(E)-3-((2R,4aR,6S,7R,9aS)-7-Hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-acrylic acid methyl ester | 440333-72-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (E)-3-((2R,4aR,6S,7R,9aS)-7-Hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-acrylic acid methyl ester
• 英文别名: methyl (E)-3-[(2R,4aR,6S,7R,9aS)-7-hydroxy-2-phenyl-4a,6,7,8,9,9a-hexahydro-4H-[1,3]dioxino[5,4-b]oxepin-6-yl]prop-2-enoate
• CAS: 440333-72-2
• 化学式: C₁₈H₂₂O₆
• 分子量: 334.369
• InChiKey: DKJAGCYMQDJXBX-NKIKVDIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-3-((2R,4aR,6S,7R,9aS)-7-Hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-acrylic acid methyl ester 在 palladium on activated charcoal 六甲基磷酰三胺 、 camphor-10-sulfonic acid 、 氢气 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 (1S,3R,6R,8S,11R,13S,14R)-13-[3-[tert-butyl(dimethyl)silyl]oxypropyl]-6-(4-methoxyphenyl)-2,5,7,12-tetraoxatricyclo[9.4.0.03,8]pentadecan-14-ol
  参考文献：
  名称：

  Design and synthesis of simplified polycyclic ethers and evaluation of their interaction with an α-helical peptide as a model of target proteins

  摘要：

  Two simplified pentacyclic ethers, having 6/7/6/6/7 and 6/7/6/7/7 ring systems, were synthesized. A convergent route based on the Suzuki-Miyaura cross-coupling strategy was applied to synthesize these two compounds. Interactions between a-helical peptide, melittin, and synthesized pentacyclic ethers were evaluated by circular dichroism (CD) spectroscopy. Interestingly, only the polycyclic ether having a 6/7/6/7/7 ring stabilized the a-helical structure of melittin. This result indicated that a ring fusion manner of the polycyclic structure is important to recognize membrane proteins. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.041
• 作为产物：
  描述：

  (2R,4aR,6S,7R,9aS)-6-ethenyl-2-phenyl-4a,6,7,8,9,9a-hexahydro-4H-[1,3]dioxino[5,4-b]oxepin-7-ol 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-3-((2R,4aR,6S,7R,9aS)-7-Hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-acrylic acid methyl ester
  参考文献：
  名称：

  甘比罗尔AB和EFGH环段的合成

  摘要：

  描述了冈比亚醇（1）的AB和EFGH环系统的立体控制合成。由2-脱氧-d-核糖经线性序列制备代表AB和EFGH环骨架的两个关键中间体3和55。布朗的不对称烯丙基硼化和分子内异迈克尔反应成功地应用于A环部分的建设。EFGH环段55的合成是通过SmI 2实现的介导的还原环化反应，构建了带有两个1,3-双轴甲基的EF环，以及钯催化的三氟甲磺酸烯醇盐和双歧烯酸锌的偶联，从而形成了GH环部分。还介绍了针对EFGH环框架的尝试收敛方法。

  DOI：

  10.1016/s0040-4020(02)00039-x

文献信息

• Syntheses of the AB and EFGH ring segments of gambierol
  作者：Isao Kadota、Chie Kadowaki、Choul-Hong Park、Hiroyoshi Takamura、Kumi Sato、Philip W.H Chan、Stephan Thorand、Yoshinori Yamamoto

  DOI：10.1016/s0040-4020(02)00039-x

  日期：2002.3

  described. The two key intermediates 3 and 55, representing the AB and EFGH ring frameworks, were prepared from 2-deoxy-d-ribose via linear sequences. Brown's asymmetric allylboration and the intramolecular hetero-Michael reaction were successfully applied to the construction of the A ring moiety. Synthesis of the EFGH ring segment 55 was achieved by the SmI2 mediated reductive cyclization, constructing

  描述了冈比亚醇（1）的AB和EFGH环系统的立体控制合成。由2-脱氧-d-核糖经线性序列制备代表AB和EFGH环骨架的两个关键中间体3和55。布朗的不对称烯丙基硼化和分子内异迈克尔反应成功地应用于A环部分的建设。EFGH环段55的合成是通过SmI 2实现的介导的还原环化反应，构建了带有两个1,3-双轴甲基的EF环，以及钯催化的三氟甲磺酸烯醇盐和双歧烯酸锌的偶联，从而形成了GH环部分。还介绍了针对EFGH环框架的尝试收敛方法。
• Design and synthesis of simplified polycyclic ethers and evaluation of their interaction with an α-helical peptide as a model of target proteins
  作者：Masato Sasaki、Kazuo Tachibana

  DOI：10.1016/j.tetlet.2007.03.041

  日期：2007.4

  Two simplified pentacyclic ethers, having 6/7/6/6/7 and 6/7/6/7/7 ring systems, were synthesized. A convergent route based on the Suzuki-Miyaura cross-coupling strategy was applied to synthesize these two compounds. Interactions between a-helical peptide, melittin, and synthesized pentacyclic ethers were evaluated by circular dichroism (CD) spectroscopy. Interestingly, only the polycyclic ether having a 6/7/6/7/7 ring stabilized the a-helical structure of melittin. This result indicated that a ring fusion manner of the polycyclic structure is important to recognize membrane proteins. (c) 2007 Elsevier Ltd. All rights reserved.