3,5-diallyl-4-oxahexacyclo[5.4.1.0^2,6.0^3,10.0^5.9.0^8,11]dodecane | 423176-32-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,5-diallyl-4-oxahexacyclo[5.4.1.0^2,6.0^3,10.0^5.9.0^8,11]dodecane
• 英文别名: 4,6-Bis(prop-2-enyl)-5-oxahexacyclo[5.4.1.02,6.03,10.04,8.09,12]dodecane
• CAS: 423176-32-3
• 化学式: C₁₇H₂₀O
• 分子量: 240.345
• InChiKey: NIFJPWLXMIMWDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,5-diallyl-4-oxahexacyclo[5.4.1.0^2,6.0^3,10.0^5.9.0^8,11]dodecane 在 氢氧化钾 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 生成 2-[6-[2-(4-methylphenyl)sulfonyloxyethyl]-5-oxahexacyclo[5.4.1.02,6.03,10.04,8.09,12]dodecan-4-yl]ethyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Synthesis of chiral pentacyclo-undecane ligands and their use in the enantioselective alkylation of benzaldehyde with diethylzinc

  摘要：

  The synthesis of a new class of chiral pentacycloundecane cage annulated bidentate ligands is reported. This class of ligands can be used in many reactions that are catalysed by amino alcohol ligands. The ability of the chiral ligands to asymmetrically catalyse the reaction between diethylzinc and benzaldehyde was investigated. The cage annulated bidentate ligands have C, symmetry and showed poor to good enantioselectivity with high yields compared to previous systems reported using other amino alcohol ligands. An important conclusion from the results is that both ligands should be involved in the mechanism as the bidentate ligands gives much improved enantioselectivity when compared with a single chiral source molecule. This system could be utilised as a versatile probe for examining the reaction mechanism. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.038
• 作为产物：
  描述：

  五环[5.4.0.02,6.03,10.05,9]十一烷-8,11-二酮 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 3,5-diallyl-4-oxahexacyclo[5.4.1.0^2,6.0^3,10.0^5.9.0^8,11]dodecane
  参考文献：
  名称：

  Chemical speciation of copper(ii) diaminediamide derivative of pentacycloundecane—a potential anti-inflammatory agent

  摘要：

  在 25 °C 和 0.15 mol dmâ 离子强度下，通过玻璃电极电位法研究了铜 (II)、锌 (II) 和钙 (II) 与 3,5-二氨基二氨基-4-氧杂六环十二烷 (cageL) 的形成常数。 3.铜(II) 与cageL 形成比锌(II) 和钙(II) 更稳定的络合物。金属离子络合促进酰胺氮的去质子化和配位，从而导致 Cu2+ 的整体四方配位（紫外-可见电子光谱表明）。使用血浆模型进行的形态计算表明，锌 (II) 和钙 (II) 是体内铜 (II) 的良好竞争者。使用 64Cu 标记的 Cu(II)-cageL 进行的生物分布实验表明，24 小时后约 50% 剂量的复合物保留在体内。

  DOI：

  10.1039/b614878f

文献信息

• Facile Synthesis of Hydroxy-Substituted Thiacrown Ethers via Nucleophilic Ring Opening of Epoxides
  作者：Monika Stefaniak、Jarosław Romański

  DOI：10.1055/s-0037-1612249

  日期：2019.5

  possessing two unsubstituted hydroxy groups that can be easily functionalized. In addition, epoxides and macrocycles derived from Cookson’s birdcage diketone, were prepared. The nucleophilic ring opening of epoxides synthesis can be classified in the frame of click chemistry. Surprisingly, some of the prepared allyl substituted polyglycols as well as bis-epoxides, especially sulfur analogues, were prepared

  抽象的 以一步法制备标题硫杂冠醚，得到一系列具有两个易于取代的未取代羟基的独特大环。另外，制备了由库克森的鸟笼二酮衍生的环氧化物和大环化合物。环氧化物合成的亲核开环可以在点击化学的框架内分类。令人惊讶地，首次制备了一些制备的烯丙基取代的聚乙二醇以及双环氧化物，尤其是硫类似物。 以一步法制备标题硫杂冠醚，得到一系列具有两个易于取代的未取代羟基的独特大环。另外，制备了由库克森的鸟笼二酮衍生的环氧化物和大环化合物。环氧化物合成的亲核开环可以在点击化学的框架内分类。令人惊讶地，首次制备了一些制备的烯丙基取代的聚乙二醇以及双环氧化物，尤其是硫类似物。
• NMR elucidation of a novel (<i>S</i>)-pentacyclo-undecane bis-(4-phenyloxazoline) ligand and related derivatives
  作者：Grant A. Boyle、Thavendran Govender、Hendrik G. Kruger、Glenn E. M. Maguire、Tricia Naicker

