trans-2,2-dimethyl-3-phenyl-4-[p-(β-pyrrolidinoethoxy)phenyl]-7-hydroxychroman | 84394-36-5

• 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: trans-2,2-dimethyl-3-phenyl-4-[p-(β-pyrrolidinoethoxy)phenyl]-7-hydroxychroman
• 英文别名: 2H-1-Benzopyran-7-ol, 3,4-dihydro-2,2-dimethyl-3-phenyl-4-(4-(2-(1-pyrrolidinyl)ethoxy)-phenyl)-, (E)-；(3R,4R)-2,2-dimethyl-3-phenyl-4-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-3,4-dihydrochromen-7-ol
• CAS: 84394-36-5
• 化学式: C₂₉H₃₃NO₃
• 分子量: 443.586
• InChiKey: PAIABUZDHNKOIL-IZLXSDGUSA-N

物化性质

• 熔点：
  294-296 °C
• 沸点：
  569.0±50.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-2,2-dimethyl-3-phenyl-4-[p-(β-pyrrolidinoethoxy)phenyl]-7-hydroxychroman 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 甲醇 、 水 为溶剂， 反应 20.5h， 生成 3,4-trans-2,2-dimethyl-3-phenyl-4-(p-pyrrolidinoethoxyphenyl)-7-carboxymethoxychroman
  参考文献：
  名称：

  Srivastava, Apurva K.; Gupta, R. C.; Grover, P. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 6, p. 540 - 543

  摘要：

  DOI：
• 作为产物：
  描述：

  左美洛昔芬 在 氢氧化钾 、 一水合肼 作用下， 以 二乙二醇 为溶剂， 反应 0.5h， 以25%的产率得到trans-2,2-dimethyl-3-phenyl-4-[p-(β-pyrrolidinoethoxy)phenyl]-7-hydroxychroman
  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

文献信息

• SALMAN, MD.;RAY, SUPRABHAT;AGARWAL, A. K.;DURANI, S.;SETTY, B. S.;KAMBOJ,+, J. MED. CHEM., 1983, 26, N 4, 592-595
  作者：SALMAN, MD.、RAY, SUPRABHAT、AGARWAL, A. K.、DURANI, S.、SETTY, B. S.、KAMBOJ,+

  DOI：——

  日期：——
• Srivastava, Apurva K.; Lal, J.; Gupta, R. C., Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1994, vol. 33, # 8, p. 773 - 774
  作者：Srivastava, Apurva K.、Lal, J.、Gupta, R. C.、Grover, P. K.

  DOI：——

  日期：——
• Antifertility agents. 38. Effect of the side chain and its position on the activity of 3,4-diarylchromans
  作者：M. Salman、Suprabhat Ray、A. K. Agarwal、S. Durani、B. S. Setty、V. P. Kamboj、N. Anand

  DOI：10.1021/jm00358a026

  日期：1983.4

  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.
• Srivastava, Apurva K.; Gupta, R. C.; Grover, P. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 6, p. 540 - 543
  作者：Srivastava, Apurva K.、Gupta, R. C.、Grover, P. K.

  DOI：——

  日期：——