2,2',3,3'-tetramethoxy-9,9'-bitriptycyl | 171002-51-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,2',3,3'-tetramethoxy-9,9'-bitriptycyl
• 英文别名: 1-(4,5-Dimethoxy-1-pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaenyl)-4,5-dimethoxypentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaene
• CAS: 171002-51-0；171229-22-4；217455-59-9；217455-60-2
• 化学式: C₄₄H₃₄O₄
• 分子量: 626.752
• InChiKey: VMRNNEQNMZLXGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  48
• 可旋转键数：
  5
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2',3,3'-tetramethoxy-9,9'-bitriptycyl 在 乙硫醇钠 作用下， 生成 (+/-)-3,3'-dihydroxy-2,2'-dimethoxy-9,9'-bitriptycyl
  参考文献：
  名称：

  Syntheses of ap- and ±sc-2,2′,3,3′-tetramethoxy-9,9′-bitriptycyl rotamers and optical resolution of the ±sc-form

  摘要：

  Rotational isomers of 2,2',3,3'-tetramethoxy-9,9'-bitriptycyl, of which ap form is of C-2h symmetry whereas the sc forms Ct, have been isolated. The optically active forms exhibit the following specific rotations at Na D line for chloroform solutions (concentration ca. 1%) at 25 degrees C: Dextrorotatory form +7.8 degrees, levorotatory form -7.6 degrees.

  DOI：

  10.1016/0040-4039(95)01264-i
• 作为产物：
  描述：

  环己-1,3-二烯-5-炔 、 2,2',3,3'-tetramethoxy-9,9'-bianthryl 以15%的产率得到2,2',3,3'-tetramethoxy-9,9'-bitriptycyl
  参考文献：
  名称：

  Syntheses of ap- and ±sc-2,2′,3,3′-tetramethoxy-9,9′-bitriptycyl rotamers and optical resolution of the ±sc-form

  摘要：

  Rotational isomers of 2,2',3,3'-tetramethoxy-9,9'-bitriptycyl, of which ap form is of C-2h symmetry whereas the sc forms Ct, have been isolated. The optically active forms exhibit the following specific rotations at Na D line for chloroform solutions (concentration ca. 1%) at 25 degrees C: Dextrorotatory form +7.8 degrees, levorotatory form -7.6 degrees.

  DOI：

  10.1016/0040-4039(95)01264-i

文献信息

• Absolute Conformation and Chiroptical Properties. VI. 2,2′,3,3′-Tetramethoxy-9,9′-bitriptycyl: A Stereochemical Analog of 1,2-Disubstituted Ethane with Identical Substituents
  作者：Shinji Toyota、Akihiro Yasutomi、Hiroharu Kojima、Yuko Igarashi、Mitsuhiro Asakura、Michinori Oki

  DOI：10.1246/bcsj.71.2715

  日期：1998.11

  3′-tetramethoxy-9,9′-bitriptycyl. The absolute conformation of the tetramethoxy compound was determined by X-ray structure analysis of 3′-ester of (1S,5R,7R)-4-(2-carboxybenzoyl)-3-thia-4-azatricyclo[5.2.1.01,5]decane 3,3-dioxide derived from 3-hydroxy-2,2′,3′-trimethoxy-9,9′-bitriptycyl, followed by hydrolysis and then methylation. The CD spectrum of Msc-2,2′,3,3′-tetramethoxy-9,9′-bitriptycyl is reported

  标题化合物通过将 4,5-二甲氧基苄加成至 9,9'-联芳基而制备。旋转异构体ap 和±sc 通过HPLC 分离。±sc 异构体用乙硫醇钠处理产生 3,3'-二羟基-2,2'-二甲氧基-9,9'-二三苯甲基，将其转化为 (1S,5R,7R)-4-[ (2-羧基)苯甲酰基]-3-thia-4-氮杂三环[5.2.1.01,5]癸烷3,3-二氧化物。所得非对映异构体通过HPLC分离。将异构体水解并用硫酸二甲酯甲基化，得到具有旋光活性的 2,2',3,3'-四甲氧基-9,9'-二三苯甲基。四甲氧基化合物的绝对构象通过(1S,5R,7R)-4-(2-羧基苯甲酰基)-3-thia-4-氮杂三环[5.2.1.01,5 ]癸烷 3,3-二氧化物衍生自 3-羟基-2,2',3'-三甲氧基-9,9'-二三萜，然后水解，然后甲基化。报道了 Msc-2,2',3,3'-四甲氧基-9,9'-二三苯甲基的 CD 谱。