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 | 205812-56-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 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
• CAS: 205812-56-2
• 化学式: C₂₉H₃₂O₇S₂
• 分子量: 556.701
• InChiKey: JWFSYQROUAODGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  38.0
• 可旋转键数：
  10.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  95.97
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-(+)-4-methyl-2-methylamino-pentan-1-ol 、 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 在 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 96.0h， 以62%的产率得到(2S)-2-[2-[6-[2-[[(2S)-1-hydroxy-4-methylpentan-2-yl]-methylamino]ethyl]-5-oxahexacyclo[5.4.1.02,6.03,10.04,8.09,12]dodecan-4-yl]ethyl-methylamino]-4-methylpentan-1-ol
  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：

  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

文献信息

• Synthesis and NMR elucidation of novel penta-cycloundecane amine derivatives as potential antituberculosis agents
  作者：Oluseye K. Onajole、Thavendran Govender、Maya Makatini、Hendrik G. Kruger

  DOI：10.1002/mrc.2305

  日期：2008.11

  The synthesis and NMR elucidation of five novel penta‐cycloundecane amine derivatives are reported. These compounds are potential antituberculosis agents. The 1H and 13C spectra showed major overlapping of methine signals of the cage skeleton making it extremely difficult to elucidate these compounds. The overlapping occurs as a result of the additions made to the carbonyl carbon (C‐8/C‐11) of the

  报道了五种新型五环十一烷胺衍生物的合成和核磁共振分析。这些化合物是潜在的抗结核药物。1H 和 13C 光谱显示笼骨架的次甲基信号主要重叠，因此很难阐明这些化合物。重叠是由于笼子的羰基碳 (C-8/C-11) 的添加而发生的。二维核磁共振技术被证明是克服这个问题的有用工具。报道的所有化合物都是内消旋化合物，因此不仅简化了 NMR 结构解析，而且确实使之成为可能。版权所有 © 2008 John Wiley & Sons, Ltd.
• 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 and alkali metal picrate extraction capabilities of novel, cage-functionalized diazacrown ethers. Effects of host preorganization on avidity and selectivity toward alkali metal picrates in solution
  作者：Alan P. Marchand、Artie S. McKim、Kaipenchery A. Kumar

  DOI：10.1016/s0040-4020(98)00823-0

  日期：1998.10

  The synthesis of a series of cage-functionalized bis(monoazacrown) ethers and bis(diazacrown) ethers is described. Alkali metal picrate extraction profiles have been determined for several members of this novel series of ionophores. The increased level of preorganization achieved when a cage-functionalized bis(diaza-crown) ether is incorporated into a "molecular box" results in higher levels of avidity and selectivity of the resulting host system toward alkali metal picrates in solution. (C) 1998 Elsevier Science 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：——
• Synthesis and Alkali Metal Picrate Extraction Studies of an Unusual Cage-functionalized Cryptand
  作者：Alan P. Marchand、H. K. Hariprakasha、Hyun-Soon Chong、Mohamed Takhi

  DOI：10.3987/com-00-s(i)6

  日期：——