3-环己基丙-2-烯酸 | 673456-32-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 3-环己基丙-2-烯酸
• 英文名称: (Z)-3-cyclohexylpropenoic acid
• 英文别名: (Z)-3-cyclohexylacrylic acid；(Z)-3-cyclohexylprop-2-enoic acid
• CAS: 673456-32-1
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: GYEYFOYXHNRMGO-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  3-环己基丙-2-烯酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 26.0h， 生成 (E)-S-2-acetamidoethyl 3-cyclohexylprop-2-enethioate
  参考文献：
  名称：

  Modular Polyketide Synthases and cis Double Bond Formation:  Establishment of Activated cis-3-Cyclohexylpropenoic Acid as the Diketide Intermediate in Phoslactomycin Biosynthesis

  摘要：

  The majority of modular polyketide synthase (PKS) systems which generate unsaturated products do so with trans double bonds. Phoslactomycin B (PLM B) presents a class of antitumor and antiviral natural polyketide products that have unique structural features, including a linear unsaturated backbone with one trans and three cis double bonds. There is substantial evidence that trans double bonds are established by ketoreductase-dehydratase (KR-DH) didomains within a PKS module. In cases where modules containing these didomains appear to generate product containing a cis double bond, there is no experimental evidence to determine if they do so directly or if they also form a trans double bond with a subsequent isomerization step. A critical step in addressing this issue is establishing the stereochemistry of the polyketide intermediate which passes to the subsequent module. Herein, we demonstrate through a series of experiments that an activated cis-3-cyclohexylpropenoic acid is the diketide intermediate which passes from module 1 to module 2 of the PLM PKS. The trans isomer of the diketide intermediate could not be processed directly into PLM B by module 2 but could be converted to PLM B by degradation to cyclohexanecarboxylic acid and elongation by the entire PLM PKS. These observations indicate not only that module 1 with a DH-KR didomain is responsible for establishing the C-14-C-15 cis double bond of PLM B but also that the subsequent modules of the PKS clearly discriminate between the cis- and trans-diketide intermediate and do not contain domains capable of catalyzing double bond isomerization.

  DOI：

  10.1021/ja068818t
• 作为产物：
  描述：

  环己基乙炔 在 Lindlar's catalyst 喹啉 、 正丁基锂 、 氢气 作用下， 以 乙醚 、 乙醇 、 正己烷 为溶剂， 反应 5.0h， 生成 3-环己基丙-2-烯酸
  参考文献：
  名称：

  Modular Polyketide Synthases and cis Double Bond Formation:  Establishment of Activated cis-3-Cyclohexylpropenoic Acid as the Diketide Intermediate in Phoslactomycin Biosynthesis

  摘要：

  The majority of modular polyketide synthase (PKS) systems which generate unsaturated products do so with trans double bonds. Phoslactomycin B (PLM B) presents a class of antitumor and antiviral natural polyketide products that have unique structural features, including a linear unsaturated backbone with one trans and three cis double bonds. There is substantial evidence that trans double bonds are established by ketoreductase-dehydratase (KR-DH) didomains within a PKS module. In cases where modules containing these didomains appear to generate product containing a cis double bond, there is no experimental evidence to determine if they do so directly or if they also form a trans double bond with a subsequent isomerization step. A critical step in addressing this issue is establishing the stereochemistry of the polyketide intermediate which passes to the subsequent module. Herein, we demonstrate through a series of experiments that an activated cis-3-cyclohexylpropenoic acid is the diketide intermediate which passes from module 1 to module 2 of the PLM PKS. The trans isomer of the diketide intermediate could not be processed directly into PLM B by module 2 but could be converted to PLM B by degradation to cyclohexanecarboxylic acid and elongation by the entire PLM PKS. These observations indicate not only that module 1 with a DH-KR didomain is responsible for establishing the C-14-C-15 cis double bond of PLM B but also that the subsequent modules of the PKS clearly discriminate between the cis- and trans-diketide intermediate and do not contain domains capable of catalyzing double bond isomerization.

