(E)-1-phenyldec-4-en-3-one | 145822-78-2

• 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: (E)-1-phenyldec-4-en-3-one
• 英文别名: 1-Phenyl-4-decen-3-one
• CAS: 145822-78-2
• 化学式: C₁₆H₂₂O
• 分子量: 230.35
• InChiKey: PELOEOMCQKLYQI-FMIVXFBMSA-N

物化性质

• 沸点：
  348.8±21.0 °C(Predicted)
• 密度：
  0.940±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-phenyldec-4-en-3-one 在 sodium ethanolate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 48.0h， 生成 (1R,2S,3R)-2-Pentyl-3-(3-phenyl-propionyl)-cyclopropanecarboxylic acid ethyl ester
  参考文献：
  名称：

  在DBU存在下用乙基二甲基s乙酸溴化铵对烯类进行立体选择性环丙烷化

  摘要：

  α的环丙烷化反应，β不饱和酮1A-1C用乙酸乙酯（二甲基sulfuranylidene）乙酸酯（EDSA），产生在原位由相应的锍溴化物盐和1,8-二氮杂双环[5,4,0]十一碳-7-甲苯中的烯烃（DBU）仅导致外加合物2a-c（de = 100％）。无环烯酮1d-g主要产生具有高度立体控制度的“反式”环丙烷4d-g（3 3 80％）。将溶剂改变为CHCl 3分别得到“反式”和“顺式”环丙烷4d-g和5d-g的2：1混合物。“顺式”异构体5d-g在基本条件下可以被异构化为替代的“反式”异构体6d-g。

  DOI：

  10.1016/s0040-4039(97)00265-7
• 作为产物：
  描述：

  在 硫酸 、 silica gel 、 caesium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 74.0h， 生成 (E)-1-phenyldec-4-en-3-one
  参考文献：
  名称：

  Synthesis of α,β-Unsaturated Ketones Using Allylidenetriphenylphosphorane as a Three-carbon Unit

  摘要：

  在碱存在下，3-烷氧羰基-2-乙氧基-2-亚丙烯基三苯基膦通过一锅程序依次与烷基卤化物和醛发生反应，生成中等至高产率的共轭烯醇醚。共轭烯醇醚的水解和随后的脱羧反应提供了一种获得 α、β-不饱和酮的新途径。

  DOI：

  10.1246/cl.1992.2253

文献信息

• Reductive Halogenation Reactions: Selective Synthesis of Unsymmetrical α-Haloketones
  作者：Zhiqi Lao、Huimiao Zhang、Patrick H. Toy

  DOI：10.1021/acs.orglett.9b02324

  日期：2019.10.18

  A method for the selective synthesis of unsymmetrical α-haloketones has been developed. The key transformation is a triphenylphosphine oxide catalyzed reductive halogenation of an α,β-unsaturated ketone in which trichlorosilane is the reducing reagent and an N-halosuccinimide is the electrophilic halogen source. This method allows for a halogen atom to be installed selectively at either of two very

  已经开发出选择性合成不对称α-卤代酮的方法。关键的转变是三苯膦氧化物催化的α，β-不饱和酮的还原卤化反应，其中三氯硅烷是还原剂，N-卤代琥珀酰亚胺是亲电卤素源。该方法允许将卤素原子选择性地安装在与酮基相邻的两个非常相似取代的位点中的任一个上。
• Cyclopropyl glycine derivatives with pharmaceutical properties
  申请人：LILLY S.A.

  公开号：EP0870760A1

  公开（公告）日：1998-10-14

  A pharmaceutical compound of the formula in which R1 is C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, C3-10 cycloalkyl, C3-10 cycloalkyl-C1-10 alkyl, C3-10 cycloalkyl-C2-10 alkenyl, C3-10 cycloalky-C2-10 alkynyl, optionally substituted phenyl-C1-10 alkyl, optionally substituted phenyl-C2-10 alkenyl, optionally substituted phenyl-C2-10 alkynyl, optionally substituted naphthyl, optionally substituted naphthyl-C1-10 alkyl, C1-10 alkoxy-C1-10 alkyl, C3-10 cycloalkoxy-C1-10 alkyl, optionally substituted heterocyclyl, optionally substituted heterocyclyl-C1-10 alkyl, optionally substituted phenyl fused to C5-10 cycloalkyl, optionally substituted tricyclic, optionally substituted tricyclic-C1-10 alkyl, or [optionally substituted phenyl(CH2)n]2-C1-10 alkyl, where n is 0 or 1 to 4, and R2 is hydrogen or one of the values for R1; or a salt or ester thereof.

