3,5-(2',2''-bis(hydroxyethyl))-4-oxahexacyclo[5.4.1.0^2,6.0^3,10.0^5,9.0^8,11]dodecane | 189197-15-7

• 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-(2',2''-bis(hydroxyethyl))-4-oxahexacyclo[5.4.1.0^2,6.0^3,10.0^5,9.0^8,11]dodecane
• 英文别名: 3,5-bis(2-hydroxyethyl)-4-oxahexacyclo[5.4.1.0^2,6.0^3,10.0^5,9.0^8,11]dodecane；2-[6-(2-Hydroxyethyl)-5-oxahexacyclo[5.4.1.02,6.03,10.04,8.09,12]dodecan-4-yl]ethanol
• CAS: 189197-15-7
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: WTUZVCREYMNKLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-(2',2''-bis(hydroxyethyl))-4-oxahexacyclo[5.4.1.0^2,6.0^3,10.0^5,9.0^8,11]dodecane 在 palladium on activated charcoal 氢气 、 三溴化磷 、 sodium carbonate 、 sodium iodide 作用下， 以 甲醇 、 乙腈 、 苯 为溶剂， 20.0 ℃ 、379.21 kPa 条件下， 反应 48.0h， 生成 7,10,25-Trioxa-4,13-diazaheptacyclo[14.8.1.118,23.01,21.016,20.017,24.019,22]hexacosane
  参考文献：
  名称：

  通过电喷雾电离/四极杆离子阱质谱法评估笼状冠配体对重金属的结合选择性

  摘要：

  电喷雾电离（ESI）/四极离子阱质谱用于评估甲醇溶液中5个笼状冠醚和2个聚醚参考化合物的重金属结合选择性。通过比较ESI质谱强度来分析Hg2 +，Pb2 +，Cd2 +和Cu2 +的结合偏好，目的是开发这种方法来快速筛选新的合成配体的结合选择性。笼型化合物优先与Hg2 +结合，但笼型隐窝衍生物偏爱Pb2 +。对Hg2 +的偏爱源于氮或硫原子对于Hg2 +的线性配位的有利定位，而穴状衍生物因其较大的空穴尺寸而偏爱Pb2 +。

  DOI：

  10.1021/ac991125t
• 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 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 生成 3,5-(2',2''-bis(hydroxyethyl))-4-oxahexacyclo[5.4.1.0^2,6.0^3,10.0^5,9.0^8,11]dodecane
  参考文献：
  名称：

  Kruger, Hendrik G.; Ramdhani, Reshika, South African Journal of Chemistry, 2006, vol. 59, p. 71 - 74

  摘要：

  DOI：

文献信息

• 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.
• Synthesis of chiral pentacyclo-undecane ligands and their use in the enantioselective alkylation of benzaldehyde with diethylzinc
  作者：Grant A. Boyle、Thavendran Govender、Hendrik G. Kruger、Glenn E.M. Maguire

  DOI：10.1016/j.tetasy.2004.07.038

  日期：2004.9

  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.
• Marchand, Alan P.; Huang, Zilin; Lai, Huiguo, Heterocycles, 2004, vol. 62, p. 279 - 296
  作者：Marchand, Alan P.、Huang, Zilin、Lai, Huiguo、McKim, Artie S.、Brodbelt, Jennifer S.、Williams, Sheldon

  DOI：——

  日期：——
• Marchand, Alan P.; Huang, Zilin; Chen, Zhibing, Journal of Heterocyclic Chemistry, 2001, vol. 38, # 6, p. 1361 - 1368
  作者：Marchand, Alan P.、Huang, Zilin、Chen, Zhibing、Hariprakasha、Namboothiri、Brodbelt, Jennifer S.、Reyzer, Michelle L.

  DOI：——

  日期：——
• 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：——