dehydrative amidation of carboxylic acids using the diboronic acid anhydride catalyst is described. The methodology is applicable to the concise syntheses of eight α-hydroxyketone natural products, namely, sattabacin, 4-hydroxy sattabacin, kurasoins A and B, soraphinols A and B, and circumcins B

  描述了使用二硼酸酐酸酐催化剂使用羧酸的催化羟基直接脱水酰胺化直接合成Weinreb酰胺的第一个成功实例。该方法适用于八种α-羟基酮天然产物的简明合成，它们分别为司塔巴星，4-羟基司他巴星，库拉索菌素A和B，茄型酚A和B以及环丁香素B和C。
• Acetic Acid Aldol Reactions in the Presence of Trimethylsilyl Trifluoromethanesulfonate
  作者：C. Wade Downey、Miles W. Johnson、Daniel H. Lawrence、Alan S. Fleisher、Kathryn J. Tracy

  DOI：10.1021/jo100828c

  日期：2010.8.6

  TMSOTf and a trialkylamine base, acetic acid undergoes aldol addition to non-enolizable aldehydes under exceptionally mild conditions. Acidic workup yields the β-hydroxy carboxylic acid. The reaction appears to proceed via a three-step, one-pot process, including in situ trimethylsilyl ester formation, bis-silyl ketene acetal formation, and TMSOTf-catalyzed Mukaiyama aldol addition. Independently synthesized

  在TMSOTf和三烷基胺碱的存在下，乙酸在异常温和的条件下会发生醛醇加成到不可烯化的醛中的现象。酸性后处理产生β-羟基羧酸。该反应似乎通过三步一锅法进行，包括原位形成三甲基甲硅烷基酯，形成双甲硅烷基烯酮缩醛和TMSOTf催化的Mukaiyama醛醇缩合。独立合成的TMSOAc在相似条件下也经历了羟醛加成反应。
• Studies on the stereoselective selenolactonization, hydroxy and methoxy selenenylation of α- and β-hydroxy acids and esters. Synthesis of δ- and γ-lactones
  作者：Carmela Aprile、Michelangelo Gruttadauria、Maria E Amato、Francesca D'Anna、Paolo Lo Meo、Serena Riela、Renato Noto

  DOI：10.1016/s0040-4020(03)00206-0

  日期：2003.3

  The diastereoselective synthesis of hydroxy substituted γ- and δ-lactones was accomplished following two approaches. A 5- or 6-endo cyclization promoted by electrophilic selenium reagents of α- or β-hydroxy acids and a 5- or 6-exo cyclization of hydroxy esters obtained through a diastereoselective hydroxy selenenylation reaction of α- or β-hydroxy esters. Moreover, the diastereoselective methoxy selenenylation

  羟基取代的γ-和δ-内酯的非对映选择性合成是通过两种方法完成的。的5-或6-内环化促进由α-或β羟基酸电硒试剂和一个5-或6-外通过α-或β-羟基酯的非对映选择性羟基硒烯化反应获得的羟基酯的环化。另外，对上述化合物的非对映选择性的甲氧基亚硒基化进行了研究，结果表明在羟基亚硒基化条件下不反应的化合物在甲氧基亚硒基化条件下产生了脱保护的二醇。通过制备不对称官能化的对称化合物证明了甲氧基亚硒基化方法的有用性。发现产率和选择性取决于取代基（经历亲核攻击的碳原子上的Ph或烷基），环化方式，动力学或热力学控制条件。在后一种情况下，硅胶起着重要作用。
• SYNTHETIC METHODS AND COMPOUNDS RELATED THERETO
  申请人：University Of Alaska Fairbanks

  公开号：US20150184206A1

  公开（公告）日：2015-07-02

  Disclosed herein are synthetic methods and compounds related to the compounds that are useful as or in the production of biologically active compounds. Stereoselective and stereospecific synthetic methods are disclosed to produce compounds, such as, for example, γ,δ-unsaturated-β-hydroxyesters and aminated derivatives thereof, at high yields with desired stereochemistry. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  本文公开了与合成生物活性化合物有关的合成方法和化合物。公开了立体选择性和立体特异性合成方法，以高收率和所需立体化学合成化合物，例如γ，δ-不饱和-β-羟基酯及其氨基衍生物。本摘要旨在作为特定领域搜索的扫描工具，并不意味着限制本发明。
• Stereocontrolled approach to δ- and γ-lactones and 1,3-diols. The role of X− ion in the selenolactonization
  作者：Michelangelo Gruttadauria、Carmela Aprile、Renato Noto

  DOI：10.1016/s0040-4039(02)00093-x

  日期：2002.2

  Two complementary approaches have been realized for the stereoselective synthesis of 4,6-disubstituted δ-lactones and 1,3-anti and syn diols. In the 6-endo selenolactonization the role of the X− ion on the stereoselectivity is shown. Moreover, the highly stereoselective transformation of the 6-endo δ-lactone to the 5-exo γ-lactone is reported.

  对于4，6-二取代的δ-内酯与1，3-抗和合成二醇的立体选择性合成，已经实现了两种互补的方法。在6-内切selenolactonization的X的作用-显示在立体选择性离子。此外，6-的高度立体选择性转化内切δ内酯到5-外型报道γ内酯。