(E)-1-氯戊-1-烯-3-酮 | 58953-12-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (E)-1-氯戊-1-烯-3-酮
• 英文名称: (E)-1-chloropent-1-en-3-one
• 英文别名: 1-chloro-1-penten-3-one；1t-chloro-pent-1-en-3-one；1t-Chlor-pent-1-en-3-on；2-Chlorovinyl ethyl ketone
• CAS: 58953-12-1
• 化学式: C₅H₇ClO
• 分子量: 118.563
• InChiKey: CFMFGANUEMXVTA-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 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-氯戊-1-烯-3-酮 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 3-羟基-戊醛二甲基缩醛
  参考文献：
  名称：

  Gruenanger; Grieco, Gazzetta Chimica Italiana, 1958, vol. 88, p. 296,305

  摘要：

  DOI：
• 作为产物：
  描述：

  氯乙烯 、 丙酰氯 在 三氯化铝 、 氯仿 作用下， 生成 (E)-1-氯戊-1-烯-3-酮
  参考文献：
  名称：

  Klimko et al., Zhurnal Obshchei Khimii, 1957, vol. 27, p. 370,273; engl. Ausg. S. 415, 417

  摘要：

  DOI：

文献信息

• Ketovinylation of β-dicarbonyl compounds
  作者：N.K. Kochetkov、L.J. Kudryashov、B.P. Gottich

  DOI：10.1016/0040-4020(61)80100-2

  日期：1961.1

  labile hydrogens results in the formation of complex mixtures. Ethyl malonate and ethyl acetoacetate have, however, been successfully ketovinylated. In the former case, α-carbethoxy-δ-keto-β,γ-unsaturated acids are produced in high yield and depending on the conditions of ketovinylation of ethyl acetoacetate either 4-alkyl salicyclic acids or polysubstituted benzene derivatives may be prepared. Further,

  通常仅用一个不稳定的氢将酮乙烯基引入β-二羰基化合物中，但是存在两个不稳定的氢会导致形成复杂的混合物。然而，丙二酸乙酯和乙酰乙酸乙酯已被成功酮化。在前一种情况下，高产率地生产α-乙氧基-δ-酮基-β，γ-不饱和酸，并且根据乙酰乙酸乙酯的酮乙烯基化的条件，可以制备4-烷基水杨酸或多取代的苯衍生物。此外，丙二酸乙酯和乙酰乙酸烷基酯的酮乙烯基化产物可用于合成（1）不饱和脂族酮酸或二酮或（2）多种α-吡喃酮衍生物。提出了乙酰乙酸乙酯的酮乙烯基化机理，并提出了反式 建立了酮乙烯基化产品的构型。
• A highly efficient synthesis of optically pure γ-iodo allylic alcohols and their conversion into various optically active allylic alcohols
  作者：Yasunori Kitano、Takashi Matsumoto、Takenori Wakasa、Sentaro Okamoto、Toshiyuki Shimazaki、Yuichi Kobayashi、Fumie Sato、Katsuaki Miyaji、Kazutaka Arai

  DOI：10.1016/s0040-4039(01)91371-1

  日期：1987.1

  Kinetic resolution of γ-iodo allylic alcohols by the Sharpless asymmetric epoxidation reaction proceeds with very large rate differences for the two enantiomers, thus providing a highly efficient method for preparation of optically pure . The alcohols thus prepared can be readily converted into various secondary allylic alcohols through the coupling reaction with nucleophiles.

  对于两种对映异构体，通过Sharpless不对称环氧化反应进行的γ-碘烯丙基醇的动力学拆分具有非常大的速率差异，从而提供了一种高效的制备光学纯的方法。通过与亲核试剂的偶联反应，可以容易地将由此制备的醇转化为各种仲烯丙基醇。
• Therapeutic agents
  申请人：Knoll Aktiengesellschaft

  公开号：US05753665A1

  公开（公告）日：1998-05-19

  Compounds of formula (I) which includes pharmaceutically acceptable salts thereof and stereoisomers thereof: ##STR1## wherein: R.sub.1 represents H or one of the following groups (optionally substituted with one or more of halo, cyano, hydroxy or amino): C.sub.1-6 alkyl, C.sub.1-6 alkoxy or C.sub.1-6 alkanoyl; R.sub.2 and R.sub.3 independently represent H or one of the following groups (optionally substituted with one or more of halo, cyano, hydroxy or amino): C.sub.1-6 alkyl, C.sub.1-6 alkoxy or C.sub.1-6 alkanoyl, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulphinyl or C.sub.1-6 alkylsulphonyl; R.sub.4 and R.sub.5 combined together with the carbon atom to which they are attached represent C.sub.3-6 cycloalkylidene (each alkyl or cycloalkylidene being optionally substituted with one or more of halo, cyano, hydroxy, amino or C.sub.1-6 alkyl); and R.sub.6, R.sub.7 and R.sub.8 independently represent H, halo, hydroxy, mercapto, cyano or one of the following groups (optionally substituted with one or more of halo, cyano, hydroxy or amino; and any nitrogen atom being optionally substituted with one or more C.sub.1-6 alkyl): C.sub.1-6 alkyl, C.sub.1-6 alkoxy or C.sub.1-6 alkanoyl, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulphinyl, etc; have utility in the treatment and/or prophylaxis or seizures, neurological disorders such as epilepsy and/or conditions in which there is neurological damage such as stroke, brain trauma, head injuries and haemorrhage.