  一种药物化合物，其式如下 其中 R1 是 C1-10 烷基、C2-10 烯基、C2-10 炔基、C3-10 环烷基、C3-10 环烷基-C1-10 烷基、C3-10 环烷基-C2-10 烯基、C3-10 环烷基-C2-10 炔基、任选取代的苯基-C1-10 烷基、任选取代的苯基-C2-10 烯基、任选取代的苯基-C2-10 炔基、任选取代的萘基、任选取代的萘基-C1-10 烷基、C1-10烷氧基-C1-10烷基，C3-10环烷氧基-C1-10烷基，任选取代的杂环基，任选取代的杂环基-C1-10烷基，与C5-10环烷基融合的任选取代的苯基，任选取代的三环基，任选取代的三环基-C1-10烷基，或[任选取代的苯基（CH2）n]2-C1-10烷基，其中 n 为 0 或 1 至 4，且 R2 是氢或 R1 的值之一； 或其盐或酯。
• 2,3′-disubstituted-2-(2′-carboxycyclopropyl)glycines as potent and selective antagonists of metabotropic glutamate receptors
  作者：Iván Collado、Jesús Ezquerra、Angel Mazón、Concepción Pedregal、Belén Yruretagoyena、Anne E. Kingston、Rosemary Tomlinson、Rebecca A. Wright、Bryan G. Johnson、Darryle D. Schoepp

  DOI：10.1016/s0960-894x(98)00510-1

  日期：1998.10

  2-(9-Xanthylmethyl)-2-(2' -carboxycyclopropyl) glycine 6e is a novel metabotropic glutamate receptor antagonist. A series of alpha, C-3' disubstituted (carboxycyclopropyl)glycines 6f-n were prepared. Antagonist activity was observed for all these compounds at group 2 and group 3 mGluRs. Although they were slightly less active on group 2 mGluRs than non C-3' substituted 6e, the compounds 6f-n were more selective with lesser or no activity on group I mGluR subtypes (IC50 values greater than 100 mu m). (C) 1998 Elsevier Science Ltd. All rights reserved.
• Allylidenetriphenylphosphorane as a bifunctional reagent: synthesis of cyclopentenones and .alpha.,.beta.-unsaturated ketones with [3-(alkoxycarbonyl)-2-ethoxy-2-propenylidene]triphenylphosphorane
  作者：Minoru Hatanaka、Yuichiro Himeda、Ritsuo Imashiro、Yasuhiro Tanaka、Ikuo Ueda

  DOI：10.1021/jo00080a019

  日期：1994.1

  When (3-(ethoxycarbonyl)-2-ethoxy-2-propenylidene) triphenylphosphorane (6) was allowed to react with cu-bromo ketones 8a-d in dichloromethane in the presence of Cs2CO3 at room temperature, a [3 + 2] annulation occurred and led to the formation of the corresponding 2-ethoxycyclopentadienes 9a-d in excellent yields. Similarly, bromo thioester 8g underwent the annulation to give 4-(ethylthio)-cyclopentadiene 9g. Secondary bromides 2-bromo-3-pentanone and 2-bromocyclohexanone also afforded tetrasubstituted cyclopentadienes 9e and 9f in moderate yields when 2 equiv of 6 was used. The annulation is believed to proceed through a sequence involving a stepwise alkylation at the gamma position of 6 and an intramolecular Wittig reaction because of the fact that intermediate 11 was isolated. The resulting 2-ethoxycyclopentadienes 9a-g were converted quantitatively into the corresponding cyclopentenones 10a-g upon mild acid treatment. Furthermore, allylidenetriphenylphosphorane underwent a carbon elongation at both ends of the three-carbon unit via an alkylation-Wittig reaction sequence. (3-(tert-Butoxycarbonyl)-2-ethoxy-2-propenylidene)triphenylphosphorane (7) reacted first with alkyl halides and then with aldehydes in the presence of Cs2CO3 to give enol ethers 23a-f, which were converted into alpha,beta-unsaturated ketones 20, 21, and 25c-f by hydrolysis of the enol ether and then decarboxylation. In this way, shogaol (29), the pungent principle component of ginger, was conveniently synthesized starting from 2-methoxy-4-methylphenol.
• US6172058B1
  申请人：——

  公开号：US6172058B1

  公开（公告）日：2001-01-09