3,7-<(R)-(+)-1'-methylbenzyl>-1,5-dithia-3,7-diazacyclooctane | 156118-30-8

• 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: 3,7-<(R)-(+)-1'-methylbenzyl>-1,5-dithia-3,7-diazacyclooctane
• 英文别名: 3,7-bis[(1R)-1-phenylethyl]-1,5,3,7-dithiadiazocane
• CAS: 156118-30-8
• 化学式: C₂₀H₂₆N₂S₂
• 分子量: 358.572
• InChiKey: UOLBPSRUAIBYKK-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,7-<(R)-(+)-1'-methylbenzyl>-1,5-dithia-3,7-diazacyclooctane 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以63%的产率得到5-<(R)-(+)-1'-methylbenzyl>-1,3,5-dithiazine
  参考文献：
  名称：

  New chiral heterocycles: 5-[(r)-(+)-1′-methylbenzyyl-1,3,5-dithiazine and 3-7-di-[(R)-(+)-1′-methylbenzyu-3-7-diaza-1,5-dithiacyclooctane. Conformational studies and their reactions with borane.

  摘要：

  We report herein the syntheses of a new 5-[(R)-(+)-1'-methylbenzyl]-1,3,5-dithiazine 1, the 5-isopropyl-1,3,5-dithiazine 2 and the 3,7-di-[(R)-(+)-1'-methylbenzyl]-3,7-diaza-1,5-dithiacyclooctane 3, two of them (1 and 3) are new sulfur and nitrogen heterocycles bearing a chiral N-substituent. Compounds 1 and 2 were found in conformational equilibrium when observed at rt at H-1-270 MHz or C-13-67.8 MHz, when cooling a preferred chair conformation was observed with the N-substituent in the axial position. Heterocycle 3 was in an anchored crown conformation at rt. A conformational study of ring inversions for 1 and 3 was performed and their thermodynamic data were obtained, Delta G* = 48.1 +/- 0.8 for 1 and Delta G* = 64.8 +/- 1.2 kJ/mol for 3. The reactivity of 1-3 with BH3-THF was investigated, the N- or S-BH3 adducts were not stable, the reactions afforded cleanly the N-borane-N-dimethyl-N-alkylamine adducts. The reaction of 3 with BD3 gave the N-BD3 adduct of [CH2D]2N-CH[CH3]C6H5. An X-ray diffraction study of 3 confirmed its crown conformation with the N-substituents in pseudo-axial position.

  DOI：

  10.1016/0957-4166(94)80025-1
• 作为产物：
  描述：

  聚合甲醛 、 R(+)-alpha-甲基苄胺 在 sodium hydrogensulfide 作用下， 生成 3,7-<(R)-(+)-1'-methylbenzyl>-1,5-dithia-3,7-diazacyclooctane
  参考文献：
  名称：

  New chiral heterocycles: 5-[(r)-(+)-1′-methylbenzyyl-1,3,5-dithiazine and 3-7-di-[(R)-(+)-1′-methylbenzyu-3-7-diaza-1,5-dithiacyclooctane. Conformational studies and their reactions with borane.

  摘要：

  We report herein the syntheses of a new 5-[(R)-(+)-1'-methylbenzyl]-1,3,5-dithiazine 1, the 5-isopropyl-1,3,5-dithiazine 2 and the 3,7-di-[(R)-(+)-1'-methylbenzyl]-3,7-diaza-1,5-dithiacyclooctane 3, two of them (1 and 3) are new sulfur and nitrogen heterocycles bearing a chiral N-substituent. Compounds 1 and 2 were found in conformational equilibrium when observed at rt at H-1-270 MHz or C-13-67.8 MHz, when cooling a preferred chair conformation was observed with the N-substituent in the axial position. Heterocycle 3 was in an anchored crown conformation at rt. A conformational study of ring inversions for 1 and 3 was performed and their thermodynamic data were obtained, Delta G* = 48.1 +/- 0.8 for 1 and Delta G* = 64.8 +/- 1.2 kJ/mol for 3. The reactivity of 1-3 with BH3-THF was investigated, the N- or S-BH3 adducts were not stable, the reactions afforded cleanly the N-borane-N-dimethyl-N-alkylamine adducts. The reaction of 3 with BD3 gave the N-BD3 adduct of [CH2D]2N-CH[CH3]C6H5. An X-ray diffraction study of 3 confirmed its crown conformation with the N-substituents in pseudo-axial position.

  DOI：

  10.1016/0957-4166(94)80025-1

文献信息

• New chiral heterocycles: 5-[(r)-(+)-1′-methylbenzyyl-1,3,5-dithiazine and 3-7-di-[(R)-(+)-1′-methylbenzyu-3-7-diaza-1,5-dithiacyclooctane. Conformational studies and their reactions with borane.
  作者：Gregorio Cadenas-Pliego、Maria de Jésus Rosales-Hoz、Rosalinda Contreras、Angelina Flores-Parra

  DOI：10.1016/0957-4166(94)80025-1

  日期：1994.4

  We report herein the syntheses of a new 5-[(R)-(+)-1'-methylbenzyl]-1,3,5-dithiazine 1, the 5-isopropyl-1,3,5-dithiazine 2 and the 3,7-di-[(R)-(+)-1'-methylbenzyl]-3,7-diaza-1,5-dithiacyclooctane 3, two of them (1 and 3) are new sulfur and nitrogen heterocycles bearing a chiral N-substituent. Compounds 1 and 2 were found in conformational equilibrium when observed at rt at H-1-270 MHz or C-13-67.8 MHz, when cooling a preferred chair conformation was observed with the N-substituent in the axial position. Heterocycle 3 was in an anchored crown conformation at rt. A conformational study of ring inversions for 1 and 3 was performed and their thermodynamic data were obtained, Delta G* = 48.1 +/- 0.8 for 1 and Delta G* = 64.8 +/- 1.2 kJ/mol for 3. The reactivity of 1-3 with BH3-THF was investigated, the N- or S-BH3 adducts were not stable, the reactions afforded cleanly the N-borane-N-dimethyl-N-alkylamine adducts. The reaction of 3 with BD3 gave the N-BD3 adduct of [CH2D]2N-CH[CH3]C6H5. An X-ray diffraction study of 3 confirmed its crown conformation with the N-substituents in pseudo-axial position.