2,11-dithia-5,7,9,14,16,18-hexamethyl-6,15-dimethoxy[3.3](1,3)cyclophane | 849599-33-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,11-dithia-5,7,9,14,16,18-hexamethyl-6,15-dimethoxy[3.3](1,3)cyclophane
• 英文别名: 7,15-Dimethoxy-6,8,14,16,17,18-hexamethyl-3,11-dithiatricyclo[11.3.1.15,9]octadeca-1(17),5(18),6,8,13,15-hexaene；7,15-dimethoxy-6,8,14,16,17,18-hexamethyl-3,11-dithiatricyclo[11.3.1.15,9]octadeca-1(17),5(18),6,8,13,15-hexaene
• CAS: 849599-33-3
• 化学式: C₂₄H₃₂O₂S₂
• 分子量: 416.649
• InChiKey: ZTNLYROOULDOGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,11-dithia-5,7,9,14,16,18-hexamethyl-6,15-dimethoxy[3.3](1,3)cyclophane 在 三溴化硼 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 以11%的产率得到2,11-dithia-5,7,9,14,16,18-hexamethyl-6,15-dihydroxy[3.3](1,3)cyclophane
  参考文献：
  名称：

  Conformational behavior of dithia[n.3.3](1,3,5)cyclophanes and dithia[n.3.3](1,2,6)cyclophanes

  摘要：

  The conformational behavior of a series of crown-fused dithia[n.3.3](1,2,6)cyclophanes (126-CPs) and dithia[n.3.3](l,3,5)cyclophanes (135-CPs) was investigated by variable-temperature H-1 and C-13 NMR spectroscopy, X-ray crystallography and density functional theory (DFT) calculations. Single crystal X-ray structure analysis showed that two thia-bridges in 126-CPs adopted a pseudochair-pseudochair (cc) conformation and the cyclophane decks underwent a ring-tilting motion in the case of [10.3.3](1,2,6)cyclophane (1a). In contrast, the thia-bridges in 135-CPs took both cc and pseudoboat-pseudochair (bc) conformations, and the ring-tilting process was also found in [10.3.3](1,3,5)cyclophane (2a). Variable temperature H-1 NMR study revealed that there was no wobbling-motion for two thia-bridges in 126-CPs while thia-bridges in 135-CPs experienced a wobbling-process with a conformational barrier of 9.21 and 8.80 kcal mol(-1), respectively, for 2a and [13.3.3](1,3,5)cyclophane (2b). DFT calculations for the two cyclophanes series revealed that 126-CPs preferred a cc conformation which was consistent with the experimental observation; similarly, 135-CPs took a preferential cc conformation, agreeing with 2a having a predominant cc conformer (cc:bc ratio=70:30), but not 2b having a predominant bc conformer (cc:bc ratio= 15:85) in the solid state. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.027
• 作为产物：
  描述：

  2,4,6-trimethyl-3,5-bis(bromomethyl)anisole 在 氢氧化钾 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 23.0h， 生成 2,11-dithia-5,7,9,14,16,18-hexamethyl-6,15-dimethoxy[3.3](1,3)cyclophane
  参考文献：
  名称：

  Conformational behavior of dithia[n.3.3](1,3,5)cyclophanes and dithia[n.3.3](1,2,6)cyclophanes

  摘要：

  The conformational behavior of a series of crown-fused dithia[n.3.3](1,2,6)cyclophanes (126-CPs) and dithia[n.3.3](l,3,5)cyclophanes (135-CPs) was investigated by variable-temperature H-1 and C-13 NMR spectroscopy, X-ray crystallography and density functional theory (DFT) calculations. Single crystal X-ray structure analysis showed that two thia-bridges in 126-CPs adopted a pseudochair-pseudochair (cc) conformation and the cyclophane decks underwent a ring-tilting motion in the case of [10.3.3](1,2,6)cyclophane (1a). In contrast, the thia-bridges in 135-CPs took both cc and pseudoboat-pseudochair (bc) conformations, and the ring-tilting process was also found in [10.3.3](1,3,5)cyclophane (2a). Variable temperature H-1 NMR study revealed that there was no wobbling-motion for two thia-bridges in 126-CPs while thia-bridges in 135-CPs experienced a wobbling-process with a conformational barrier of 9.21 and 8.80 kcal mol(-1), respectively, for 2a and [13.3.3](1,3,5)cyclophane (2b). DFT calculations for the two cyclophanes series revealed that 126-CPs preferred a cc conformation which was consistent with the experimental observation; similarly, 135-CPs took a preferential cc conformation, agreeing with 2a having a predominant cc conformer (cc:bc ratio=70:30), but not 2b having a predominant bc conformer (cc:bc ratio= 15:85) in the solid state. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.027

文献信息

• Conformational behavior of dithia[n.3.3](1,3,5)cyclophanes and dithia[n.3.3](1,2,6)cyclophanes
  作者：Jian-Wei Xu、Ting-Ting Lin、Yee-Hing Lai

  DOI：10.1016/j.tet.2005.01.027

  日期：2005.2

  The conformational behavior of a series of crown-fused dithia[n.3.3](1,2,6)cyclophanes (126-CPs) and dithia[n.3.3](l,3,5)cyclophanes (135-CPs) was investigated by variable-temperature H-1 and C-13 NMR spectroscopy, X-ray crystallography and density functional theory (DFT) calculations. Single crystal X-ray structure analysis showed that two thia-bridges in 126-CPs adopted a pseudochair-pseudochair (cc) conformation and the cyclophane decks underwent a ring-tilting motion in the case of [10.3.3](1,2,6)cyclophane (1a). In contrast, the thia-bridges in 135-CPs took both cc and pseudoboat-pseudochair (bc) conformations, and the ring-tilting process was also found in [10.3.3](1,3,5)cyclophane (2a). Variable temperature H-1 NMR study revealed that there was no wobbling-motion for two thia-bridges in 126-CPs while thia-bridges in 135-CPs experienced a wobbling-process with a conformational barrier of 9.21 and 8.80 kcal mol(-1), respectively, for 2a and [13.3.3](1,3,5)cyclophane (2b). DFT calculations for the two cyclophanes series revealed that 126-CPs preferred a cc conformation which was consistent with the experimental observation; similarly, 135-CPs took a preferential cc conformation, agreeing with 2a having a predominant cc conformer (cc:bc ratio=70:30), but not 2b having a predominant bc conformer (cc:bc ratio= 15:85) in the solid state. (C) 2005 Elsevier Ltd. All rights reserved.