  DOI：

  10.1021/ja068818t

文献信息

• Influence of the Double-Bond Geometry of the Michael Acceptor on Copper-Catalyzed Asymmetric Conjugate Addition
  作者：Magali Vuagnoux-d'Augustin、Alexandre Alexakis

  DOI：10.1002/ejoc.200700424

  日期：2007.12

  aspects, a study of the influence of the (E)/(Z) double-bond geometry of the Michael acceptor on the enantioselectivity of copper-catalyzed asymmetric conjugate addition reactions has been realized. In spite of numerous articles concerning copper-catalyzed asymmetric conjugate addition reactions, the major factors of such a reaction are quite difficult to elucidate. Although our experiments have not allowed

  着眼于机理方面，研究了迈克尔受体的 (E)/(Z) 双键几何结构对铜催化不对称共轭加成反应的对映选择性的影响。尽管有许多关于铜催化不对称共轭加成反应的文章，但很难阐明这种反应的主要因素。虽然我们的实验不允许我们定义严格的规则，但他们强调了一些在考虑铜试剂形成双键时不可忽视的因素，例如 (E)/(Z) 异构化和空间方面，这可能会导致改变底物的反应构象。电子效应还可以改变双键的极化并影响亲核攻击。
• Semireduction of alkynoic acids via a transition metal-free α borylation-protodeborylation sequence
  作者：Astha Verma、R. Justin Grams、Brett P. Rastatter、Webster L. Santos

  DOI：10.1016/j.tet.2019.02.030

  日期：2019.4

  A method for the semi-reduction of alkynoic acids through an α-borylation and subsequent protodeborylation mechanism has been developed. The transition metal-free protocol is achieved through the activation of bis(pinacolato)diboron by an in situ generated carboxylate moiety yielding aryl acrylic acids. Our studies demonstrate an unprecedented dual role for the carboxylate anion that involves the activation

  已经开发了一种通过α-硼化和随后的原脱硼机理半还原炔酸的方法。不含过渡金属的方案是通过原位产生的羧酸酯部分活化双（频哪醇）二硼来生成的，从而生成芳基丙烯酸。我们的研究表明，羧酸根阴离子具有前所未有的双重作用，它涉及二硼试剂的活化以及在α-硼化反应中的直接作用。
• The photomediated reaction of alkynes with cycloalkanes
  作者：Roísín A. Doohan、John J. Hannan、Niall W. A. Geraghty

  DOI：10.1039/b517631j

  日期：——

  of a photomediator such as benzophenone, alkynes with electron-withdrawing groups react with cycloalkanes to give vinyl cycloalkanes. The reaction involves the regiospecific addition of a photochemically generated cycloalkyl radical to the beta-carbon of the alkyne. The stereochemical outcome of the reaction depends on the nature of the photomediator and alkyne used.

  在光介体如二苯甲酮的存在下，具有吸电子基团的炔烃与环烷烃反应生成乙烯基环烷烃。该反应涉及将光化学产生的环烷基的区域特异性加成到炔烃的β-碳上。反应的立体化学结果取决于所使用的光介体和炔烃的性质。
• NEW METHOD OF SYNTHESIS OF CHITOSAN DERIVATIVES AND USES THEREOF
  申请人：Bosti Trading Ltd.

  公开号：EP3865535A1

  公开（公告）日：2021-08-18

  The present invention is directed to a new cross-linked chitosan, preparations, compositions and uses thereof. In particular, the invention relates to nanoparticles and compositions thereof useful as active agents and delivery systems for at least one bioactive agent.

  本发明涉及一种新的交联壳聚糖及其制剂、组合物和用途。特别是，本发明涉及可用作活性剂和至少一种生物活性剂输送系统的纳米颗粒及其组合物。
• Key structural features of cis-cinnamic acid as an allelochemical
  作者：Masato Abe、Keisuke Nishikawa、Hiroshi Fukuda、Kazunari Nakanishi、Yuta Tazawa、Tomoya Taniguchi、So-young Park、Syuntaro Hiradate、Yoshiharu Fujii、Katsuhiro Okuda、Mitsuru Shindo

  DOI：10.1016/j.phytochem.2012.08.001

  日期：2012.12

  1-O-cis-cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals isolated from Spiraea thunbergii Sieb. It is suggested that it derives its strong inhibitory activity from cis-cinnamic acid, which is crucial for phytotoxicity. It was synthesized to confirm its structure and bioactivity, and also a series of cis-cinnamic acid analogues were prepared to elucidate the key features of cis-cinnamic acid for lettuce root growth inhibition. The cis-cyclopropyl analogue showed potent inhibitory activity while the saturated and alkyne analogues proved to be inactive, demonstrating the importance of the as-double bond. Moreover, the aromatic ring could not be replaced with a saturated ring. However, the 1,3-dienylcyclo-hexene analogue showed strong activity. These results suggest that the geometry of the C-C double bond between the carboxyl group and the aromatic ring is essential for potent inhibitory activity. In addition, using several light sources, the photostability of the cinnamic acid derivatives and the role of the C-C double bond were also investigated. (c) 2012 Elsevier Ltd. All rights reserved.