ethyl (E)-3-(4-(methoxymethoxy)phenyl)acrylate | 847450-00-4

• 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 (E)-3-(4-(methoxymethoxy)phenyl)acrylate
• 英文别名: Ethyl (2E)-3-[4-(methoxymethoxy)phenyl]-2-propenoate；ethyl (E)-3-[4-(methoxymethoxy)phenyl]prop-2-enoate
• CAS: 847450-00-4
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: OTEIJRLJNZRCCB-RMKNXTFCSA-N

物化性质

• 沸点：
  361.0±27.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (E)-3-(4-(methoxymethoxy)phenyl)acrylate 在 盐酸 、 4-二甲氨基吡啶 、 氢氧化钾 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 香豆酸肉桂酯
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Natural Ester Sintenin and Its Synthetic Analogues

  摘要：

  Synthesis of 3-(3,4-dimethoxyphenyl)propyl-3-(3,4-dimethoxyphenyl) propanoate (18), a cytotoxic natural ester, was carried out by a convenient synthetic path with a total yield of 49%. Sixteen of its analogues (19-34) were also prepared. Seventeen unsaturated derivatives of 18, compounds 1-17, were also synthesized to examine the structure-activity relationship of this type of ester. All of the synthetic compounds were passed through the cytotoxicity screenings on human tumor cell lines, such as PC-3, Hela, A549, BEL7404, CNE, and KB. Some of the esters exhibited moderate inhibitory effects on these tumor cell lines. The phenolic derivatives exhibited the highest cytotoxicity among these derivatives, while the unsaturated esters were more cytotoxic than the saturated analogues. Some of the compounds also exhibited inhibition on a-glucosidase.

  DOI：

  10.1021/np0496441
• 作为产物：
  描述：

  对羟基苯甲醛 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 ethyl (E)-3-(4-(methoxymethoxy)phenyl)acrylate
  参考文献：
  名称：

  首次对映选择性全合成人 MAO 抑制剂 (+)-Colveol A

  摘要：

  我们提出了人类 MAO 抑制剂 (+)-colveol A 的第一个对映选择性全合成，并对 (+)-colveol B 的合成进行了初步研究。探索了以 Sharpless 不对称二羟基化为中心的三种策略来构建邻位顺式二羟基化系统。涉及查尔酮衍生物直接不对称二羟基化的最初尝试没有成功。或者，(+)-colveol A 的成功合成路线涉及肉桂酯的 Sharpless 二羟基化、间苯二酚部分的格氏加成、Wittig 反应和 BBr 3介导的 MOM 醚的整体脱保护作为关键步骤。(+)-colveol A 的合成经过 7 个步骤，收率为 30%。

  DOI：

  10.1016/j.tet.2023.133778

文献信息

• 10.1039/d4ob00858h
  作者：Kamo, Shogo、Hori, Kazuki、Sugita, Kazuyuki

  DOI：10.1039/d4ob00858h

  日期：——

  chemoselective one-pot cleavage and oxidation of silyl ethers using catalytic amount of TsOH·H2O and IBX in DMSO. The oxidation of primary alkyl TBS ethers afforded the corresponding aldehydes in 51–94% yields, in the presence of aryl TBS, MOM, and PMB ethers, as well as N-Boc and acetonide groups. Secondary benzyl TBS ethers bearing aryl TBS ethers were also oxidized to ketones in moderate yields. A

  在此，我们描述了使用催化量的TsOH·H 2 O和IBX在DMSO中的化学选择性一锅裂解和氧化硅醚。在芳基 TBS、MOM 和 PMB 醚以及N -Boc 和丙酮基团存在下，伯烷基 TBS 醚的氧化得到相应的醛，产率为 51-94%。带有芳基 TBS 醚的仲苄基 TBS 醚也以中等产率氧化成酮。还提出了可能的反应途径。
• Synthesis and Biological Evaluation of a Natural Ester Sintenin and Its Synthetic Analogues
  作者：Li Hong Hu、Hong Bin Zou、Jing Xu Gong、Hai Bo Li、Lei Xiang Yang、Wei Cheng、Chang Xin Zhou、Hua Bai、Françoise Guéritte、Yu Zhao

  DOI：10.1021/np0496441

  日期：2005.3.1

  Synthesis of 3-(3,4-dimethoxyphenyl)propyl-3-(3,4-dimethoxyphenyl) propanoate (18), a cytotoxic natural ester, was carried out by a convenient synthetic path with a total yield of 49%. Sixteen of its analogues (19-34) were also prepared. Seventeen unsaturated derivatives of 18, compounds 1-17, were also synthesized to examine the structure-activity relationship of this type of ester. All of the synthetic compounds were passed through the cytotoxicity screenings on human tumor cell lines, such as PC-3, Hela, A549, BEL7404, CNE, and KB. Some of the esters exhibited moderate inhibitory effects on these tumor cell lines. The phenolic derivatives exhibited the highest cytotoxicity among these derivatives, while the unsaturated esters were more cytotoxic than the saturated analogues. Some of the compounds also exhibited inhibition on a-glucosidase.
• First enantioselective total synthesis of human MAO inhibitor (+)-Colveol A
  作者：Keerthana S、Sowbarnika Senthilkumar、Rajendar Goreti

  DOI：10.1016/j.tet.2023.133778

  日期：2024.1

  preliminary studies toward the synthesis of (+)-colveol B. Three strategies, centered on Sharpless asymmetric dihydroxylation, were explored to construct the vicinal syn-dihydroxyl system. The initial attempt involving direct asymmetric dihydroxylation of a chalcone derivative was unsuccessful. Alternatively, successful synthetic routes for (+)-colveol A involved Sharpless dihydroxylation of a cinnamyl

  我们提出了人类 MAO 抑制剂 (+)-colveol A 的第一个对映选择性全合成，并对 (+)-colveol B 的合成进行了初步研究。探索了以 Sharpless 不对称二羟基化为中心的三种策略来构建邻位顺式二羟基化系统。涉及查尔酮衍生物直接不对称二羟基化的最初尝试没有成功。或者，(+)-colveol A 的成功合成路线涉及肉桂酯的 Sharpless 二羟基化、间苯二酚部分的格氏加成、Wittig 反应和 BBr 3介导的 MOM 醚的整体脱保护作为关键步骤。(+)-colveol A 的合成经过 7 个步骤，收率为 30%。