ethyl 3-methoxy-4,5-methylenedioxycinnamate | 123251-28-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl 3-methoxy-4,5-methylenedioxycinnamate
• 英文别名: (E)-ethyl 3-(7-methoxybenzo[d][1,3]dioxol-5-yl)acrylate；ethyl (E)-3-(7-methoxy-1,3-benzodioxol-5-yl)prop-2-enoate
• CAS: 123251-28-5
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: BIWOWHMPPIUKBO-SNAWJCMRSA-N

物化性质

• 熔点：
  76 °C
• 沸点：
  370.9±37.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-methoxy-4,5-methylenedioxycinnamate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.5h， 以81%的产率得到3-methoxy-4,5-methylenedioxycinnamyl alcohol
  参考文献：
  名称：

  Tanoguchi, Mariko; Kashima, Tatsuhiko; Saika, Hideyuki, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 1, p. 68 - 72

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-methylenedioxy-trans-cinnamic acid 在 盐酸 、 硫酸 、 硝酸 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 10.5h， 生成 ethyl 3-methoxy-4,5-methylenedioxycinnamate
  参考文献：
  名称：

  Synthesis, characterization, antidepressant and antioxidant activity of novel piperamides bearing piperidine and piperazine analogues

  摘要：

  A series of piperamide derivatives (8a-j) was synthesized with various substituted piperidine and piperazine compounds. The prepared compounds were evaluated for antibacterial activity against gram-positive and gram-negative bacteria and antifungal activity by disc diffusion method. The antioxidant activity of the compounds was evaluated by DPPH and superoxide radical scavenging method and antidepressant activity using forced swim and tail suspension behavioral despair tests in mice. The compounds 8a, 8b and 8c were investigated for their monoamine oxidase A and B (MAO-A and MAO-B) inhibitory property. Some of the test compounds were active in forced swim test (FST) and tail suspension test (TST). Compounds 8a and 8b showed a significant effect, when compared to standard drug, clorgyline. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.089

文献信息

• Phosphorylated cyclopropanes in the synthesis of α-alkylidene-γ-butyrolactones: total synthesis of (±)-savinin, (±)-gadain and (±)-peperomin E
  作者：Matthew G. Lloyd、Richard J. K. Taylor、William P. Unsworth

  DOI：10.1039/c6ob01527a

  日期：——

  Phosphorylated cyclopropanes, generated via the Rh(II)-catalysed intramolecular cyclopropanation of α-(diethoxyphosphoryl)acetates, have been found to be useful precursors in the synthesis of α-alkylidene-γ-butyrolactones. These cyclopropyl intermediates undergo regioselective reductive ring-opening and subsequent Horner–Wadsworth–Emmons olefination to complete the synthesis. Total syntheses of (±)-savinin

  已经发现，通过Rh（II）催化的α-（二乙氧基磷酰基）乙酸酯的分子内环丙烷化生成的磷酸化环丙烷是α-亚烷基-γ-丁内酯合成中的有用前体。这些环丙基中间体会进行区域选择性还原性开环反应，随后进行Horner-Wadsworth-Emmons烯化反应以完成合成。（±）-savinin和（±）-gadain的总合成，以及（±）-peperomin E的第一个总合成，均使用此方法进行了描述。
• Rajasekhar, Dodda; Subbaraju, Gottumukkala V., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 7, p. 837 - 838
  作者：Rajasekhar, Dodda、Subbaraju, Gottumukkala V.

  DOI：——

  日期：——
• TANOGUCHI, MARIKO;KASHIMA, TATSUHIKO;SAIKA, HIDEYUKI;INOUE, TAISHI;ARIMOT+, CHEM. AND PHARM. BULL., 37,(1989) N, C. 68-72
  作者：TANOGUCHI, MARIKO、KASHIMA, TATSUHIKO、SAIKA, HIDEYUKI、INOUE, TAISHI、ARIMOT+

  DOI：——

  日期：——
• Synthesis, characterization, antidepressant and antioxidant activity of novel piperamides bearing piperidine and piperazine analogues
  作者：M.K. Prashanth、Hosakere D. Revanasiddappa、K.M. Lokanatha Rai、B. Veeresh

  DOI：10.1016/j.bmcl.2012.09.089

  日期：2012.12

  A series of piperamide derivatives (8a-j) was synthesized with various substituted piperidine and piperazine compounds. The prepared compounds were evaluated for antibacterial activity against gram-positive and gram-negative bacteria and antifungal activity by disc diffusion method. The antioxidant activity of the compounds was evaluated by DPPH and superoxide radical scavenging method and antidepressant activity using forced swim and tail suspension behavioral despair tests in mice. The compounds 8a, 8b and 8c were investigated for their monoamine oxidase A and B (MAO-A and MAO-B) inhibitory property. Some of the test compounds were active in forced swim test (FST) and tail suspension test (TST). Compounds 8a and 8b showed a significant effect, when compared to standard drug, clorgyline. (C) 2012 Elsevier Ltd. All rights reserved.
• Tanoguchi, Mariko; Kashima, Tatsuhiko; Saika, Hideyuki, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 1, p. 68 - 72
  作者：Tanoguchi, Mariko、Kashima, Tatsuhiko、Saika, Hideyuki、Inoue, Taishi、Arimoto, Masao、Yamaguchi, Hideo

  DOI：——

  日期：——