  DOI：10.1002/mrc.2279

  日期：2008.12

  bis‐(4‐phenyloxazoline) and related pentacyclo‐undecane (PCU) derivatives is reported. Two‐dimensional NMR proved to be a powerful technique in overcoming the difficulties associated with the elucidation of these compounds when only one‐dimensional NMR data is utilized. A chiral substituent was introduced to both ‘arms’ of the PCU skeleton to produce derivatives 1–3. These derivatives display C1 symmetry with

  报道了新型配体 (S)-五环十一烷双-(4-苯基恶唑啉) 和相关五环十一烷 (PCU) 衍生物的 NMR 阐明。当仅使用一维 NMR 数据时，二维 NMR 被证明是克服与阐明这些化合物相关的困难的强大技术。将手性取代基引入 PCU 骨架的两个“臂”以产生衍生物 1-3。这些衍生物表现出 C1 对称性，所有笼原子都是不等价的。由于 1H 光谱中峰的重叠，这些非对映质子的鉴定非常困难。13C 光谱导致非等价碳的清晰分裂。与具有手性取代基的类似 PCU 衍生物相比，这是不寻常的，因为尚未报道所有非对映笼碳的分裂。衍生物 1-3 的核 Overhauser 增强光谱 (NOESY) 相关性证实了分子的不同构象，其中侧“臂”相对于笼子部分占据不同的方向。版权所有 © 2008 John Wiley & Sons, Ltd.
• Synthesis and transport studies of a new class of cage-annulated chiral macrocycles
  作者：Thavendran Govender、Humcha K. Hariprakasha、Hendrik G. Kruger、Alan P. Marchand

  DOI：10.1016/s0957-4166(03)00272-6

  日期：2003.6

  The synthesis of a new class of chiral pentacycloundecane cage annulated macrocycles is reported. The ability of the chiral hosts to transport racemic phenylglycine methyl ester enantioselectively through a chloroform membrane in a U-tube was compared to that of related pyridine macrocycles. The cage annulated macrocycles showed weak to moderate enantioselectivity and very high rates of transport compared

  报道了新型的手性五环十一烷笼环式大环化合物的合成。比较了手性宿主通过U形管中的氯仿膜对映体选择性地运输外消旋苯基甘氨酸甲酯的能力与相关吡啶大环化合物的能力。笼成环大环化合物呈弱到中等的对映选择性和相比以前的系统传输率很高使用相同的反离子（PF报道6 - ）。传输率通过改变到相对较硬的抗衡离子（CL减慢- ）。
• Kruger, Hendrik G.; Ramdhani, Reshika, South African Journal of Chemistry, 2006, vol. 59, p. 71 - 74
  作者：Kruger, Hendrik G.、Ramdhani, Reshika

  DOI：——

  日期：——
• Pentacyclo-undecane derived cyclic tetra-amines: Synthesis and evaluation as potent anti-tuberculosis agents
  作者：Oluseye K. Onajole、Karnishree Govender、Patrick Govender、Paul D. van Helden、Hendrik G. Kruger、Glenn E.M. Maguire、Karen Muthusamy、Manormoney Pillay、Ian Wiid、Thavendran Govender

  DOI：10.1016/j.ejmech.2009.07.015

  日期：2009.11

  As part of an ongoing effort to develop highly potent anti-tuberculosis agents, fourteen pentacycloundecane (PCU) tetra-amine compounds were synthesized and screened for their in vitro anti-mycobacterial activity against two TB strains, H37Rv and XDR 194 [an extensively drug-resistant strain of tuberculosis]. Using the broth macrodilution method, nitrofuranylamide based compounds (6a and 6b) showed almost similar activities against the H37Rv strain of Mycobacterium tuberculosis when compared with the control drug, ethambutol. N-Geranyl piperazine PCU (8a) and trans-trans farnesyl piperazine PCU (8b) were 3.2 and 3.7 times more potent than commercially available ethambutol. Both isoprenyl PCU tetra-amine derivatives and N-decyl piperazine PCU (9a) were highly active against the XDR 194 strain of tuberculosis with MICs in the range of 0.63-3.02 mu M. Cytotoxicities (IC50) of isoprenyl based compounds (8a, 8b) and compound 9a were tested on a mammalian cell line [MDBK (Madin Darby bovine kidney epithelium)] with values of 30, 24 and 25 mu M respectively. (C) 2009 Elsevier Masson SAS. All rights reserved.