(Z)-3-(cyclohex-1-en-1-yl)acrylic Acid | 85437-89-4

• 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
• 英文名称: (Z)-3-(cyclohex-1-en-1-yl)acrylic Acid
• 英文别名: 3-(cyclohex-1-en-1-yl)acrylic acid；(Z)-3-(cyclohexen-1-yl)prop-2-enoic acid
• CAS: 85437-89-4
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: HTBJZZUJRAWYLX-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  (Z)-3-(cyclohex-1-en-1-yl)acrylic Acid 在 二苯基膦叠氮化物 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  异氰酸二烯酯的 6π-电环化合成取代的 2-吡啶酮

  摘要：

  已经开发了二烯基羧酸的一锅Curtius重排，然后是6π-电环化过程以形成取代的2-吡啶酮产物。由脂肪酸生成的异氰酸二烯酯比其芳族对应物更具反应性。此外，羧酸的取代模式对环化效率有影响。

  DOI：

  10.1021/acs.joc.2c00258
• 作为产物：
  描述：

  (Z)-3-(1-cyclohexen-1-yl)-2-propenoic acid ethyl ester 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以85%的产率得到(Z)-3-(cyclohex-1-en-1-yl)acrylic Acid
  参考文献：
  名称：

  Key structural features of cis-cinnamic acid as an allelochemical

  摘要：

  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.

  DOI：

  10.1016/j.phytochem.2012.08.001

文献信息

• 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。
• Vinly copper reagents-16. Synthesis of conjugated dienes via the addition of vinyl cuprates to acetylene
  作者：A. Alexakis、J.F. Normant

  DOI：10.1016/s0040-4039(00)85783-4

  日期：1982.1

  Some alkenyl cuprates add smoothly to acetylene yielding dienyl cuprates.

  一些链烯基铜酸酯可平滑地添加到乙炔中，从而生成二烯基铜酸酯。
• 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.
• Synthesis of Substituted 2-Pyridones via 6π-Electrocyclization of Dienyl Isocyanates
  作者：Xiayun Cheng、Alexandria P. Taylor、Kaicheng Zhu

  DOI：10.1021/acs.joc.2c00258

  日期：2022.5.6

  A one-pot Curtius rearrangement of dienyl carboxylic acids followed by a 6π-electrocyclization process to form substituted 2-pyridone products has been developed. Dienyl isocyanates generated from aliphatic acids were more reactive than their aromatic counterparts. Additionally, substitution patterns of the carboxylic acids had an impact on the efficiency of the cyclization.

  已经开发了二烯基羧酸的一锅Curtius重排，然后是6π-电环化过程以形成取代的2-吡啶酮产物。由脂肪酸生成的异氰酸二烯酯比其芳族对应物更具反应性。此外，羧酸的取代模式对环化效率有影响。