O,O'-dimethyl 2,6-pyridinedicarbothioate | 84877-69-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: O,O'-dimethyl 2,6-pyridinedicarbothioate
• 英文别名: O~2~,O~6~-Dimethyl pyridine-2,6-dicarbothioate；2-O,6-O-dimethyl pyridine-2,6-dicarbothioate
• CAS: 84877-69-0
• 化学式: C₉H₉NO₂S₂
• 分子量: 227.308
• InChiKey: PKCPRSCGAIVFOT-UHFFFAOYSA-N

物化性质

• 熔点：
  100-105 °C(Solv: methanol (67-56-1))
• 沸点：
  332.1±52.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  95.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  O,O'-dimethyl 2,6-pyridinedicarbothioate 在 对甲苯磺酸钠 、 镍 作用下， 以 四氢呋喃 、 二乙二醇二甲醚 为溶剂， 反应 12.0h， 生成 (4S,14S)-(+)-4,14-diphenyl-6,9,12-trioxa-3,15,21-triazabicyclo<15.3.1>heneicosa-1(21),17,19-triene
  参考文献：
  名称：

  New symmetrical chiral dibenzyl- and diphenyl-substituted diamido-, dithionoamido-, diaza-, and azapyridino-18-crown-6 ligands

  摘要：

  Eleven new chiral macrocycles (1-11, see Figure 1) of the pyridino-18-crown-6 type have been prepared. Nine diazapyridin-crown ligands contain two amide (1, R = benzyl; 4, R = phenyl), two N-methylamide (7, R = phenyl), two thionoamide (2, R = benzyl; 5, R = phenyl), two N-methylthionoamide (8, R = phenyl), two amine (3, R = benzyl; 6, R = phenyl), or two N-methylamine (9, R = phenyl) groups incorporated into the macroring. The appropriate chiral diamine was treated with dimethyl 2,6-pyridinedicarboxylate (or 2,6-pyridinedicarbonyl dichloride), O,O '-dimethyl 2,6-pyridinedicarbothioate, or 2,6-pyridinedimethyl ditosylate to prepare these materials. The macrocyclic diamides were also converted to the macrocyclic dithionoamides using Lawesson's reagent and the latter macrocycles were reduced to the diamines. A new symmetrically substituted dimethylazapyridino-18-crown-6 ligand (10) and its N-acetyl derivative 11 were also prepared. The interactions of some of the new chiral ligands with (R)- and (S)-[alpha-(l-naphthyl)ethyl]ammonium perchlorate were studied by H-1 NMR spectral techniques. The degree of enantiomeric recognition was determined by the difference of the free energy of activation values (DELTADELTAG double dagger) and the difference in log K values for these interactions. The X-ray analyses of the dithionoamido ligands (2, 5, and 8) showed severe deviations of the S and N atoms from the plane of the pyridine ring, especially in the case of 8. The optical rotation of 8 changed with time due to conformational changes. The relevant conformations of 8 are discussed in light of the X-ray crystallography, molecular mechanics, and H-1 NMR spectra.

  DOI：

  10.1021/jo00046a020
• 作为产物：
  描述：

  2,6-吡啶二甲腈 在 硫化氢 、 吡啶盐酸盐 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 17.0h， 生成 O,O'-dimethyl 2,6-pyridinedicarbothioate
  参考文献：
  名称：

  Preparation of macrocyclic polyether-thiono diester and -thiono tetraester ligands containing either the pyridine subcyclic unit or the oxalyl moiety, their complexes, and their reductive desulfurization to crown ethers

  摘要：

  DOI：

  10.1021/jo00164a001

文献信息

• Jones, Brian A.; Bradshaw, Jerald S.; Brown, Phillip R., Heterocycles, 1984, vol. 21, # 2, p. 386
  作者：Jones, Brian A.、Bradshaw, Jerald S.、Brown, Phillip R.、Davidson, Richard B.、Christensen, James J.、Izatt, Reed M.

  DOI：——

  日期：——
• Formation of ethers by the reductive desulfurization of thiono esters
  作者：Jerald S. Bradshaw、Brian A. Jones、James S. Gebhard

  DOI：10.1021/jo00155a048

  日期：1983.4
• BRADSHAW, J. S.;JONES, B. A.;GEBHARD, J. S., J. ORG. CHEM., 1983, 48, N 7, 1127-1129
  作者：BRADSHAW, J. S.、JONES, B. A.、GEBHARD, J. S.

  DOI：——

  日期：——
• JONES, B. A.;BRADSHAW, J. S.;BROWN, P. R.;CHRISTENSEN, J. J.;IZATT, R. M., J. ORG. CHEM., 1983, 48, N 16, 2635-2639
  作者：JONES, B. A.、BRADSHAW, J. S.、BROWN, P. R.、CHRISTENSEN, J. J.、IZATT, R. M.

  DOI：——

  日期：——
• JONES, B. A.;BRADSHAW, J. S.;BROWN, PH. R.;DAVIDSON, R. B.;CHRISTENSEN, J+, HETEROCYCLES, 1984, 21, N 2, 386
  作者：JONES, B. A.、BRADSHAW, J. S.、BROWN, PH. R.、DAVIDSON, R. B.、CHRISTENSEN, J+

  DOI：——

  日期：——