2,2,3,3,3-pentafluoropropyl trichloromethanesulfonate | 123241-05-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 2,2,3,3,3-pentafluoropropyl trichloromethanesulfonate
• CAS: 123241-05-4
• 化学式: C₄H₂Cl₃F₅O₃S
• 分子量: 331.475
• InChiKey: SYRDSSOZKPGICD-UHFFFAOYSA-N

物化性质

• 沸点：
  241.3±40.0 °C(Predicted)
• 密度：
  1.806±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,2,3,3,3-pentafluoropropyl trichloromethanesulfonate 、 NORCODEINE 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 N-(2,2,3,3,3-pentafluoro-n-propyl)norcodeine
  参考文献：
  名称：

  Synthesis and structural requirements of N-substituted norapomorphines for affinity and activity at dopamine D-1, D-2, and agonist receptor sites in rat brain

  摘要：

  A series of N-substituted analogues of (R)-(-)-norapomorphine were synthesized to study the optimal structural requirements of the N-alkyl side chain to interact with D-1 and D-2 dopaminergic receptors as well as dopamine (DA) agonist binding sites. Evaluations included testing the affinity of these compounds for DA receptor sites in rat striatal tissue and assessing stereotypy as a behavioral index of dopaminergic activity. The electronic, steric, and lipophilic properties of the N-alkyl side chain were found to be related to affinity, D-2 selectivity, and dopaminergic activity. All 11 compounds evaluated had relatively low affinity at D-1 sites. Optimum D-2 and agonist-site affinity as well as agonist activity were exhibited by N-cyclopropylmethyl (7) greater than or equal to N-allyl (8) greater than or equal to N-propyl (4) or N-ethyl (3) substituted compounds. Branching of the N-alkyl side chain as in N-isopropyl (5) and N-isobutyl (6) markedly reduced the D-2 affinity and activity, presumably due to steric effects. The N-trifluoroethyl (10) and N-pentafluoropropyl (11) derivatives had low affinity for all their dopamine receptor sites and no agonistic activity; evidently, the highly electronegative F atoms decrease basicity of the N atom and therefore decrease the ability of the N atom to be cationic at physiological pH, a proposed requirement for high-affinity binding to DA receptors.

  DOI：

  10.1021/jm00163a007
• 作为产物：
  描述：

  三氯甲基磺酰氯 、 2,2,3,3,3-五氟-1-丙醇 在 sodium hydroxide 作用下， 生成 2,2,3,3,3-pentafluoropropyl trichloromethanesulfonate
  参考文献：
  名称：

  1-Poly(fluoroalkyl)benzodiazepines

  摘要：

  DOI：

  10.1021/jm00270a008

文献信息

• SHARPE, T. R.;CHERKOFSKY, S. C.;HEWES, W. E.;SMITH, D. H.;GREGORY, W. A.;+, J. MED. CHEM., 1985, 28, N 9, 1188-1194
  作者：SHARPE, T. R.、CHERKOFSKY, S. C.、HEWES, W. E.、SMITH, D. H.、GREGORY, W. A.、+

  DOI：——

  日期：——
• US6218364B1
  申请人：——

  公开号：US6218364B1

  公开（公告）日：2001-04-17
• Synthesis and structural requirements of N-substituted norapomorphines for affinity and activity at dopamine D-1, D-2, and agonist receptor sites in rat brain
  作者：Yigong Gao、Vishnu J. Ram、Alexander Campbell、Nora S. Kula、Ross J. Baldessarini、John L. Neumeyer

  DOI：10.1021/jm00163a007

  日期：1990.1

  A series of N-substituted analogues of (R)-(-)-norapomorphine were synthesized to study the optimal structural requirements of the N-alkyl side chain to interact with D-1 and D-2 dopaminergic receptors as well as dopamine (DA) agonist binding sites. Evaluations included testing the affinity of these compounds for DA receptor sites in rat striatal tissue and assessing stereotypy as a behavioral index of dopaminergic activity. The electronic, steric, and lipophilic properties of the N-alkyl side chain were found to be related to affinity, D-2 selectivity, and dopaminergic activity. All 11 compounds evaluated had relatively low affinity at D-1 sites. Optimum D-2 and agonist-site affinity as well as agonist activity were exhibited by N-cyclopropylmethyl (7) greater than or equal to N-allyl (8) greater than or equal to N-propyl (4) or N-ethyl (3) substituted compounds. Branching of the N-alkyl side chain as in N-isopropyl (5) and N-isobutyl (6) markedly reduced the D-2 affinity and activity, presumably due to steric effects. The N-trifluoroethyl (10) and N-pentafluoropropyl (11) derivatives had low affinity for all their dopamine receptor sites and no agonistic activity; evidently, the highly electronegative F atoms decrease basicity of the N atom and therefore decrease the ability of the N atom to be cationic at physiological pH, a proposed requirement for high-affinity binding to DA receptors.
• 1-Poly(fluoroalkyl)benzodiazepines
  作者：Martin Steinman、John G. Topliss、Robert Alekel、Yee-Shing Wong、Eunice E. York

  DOI：10.1021/jm00270a008

  日期：1973.12