5-Methylene-3,7-dioxanonane-1,9-diol ditosylate | 137378-08-6

• 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: 5-Methylene-3,7-dioxanonane-1,9-diol ditosylate
• 英文别名: 5-methylene-3,7-dioxa-1,9-nonadiyl ditosylate；2-[2-[2-(4-Methylphenyl)sulfonyloxyethoxymethyl]prop-2-enoxy]ethyl 4-methylbenzenesulfonate
• CAS: 137378-08-6
• 化学式: C₂₂H₂₈O₈S₂
• 分子量: 484.592
• InChiKey: NYVWVXJJHWVYLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-Methylene-3,7-dioxanonane-1,9-diol ditosylate 在 sodium hydroxide 、 苄基三乙基氯化铵 、 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 1',1'-Dichlorospiro[2,5,9,12-tetraoxabicyclo[11.4.0]heptadeca-1(17),13,15-triene-7,2'-cyclopropane]
  参考文献：
  名称：

  Czech, Bronislaw P.; Zazulak, Wolodymyr; Kumar, Anand, Journal of Heterocyclic Chemistry, 1991, vol. 28, # 5, p. 1387 - 1394

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2'-(2-methylenepropane-1,3-diyldioxy)bisethanol 、 对甲苯磺酰氯 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以86%的产率得到5-Methylene-3,7-dioxanonane-1,9-diol ditosylate
  参考文献：
  名称：

  Synthesis and complexation properties of suitcase-shaped macrotricyclic and butterfly-shaped macrobicyclic polyether ligands

  摘要：

  Ten suitcase-shaped macrotricyclic polyethers (1-10) containing nitrogen and carbon bridgehead atoms have been synthesized. These new cage compounds were prepared by connecting together two hydroxymethyl-substituted or two secondary amine-containing butterfly-shaped macrobicyclic polyethers by means of linear bifunctional connecting groups. Intermediate bis(hydroxymethyl)-substituted butterfly-shaped macrobicyclic polyether 14 was prepared by treating N,N'-bis(2-hydroxyethyl)ethylenediamine with 5-methylene-3,7-dioxanonane-1,9-diyl ditosylate to give bislariat 1,4-diaza-13-crown-4 (11) which was cyclized with 3-chloro-2-(chloromethyl)-l-propene followed by hydroboration. Intermediate bissecondary amine-contaminating butterfly shaped macrobicyclic polyethers 18 and 19 were prepared by treating N,N'-bis(2-hydroxyethyl)ethylenediamine with 6-tosyl-3,9-dioxa-6-aza-1,11-undecanediyl ditosylate (33) to give N-tosyl-N,N"-bis(2-hydroxyethyl)triaza-15-crown-5 (12). Lariat crown ether 12 was cyclized with 33 followed by reduction with LiAlH4 to give 18, or with 4-tosyl-4-aza-1,7-heptanediyl ditosylate (36) to give 19. Some of the suitcase-shaped macrotricycles interacted with various cations. One was selective for Pb2+ ions and another interacted strongly with Hg2+. A crystal structure for the 13-NaClO4 complex also is reported.

  DOI：

  10.1021/jo00044a040

文献信息

• Bradshaw, Jerald S.; Krakowiak, Krzysztof E.; An, Haovyn, Journal of Heterocyclic Chemistry, 1992, vol. 29, # 6, p. 1429 - 1432
  作者：Bradshaw, Jerald S.、Krakowiak, Krzysztof E.、An, Haovyn、Izatt, Reed M.

  DOI：——

  日期：——
• Preparation and cation complexing properties of some macropolycyclic ligands
  作者：Krzysztof E. Krakowiak、Jerald S. Bradshaw、N. Kent Dalley、Chengyue Zhu、Guoliang Yi、Janet C. Curtis、Du Li、Reed M. Izatt

  DOI：10.1021/jo00037a038

  日期：1992.5

  Five new cryptands have been prepared by a 2:1 cyclocondensation of an alpha,omega-dihalide with an alpha,omega-diamine. In some cases, other products, such as bis(aza-12-crown-4) ligands and products of a 4:2 cyclocondensation, were isolated also. The structures of the cryptands and bis(aza-crown)s of the game molecular weight were established after careful analysis by C-13 NMR and X-ray spectroscopy and a few independent syntheses of the bis(aza-crown) ethers. A new TLC test has been developed to distinguish between the cryptands and the bis(aza-crown)s. Log K values for the interaction of two cryptands, each containing two propylene bridges in one arm, with various cations were determined. The results show a much weaker interaction of the cryptands containing two propylene bridges with various cations than that for the corresponding cryptands with only ethylene bridges. The most stable complexes of these new propylene-containing cryptands were those involving Ba2+ and Sr2+ ions. X-ray analyses of three cryptands, each of which has the [18]N2O4 macrocycle as part of its structure, show different organizations for the ring heteroatoms.
• Synthesis and complexation properties of new unsymmetrical cryptands
  作者：Jerald S. Bradshaw、Haoyun An、Krzysztof E. Krakowiak、Tingmin Wang、Chengyue Zhu、Reed M. Izatt

  DOI：10.1021/jo00049a013

  日期：1992.11

  Twelve novel unsymmetrical cryptands (1-12) containing various units (methylene, 2-methylenylpropylene, pyridine-2,6-diyldimethylene, o- and m-xylylene) each in two bridges have been synthesized by a one-step cyclization procedure. These cryptands were obtained by treating tetraalcohols 15-17, obtained from diethanolamine and diglycolyl dichloride followed by reduction or from diethanolamine and the appropriate oligoethylene glycol dichloride or ditosylate, with methylene chloride, 3-chloro-2-(chloromethyl)-l-propene, alpha,alpha'-dibromo-o-xylene, alpha,alpha'-dibromo-m-xylene, and 2,6-pyridinediyldimethyl ditosylate. Cryptancls 7 and 11, containing two acetal functions, were obtained in yields of 59 and 40%, respectively. Bis(2-methylenepropylene)-bridged cryptand 4 was independently synthesized by another method. Complexation properties of nearly all of these cryptands with the alkali metal cations were studied by an NMR technique. Some of the results were verified by a calorimetric titration technique. Cryptands 5 and 9, containing a 2,6-pyridinediyldimethylene unit in two bridges, and 11, containing a methylene unit in two bridges, showed high selectivity for potassium over sodium ions by factors ranging from 40 to 200. Bisacetal-containing cryptand 7 exhibited high selectivity for sodium over potassium ions with a selectivity factor of over 1000.
• Bradshaw Jerald S., Krakowiak Krzysztof E., An Haoyun, Izatt Reed M., J. Heterocycl. Chem., 29 (1992) N 6, S 1429-1432
  作者：Bradshaw Jerald S., Krakowiak Krzysztof E., An Haoyun, Izatt Reed M.

  DOI：——

  日期：——
• Czech, Bronislaw P.; Zazulak, Wolodymyr; Kumar, Anand, Journal of Heterocyclic Chemistry, 1991, vol. 28, # 5, p. 1387 - 1394
  作者：Czech, Bronislaw P.、Zazulak, Wolodymyr、Kumar, Anand、Dalley, N. Kent、Weiming, Jiang、Bartsch, Richard A.

  DOI：——

  日期：——