7-Thia-14,15-diaza-dispiro[5.1.5.2]pentadec-14-ene-3,11-dione | 99921-97-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-Thia-14,15-diaza-dispiro[5.1.5.2]pentadec-14-ene-3,11-dione
• 英文别名: 7-Thia-14,15-diazadispiro[5.1.58.26]pentadec-14-ene-3,11-dione
• CAS: 99921-97-8
• 化学式: C₁₂H₁₆N₂O₂S
• 分子量: 252.337
• InChiKey: ADRITIOLBJYMFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  84.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-Thia-14,15-diaza-dispiro[5.1.5.2]pentadec-14-ene-3,11-dione 在 硫化氢 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 生成 7,12,17-Trithia-24,25,28,29,32,33-hexazahexaspiro[5.1.2.1.2.1.518.216.213.211.28.26]tritriacont-28-ene
  参考文献：
  名称：

  Oligo(cyclohexylidenes): Parent Compounds and End-Functionalized Derivatives

  摘要：

  Parent oligo(cyclohexylidenes) 1(n) (n = 1-4) were synthesized using a modified Barton-Kellogg olefin synthesis. Surprisingly, the crude compounds 1(2) and 1(4) contained small amounts of the 1(n-1) and 1(n+1) homologues. As evidenced by a close examination of mass spectral data of selectively deuterated tercyclohexylidenes 1(2)d(4)d(4) and 1(2)-d(8), their formation can be attributed to scrambling of the intermediate azines. With increasing n, a marked decrease in solubility as well as an increase in thermal stability was found. Powder diffraction measurements indicate that the parent compounds 1(n), irrespective of n, pack in a similar fashion in the solid state. The theoretically (MMX, AM1, and ab initio) predicted rodlike structure of the oligo(cyclohexylidenes) was confirmed by single-crystal X-ray structures of 1(1) and three derivatives (12(1), 13(1), and 30(2)). In line with the powder diffraction data in the series 1(n), a similar packing motif was found for the derivatives. To circumvent side product formation due to azine scrambling, a different synthetic approach was used for the preparation of end-functionalized oligo(cyclohexylidenes), i.e. decarboxylation and dehydration of beta-hydroxy acids.

  DOI：

  10.1021/jo00119a014
• 作为产物：
  描述：

  1,4,14,17-Tetraoxa-9-thia-20,21-diazatetraspiro<4.2.1.2.4.2.2.2>tricos-20-en 在 oxonium 作用下， 以 二氯甲烷 为溶剂， 生成 7-Thia-14,15-diaza-dispiro[5.1.5.2]pentadec-14-ene-3,11-dione
  参考文献：
  名称：

  Oligo(cyclohexylidenes): Parent Compounds and End-Functionalized Derivatives

  摘要：

  Parent oligo(cyclohexylidenes) 1(n) (n = 1-4) were synthesized using a modified Barton-Kellogg olefin synthesis. Surprisingly, the crude compounds 1(2) and 1(4) contained small amounts of the 1(n-1) and 1(n+1) homologues. As evidenced by a close examination of mass spectral data of selectively deuterated tercyclohexylidenes 1(2)d(4)d(4) and 1(2)-d(8), their formation can be attributed to scrambling of the intermediate azines. With increasing n, a marked decrease in solubility as well as an increase in thermal stability was found. Powder diffraction measurements indicate that the parent compounds 1(n), irrespective of n, pack in a similar fashion in the solid state. The theoretically (MMX, AM1, and ab initio) predicted rodlike structure of the oligo(cyclohexylidenes) was confirmed by single-crystal X-ray structures of 1(1) and three derivatives (12(1), 13(1), and 30(2)). In line with the powder diffraction data in the series 1(n), a similar packing motif was found for the derivatives. To circumvent side product formation due to azine scrambling, a different synthetic approach was used for the preparation of end-functionalized oligo(cyclohexylidenes), i.e. decarboxylation and dehydration of beta-hydroxy acids.

  DOI：

  10.1021/jo00119a014

文献信息

• MCMURRY, J. E.;HALEY, G. J.;MATZ, J. R.;CLARDY, J. C.;MITCHELL, J., J. AMER. CHEM. SOC., 1986, 108, N 3, 515-516
  作者：MCMURRY, J. E.、HALEY, G. J.、MATZ, J. R.、CLARDY, J. C.、MITCHELL, J.

  DOI：——

  日期：——
• Pentacyclo[12.2.2.22,5.26,9.210,13]-1,5,9,13-tetracosatetraene and its reaction with silver trifluoromethanesulfonate. Synthesis of a square-planar d10 organometallic complex
  作者：John E. McMurry、Gregory J. Haley、James R. Matz、Jon C. Clardy、John. Mitchell

  DOI：10.1021/ja00263a032

  日期：1986.2
• Oligo(cyclohexylidenes): Parent Compounds and End-Functionalized Derivatives
  作者：Frans J. Hoogesteger、Remco W. A. Havenith、Jan W. Zwikker、Leonardus W. Jenneskens、Huub Kooijman、Nora Veldman、Anthony L. Spek

  DOI：10.1021/jo00119a014

  日期：1995.7

  Parent oligo(cyclohexylidenes) 1(n) (n = 1-4) were synthesized using a modified Barton-Kellogg olefin synthesis. Surprisingly, the crude compounds 1(2) and 1(4) contained small amounts of the 1(n-1) and 1(n+1) homologues. As evidenced by a close examination of mass spectral data of selectively deuterated tercyclohexylidenes 1(2)d(4)d(4) and 1(2)-d(8), their formation can be attributed to scrambling of the intermediate azines. With increasing n, a marked decrease in solubility as well as an increase in thermal stability was found. Powder diffraction measurements indicate that the parent compounds 1(n), irrespective of n, pack in a similar fashion in the solid state. The theoretically (MMX, AM1, and ab initio) predicted rodlike structure of the oligo(cyclohexylidenes) was confirmed by single-crystal X-ray structures of 1(1) and three derivatives (12(1), 13(1), and 30(2)). In line with the powder diffraction data in the series 1(n), a similar packing motif was found for the derivatives. To circumvent side product formation due to azine scrambling, a different synthetic approach was used for the preparation of end-functionalized oligo(cyclohexylidenes), i.e. decarboxylation and dehydration of beta-hydroxy acids.