cis-2,2-dimethyl-3-phenyl-4--7-methoxychroman | 84394-27-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: cis-2,2-dimethyl-3-phenyl-4--7-methoxychroman
• 英文别名: cis-2,2-dimethyl-3-phenyl-4-[m-(β-pyrrolidinoethoxy)phenyl]-7-methoxychroman；1-[2-[3-[(3S,4R)-7-methoxy-2,2-dimethyl-3-phenyl-3,4-dihydrochromen-4-yl]phenoxy]ethyl]pyrrolidine
• CAS: 84394-27-4
• 化学式: C₃₀H₃₅NO₃
• 分子量: 457.613
• InChiKey: PLIUCEMVAGBJSL-FQLXRVMXSA-N

物化性质

• 沸点：
  554.5±50.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.26
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  30.93
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  cis-2,2-dimethyl-3-phenyl-4--7-methoxychroman 在 正丁基锂 作用下， 以 正己烷 、 二甲基亚砜 为溶剂， 反应 16.0h， 以85%的产率得到trans-2,2-dimethyl-3-phenyl-4--7-methoxychroman
  参考文献：
  名称：

  Antifertility agents. 38. Effect of the side chain and its position on the activity of 3,4-diarylchromans

  摘要：

  In a study of the effect of the substituent on the receptor binding affinity (RBA), estrogenicity, and antiimplantation (AI) activity in trans-3,4-diarylchromans, it has been found that demethylation of trans-2, 2-dimethyl-3-phenyl-4-[p-(beta-pyrrolidinoethoxy)phenyl]-7-methoxychroman (centchroman, 1) to the corresponding 7-hydroxy compound (7) results in a 20-fold increase in RBA (112%) without any appreciable change in AI activity. On the other hand, absence of the pyrrolidinoethyl group from the 4-phenyl residue (6) leads to a drop in both RBA and AI activity. A chain length of two to three carbon atoms and a pyrrolidino ring appear to be necessary for activity in these compounds. It has been found that while the trans isomers with the tertiary aminoalkoxy side chain in the para position of the 4-phenyl radical were the most active, in the corresponding cis-chromans and chromenes, analogues with this chain in the meta position were most active; the ortho substituted compounds of all these series were inactive. In 3-phenyl-substituted compounds, the trans isomer carrying the p-hydroxy substituent (33) was found to be the most active; the corresponding pyrrolidinoethyl ether (13) showed a lower order of activity. The implication of these observations on the mapping of the different subsites on the receptor has been discussed.

  DOI：

  10.1021/jm00358a026
• 作为产物：
  描述：

  2,3'-dihydroxy-4-methoxybenzophenone 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 丙酮 为溶剂， 反应 36.0h， 生成 cis-2,2-dimethyl-3-phenyl-4--7-methoxychroman
  参考文献：
  名称：

  Antifertility agents. 38. Effect of the side chain and its position on the activity of 3,4-diarylchromans

  摘要：

  In a study of the effect of the substituent on the receptor binding affinity (RBA), estrogenicity, and antiimplantation (AI) activity in trans-3,4-diarylchromans, it has been found that demethylation of trans-2, 2-dimethyl-3-phenyl-4-[p-(beta-pyrrolidinoethoxy)phenyl]-7-methoxychroman (centchroman, 1) to the corresponding 7-hydroxy compound (7) results in a 20-fold increase in RBA (112%) without any appreciable change in AI activity. On the other hand, absence of the pyrrolidinoethyl group from the 4-phenyl residue (6) leads to a drop in both RBA and AI activity. A chain length of two to three carbon atoms and a pyrrolidino ring appear to be necessary for activity in these compounds. It has been found that while the trans isomers with the tertiary aminoalkoxy side chain in the para position of the 4-phenyl radical were the most active, in the corresponding cis-chromans and chromenes, analogues with this chain in the meta position were most active; the ortho substituted compounds of all these series were inactive. In 3-phenyl-substituted compounds, the trans isomer carrying the p-hydroxy substituent (33) was found to be the most active; the corresponding pyrrolidinoethyl ether (13) showed a lower order of activity. The implication of these observations on the mapping of the different subsites on the receptor has been discussed.

  DOI：

  10.1021/jm00358a026