(2R,4aR,5aS,9aR,11aS)-2-Phenyl-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-8-one | 439264-70-7

• 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: (2R,4aR,5aS,9aR,11aS)-2-Phenyl-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-8-one
• 英文别名: (1S,3R,6R,8S,11R)-6-phenyl-2,5,7,12-tetraoxatricyclo[9.4.0.03,8]pentadecan-13-one
• CAS: 439264-70-7
• 化学式: C₁₇H₂₀O₅
• 分子量: 304.343
• InChiKey: HPLYELSKDJUUMS-LVNYTYFRSA-N

物化性质

• 熔点：
  189 °C(Solvent: Hexane; Dichloromethane)
• 沸点：
  500.8±50.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  (2R,4aR,5aS,9aR,11aS)-2-Phenyl-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-8-one 在 六甲基磷酰三胺 、 9-borabicyclo[3.3.1]nonane dimer 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 硼烷四氢呋喃络合物 、 双(三甲基硅烷基)氨基钾 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成
  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,9aS)-2-Phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-one 在 N,N-二甲基丙烯基脲 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 2,3-二甲基-2-丁烯 、 dimethyl sulfide borane 、 双(三甲基硅烷基)氨基钾 、 铜 、 potassium bromide 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 水 、 苯 为溶剂， 反应 6.5h， 生成 (2R,4aR,5aS,9aR,11aS)-2-Phenyl-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-8-one
  参考文献：
  名称：

  通过钯催化的乙烯酮缩醛三氟甲磺酸酯和有机锌试剂的偶联，可以轻松合成环状醚。在多环醚的迭代合成中的应用。

  摘要：

  在催化量的Pd（PPh（3））（4）存在下，乙烯酮缩醛三氟甲磺酸酯9a-e和均烯酸锌10的反应以良好的产率得到烯醇醚11a-e。通过硼氢化和内酯化将产物转化为相应的环醚14a和14b。本方法学使我们能够以简明的方式合成甘比罗尔的DE和GH环段。还描述了多环醚26和32的迭代合成。

  DOI：

  10.1021/jo025566f

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。
• Concise synthesis of cyclic ethers via the palladium-catalyzed coupling of ketene acetal triflates and a zinc homoenolate. Synthesis of the DE and GH ring segments of gambierol
  作者：Isao Kadota、Hiroyoshi Takamura、Kumi Sato、Yoshinori Yamamoto

  DOI：10.1016/s0040-4039(01)00824-3

  日期：2001.7

  Concise syntheses: of the DE and GH ring segments of gambierol (1) were achieved by the palladium-catalyzed coupling of ketene acetal triflates and a zinc homoenolate, followed by the hydroboration of the resulting cyclic enol ethers and subsequent lactonization. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.
• Concise Synthesis of Cyclic Ethers via the Palladium-Catalyzed Coupling of Ketene Acetal Triflates and Organozinc Reagents. Application to the Iterative Synthesis of Polycyclic Ethers
  作者：Isao Kadota、Hiroyoshi Takamura、Kumi Sato、Yoshinori Yamamoto

  DOI：10.1021/jo025566f

  日期：2002.5.1

  The reaction of the ketene acetal triflates 9a-e and a zinc homoenolate 10 in the presence of a catalytic amount of Pd(PPh(3))(4) gave the enol ethers 11a-e in good yields. The products were converted to the corresponding cyclic ethers 14a and 14b by hydroboration and lactonization. The present methodology allowed us to synthesize the DE and GH ring segment of gambierol in a concise manner. Iterative

  在催化量的Pd（PPh（3））（4）存在下，乙烯酮缩醛三氟甲磺酸酯9a-e和均烯酸锌10的反应以良好的产率得到烯醇醚11a-e。通过硼氢化和内酯化将产物转化为相应的环醚14a和14b。本方法学使我们能够以简明的方式合成甘比罗尔的DE和GH环段。还描述了多环醚26和32的迭代合成。