2-((1,1-diphenyl-1-propen-3-yl)oxy)ethanol | 136059-34-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-((1,1-diphenyl-1-propen-3-yl)oxy)ethanol
• 英文别名: 2-((3,3-diphenylallyl)oxy)ethan-1-ol；2-(3,3-diphenyl-2-propen-1-yloxy)ethanol；2-(3,3-diphenylprop-2-enoxy)ethanol
• CAS: 136059-34-2
• 化学式: C₁₇H₁₈O₂
• 分子量: 254.329
• InChiKey: XOJZHHRRXKQGCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((1,1-diphenyl-1-propen-3-yl)oxy)ethanol 在 palladium on activated charcoal 正丁基锂 、 氢气 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 正己烷 为溶剂， 20.0 ℃ 、133.32 Pa 条件下， 反应 23.0h， 生成 1-[2-(3,3-Diphenyl-propoxy)-ethyl]-1,2,3,6-tetrahydro-pyridine-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of Novel GABA Uptake Inhibitors. 4. Bioisosteric Transformation and Successive Optimization of Known GABA Uptake Inhibitors Leading to a Series of Potent Anticonvulsant Drug Candidates

  摘要：

  By bioisosteric transformations and successive optimization of known GABA uptake inhibitors, several series of novel GABA uptake inhibitors have been prepared by different synthetic approaches. These compounds are derivatives of nipecotic acid and guvacine, substituted at the nitrogen of these amino acids by various lipophilic moieties such as diarylaminoalkoxyalkyl or diarylalkoxyalkyl. The in vitro values for inhibition of [H-3]GABA uptake in rat synaptosomes was determined for each compound, and it was found that the most potent compound from this series, (R)-1-(2-(3,3-diphenyl-1-propyloxy)ethyl)-3-piperidinecarboxylic acid hydrochloride (29), is so far the most potent parent compound inhibiting GABA uptake into synaptosomes. Structure-activity results confirm our earlier observations, that an electronegative center in the chain connecting the amino acid and diaryl moiety is very critical in order to obtain high in vitro potency. Several of the novel compounds were also evaluated for their ability in vivo to inhibit clonic seizures induced by a 15 mg/kg (ip) dose of methyl 6,7-dimethoxy-4-ethyl-beta-carboline-3-carboxylate (DMCM). Some of the compounds tested show a high in vivo potency comparable with that of the recently launched anticonvulsant product 6 ((R)-1-(4,4-bis(3-methyl-2-thienyl)-3-butenyl)-3-piperidinecarboxylic acid).

  DOI：

  10.1021/jm980492e
• 作为产物：
  描述：

  地芬尼多杂质9 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 、 溶剂黄146 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 15.0h， 生成 2-((1,1-diphenyl-1-propen-3-yl)oxy)ethanol
  参考文献：
  名称：

  锰（III）辅助的特定分子内加成

  摘要：

  对低聚亚甲基系的ω-烯基3-氧代丁酸酯和3-氧代丁酰胺进行了锰（III）介导的氧化分子内加成反应，制得了8至26个成员的二氢呋喃稠合大环内酯和大环酰胺。低聚氧杂亚甲基系链的ω-烯基3-氧代丁酸酯的类似反应也得到了二氢呋喃稠合的冠醚型大环内酯，其与苦味酸钠和钾具有相转移能力。锰（III）辅助的特定分子内加成反应可以通过ω-烯基部分与锰（III）烯醇化物的π络合来解释。 分子内加成-大环化-氧化-自由基-冠醚

  DOI：

  10.1055/s-0030-1259977

文献信息

• Method of treating filariae
  申请人：Novo Nordisk A/S

  公开号：US06174898B1

  公开（公告）日：2001-01-16

  The present invention relates to a novel method for treating a mammal suffering from filariae.

