(E)-ethyl 3-(cyclohex-3-en-1-yl)acrylate | 127117-24-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-ethyl 3-(cyclohex-3-en-1-yl)acrylate
• 英文别名: ethyl (E)-3-(cyclohex-3-enyl)acrylate；ethyl (E)-3-cyclohex-3-en-1-ylprop-2-enoate
• CAS: 127117-24-2
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: LWSAIPNOVZOFMP-CMDGGOBGSA-N

物化性质

• 沸点：
  249.5±19.0 °C(Predicted)
• 密度：
  1.047±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 3-(cyclohex-3-en-1-yl)acrylate 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以89%的产率得到(E)-3-(cyclohex-3-en-1-yl)-N,N-diethylacrylamide
  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
• 作为产物：
  描述：

  乙氧基乙炔 、 3-环己烯甲醛 在 9-碘-9-硼杂二环[3.3.1]壬烷 作用下， 生成 (E)-ethyl 3-(cyclohex-3-en-1-yl)acrylate
  参考文献：
  名称：

  使用卤代反应xv进行有机合成。BI-9-BBN-乙氧基乙炔加合物与醛类的高度化学选择性反应新合成α，β-不饱和酯

  摘要：

  B-碘-9-硼环[3.3.1]壬烷与乙氧基乙炔的反应形成的卤代加合物在非常温和的条件下与醛发生化学选择性反应。随后的水解后处理以良好的产率得到-α，β-不饱和酯。

  DOI：

  10.1016/s0040-4039(01)93472-0

文献信息

• 1,3-Diphenyldisiloxane Enables Additive-Free Redox Recycling Reactions and Catalysis with Triphenylphosphine
  作者：Courtney C. Aldrich、Joseph A. Buonomo、Malcolm S. Cole、Carter G. Eiden

  DOI：10.1055/s-0040-1707345

  日期：2020.12

  variants of the Wittig olefination, Appel halogenation, and Staudinger reduction. Triphenylphosphine-promoted catalytic recycling reactions were also facilitated by DPDS. Additive-free triphenylphosphine-promoted catalytic Staudinger reductions could even be performed at ambient temperature due to the rapid nature of phosphinimine reduction, for which we characterized kinetic and thermodynamic parameters

  摘要 最近报道的用1，3-二苯基二硅氧烷（DPDS）对氧化膦进行化学选择性还原开辟了在催化体系中无添加剂还原氧化膦的可能性。本文中，我们公开了使用这种新的还原剂作为维蒂希，施陶丁格和酒精取代反应中磷氧化还原循环的促进剂。DPDS已成功用于Wittig烯烃化，Appel卤化和Staudinger还原的室温无添加剂氧化还原循环变体。DPDS还促进了三苯膦促进的催化循环反应。由于膦亚胺还原的快速性质，无添加剂三苯膦促进的Staudinger催化还原甚至可以在环境温度下进行，为此我们表征了动力学和热力学参数。
• GOTTSCHALK K.; PACHALY P., ARCH. PHARM., 1979, 312, NO 10, 822-831
  作者：GOTTSCHALK K.、 PACHALY P.

  DOI：——

  日期：——
• SATOH, YOSHITAKA;TAYANO, TAKAO;HARA, SHOJI;SUZUKI, AKIRA, TETRAHEDRON LETT., 30,(1989) N8, C. 5153-5156
  作者：SATOH, YOSHITAKA、TAYANO, TAKAO、HARA, SHOJI、SUZUKI, AKIRA

  DOI：——

  日期：——
• 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.
• Organic synthesis using haloboration reaction xv. A new synthesis of α,β-unsaturated esters by the highly chemoselective reaction of B-I-9-BBN-ethoxyethyne adduct with aldehydes
  作者：Yoshitaka Satoh、Takao Tayano、Shoji Hara、Akira Suzuki

  DOI：10.1016/s0040-4039(01)93472-0

  日期：——

  A haloboration adduct, formed by the reaction of B-iodo-9-borabicyclo[3.3.1]nonanes with ethoxyethyne reacts with aldehydes chemoselectively under very mild conditions. The subsequent hydrolytic work-up affords -α,β-unsaturated esters in good yields.

  B-碘-9-硼环[3.3.1]壬烷与乙氧基乙炔的反应形成的卤代加合物在非常温和的条件下与醛发生化学选择性反应。随后的水解后处理以良好的产率得到-α，β-不饱和酯。