  这项发明涉及一种治疗患有丝虫病的哺乳动物的新方法。
• Heterocyclic carboxylic acids
  申请人：Novo Nordisk A/S

  公开号：US05198451A1

  公开（公告）日：1993-03-30

  Novel N-substituted azaheterocyclic carboxylic acids and esters thereof in which a substituted alkyl chain forms part of the N-substituent, the compounds thus having the general formula I ##STR1## wherein Y is ##STR2## wherein R.sup.1 and R.sup.2 independently are C.sub.3-8 cycloalkyl phenyl or thienyl all of which may be optionally substituted with halogen, trifluoromethyl, C.sub.1-16 alkyl or C.sub.1-6 alkoxy; s is 1, 2 or 3; x is --CH.sub.2 --, --O-- or ##STR3## -wherein R.sup.3 is hydrogen or C.sub.1-6 -alkyl; r is 2, 3 or 4; R.sup.4 and R.sup.5 each represents hydrogen or may together represent a bond and R.sup.6 is OH or C.sub.1-8 -alkoxy; and pharmaceutically acceptable acid addition salts are potent inhibitors of GABA uptake from the synaptic cleft.

  N-取代的杂环羧酸和其酯，其中取代的烷基链构成N-取代基的一部分，因此这些化合物具有一般式I ##STR1## 其中Y为##STR2## 其中R.sup.1和R.sup.2独立地为C.sub.3-8环烷基苯或噻吩基，所有这些基可能选择性地被卤素、三氟甲基、C.sub.1-16烷基或C.sub.1-6烷氧基取代；s为1、2或3；x为--CH.sub.2--、--O--或##STR3## -其中R.sup.3为氢或C.sub.1-6-烷基；r为2、3或4；R.sup.4和R.sup.5各代表氢或可共同代表键，R.sup.6为OH或C.sub.1-8-烷氧基；和药学上可接受的酸盐是GABA从突触间隙中摄取的有效抑制剂。
• Radical C(sp³)–H Heck-type Reaction of <i>N</i>-Alkoxybenzimidoyl Chlorides with Styrenes to Construct Alkenols
  作者：Di Fang、Yidan Zhang、Yiyun Chen

  DOI：10.1021/acs.orglett.2c00593

  日期：2022.3.18

  the first radical C(sp3)–H Heck-type reaction of aliphatic alcohols for selective δ- and ε-alkenol synthesis by photoredox catalysis. N-Alkoxybenzimidoyl chlorides are developed as novel alkoxyl radical precursors with tunable redox potentials. Various alkenols can be constructed by the inert C(sp3)–H Heck-type reaction of 4-cyano-N-alkoxybenzimidoyl chlorides with styrene derivatives under redox-neutral

  我们报告了脂肪醇的第一个自由基 C(sp 3 )-H Heck 型反应，用于通过光氧化还原催化选择性合成 δ-和 ε-烯醇。N-烷氧基苯并亚胺酰氯被开发为具有可调氧化还原电位的新型烷氧基自由基前体。在氧化还原中性条件下，4-氰基-N-烷氧基苯并亚氨基酰氯与苯乙烯衍生物发生惰性 C(sp 3 )-H Heck 型反应可以构建各种烯醇，该反应可以在克级规模上进行，并且易于衍生化.
• Synthesis of Macrocyclic Amides Using Manganese(III)- Based Intramolecular Cyclization of N-(ω-Alkenyl)-3- oxobutanamides
  作者：Yosuke Ito、Hiroshi Nishino

  DOI：10.1515/hc.2009.15.6.467

  日期：2009.1

  The temperature under an argon atmosphere resulted in the oxidative intramolecular radical cyclization that produced The reaction of N-(omega-alkenyl)-3-oxobutanamides with manganese(III) acetate in glacial acetic acid at reflux bicyclomacrocyclic amides in moderate to good yields.
• Mizuno, Kazuhiko; Tamai, Toshiyuki; Nishiyama, Toshinori, Angewandte Chemie, 1994, vol. 106, # 20, p. 2203 - 2205
  作者：Mizuno, Kazuhiko、Tamai, Toshiyuki、Nishiyama, Toshinori、Tani, Kyoko、Sawasaki, Mayumi、et al.

  DOI：——

  日期：——