  公式（I）的化合物包括其药用盐和立体异构体：其中：R.sub.1代表H或以下组之一（可选择地用一个或多个卤素，氰基，羟基或氨基取代）：C.sub.1-6烷基，C.sub.1-6烷氧基或C.sub.1-6酰基；R.sub.2和R.sub.3独立地代表H或以下组之一（可选择地用一个或多个卤素，氰基，羟基或氨基取代）：C.sub.1-6烷基，C.sub.1-6烷氧基或C.sub.1-6酰基，C.sub.1-6硫代烷基，C.sub.1-6磺基烷基或C.sub.1-6磺酰基；R.sub.4和R.sub.5与它们连接的碳原子一起代表C.sub.3-6环烷基亚甲基（每个烷基或环烷基亚甲基可选择地用一个或多个卤素，氰基，羟基，氨基或C.sub.1-6烷基取代）；R.sub.6，R.sub.7和R.sub.8独立地代表H，卤素，羟基，巯基，氰基或以下组之一（可选择地用一个或多个卤素，氰基，羟基或氨基取代；任何氮原子可选择地用一个或多个C.sub.1-6烷基取代）：C.sub.1-6烷基，C.sub.1-6烷氧基或C.sub.1-6酰基，C.sub.1-6硫代烷基，C.sub.1-6磺基烷基等；在治疗和/或预防癫痫发作，神经系统疾病如癫痫和/或存在神经损伤的情况下如中风，脑外伤，头部受伤和出血等方面具有用途。
• Stereospecific Synthesis of Cryptophycin 1
  作者：Lian-Hai Li、Marcus A. Tius

  DOI：10.1021/ol020001r

  日期：2002.5.1

  [reaction: see text] A brief stereospecific synthesis of cryptophycin 1 is described in which (R)-mandelic acid serves as the sole source of asymmetry for unit A. The key step is a hetero-Diels-Alder cycloaddition.

  [反应：见正文]描述了隐藻霉素1的简短立体定向合成，其中（R）-扁桃酸是单元A不对称的唯一来源。关键步骤是异Diels-Alder环加成反应。
• Efficient Trapping of Ketone Enolates With Acrylate and β-Sulfonylacrylate Thioesters, β-Sulfonyl-, β-Sulfinyl- and β-Chloro-Vinyl Ketones; Facile Preparation of a Hydrindanone, cis-Dimethyloctalone, and Unsaturated 1,5-Dicarbonyl Compounds
  作者：RJ Dancer、RK Haynes、WA Loughlin、SC Vonwiller

  DOI：10.1071/ch9901375

  日期：——

  Tandem conjugate addition-ring closure involving reaction of the lithium enolate arising from conjugate addition of lithiated (E)-but-2- enyldiphenylphosphine oxide to 2-methyl-cyclopent-2-enone with two moles of t-butylthioacrylate generates a hydrindanol, and, in the presence of copper(I), a lactone derived from the hydrindanol. β-Sulfonylacrylate phenyl and t-butyl thioesters, β-chlorovinyl, β- sulfonyl- and β-sulfinyl-vinyl ketones react with the foregoing enolate, and with the enolate generated through conjugate addition of a methylcuprate to 2-methylcyclohexenone to give unsaturated 1,5-dicarbonyl compounds. The β-chlorovinyl ketones in particular react rapidly and in high yield. 2-Methylcyclohexenone has thereby been converted into a cis-dimethyl octalone; the conversion illustrates the effectiveness of β-chlorovinyl methyl ketone in the Robinson annelation. Reactions of the lithium enolate and titanium enol of 2,6- dimethylcyclohexanone with the β-substituted enones to give the corresponding unsaturated 1,5-dicarbonyl compounds and other products are also recorded.

  串联共轭加成-环闭合反应涉及将锂化的(E)-2-丁烯基二苯氧化膦与 2-甲基-2-环戊烯酮共轭加成而生成的烯酸锂与两摩尔的硫代丙烯酸叔丁酯反应，生成氢茚醇，并在铜(I)存在下生成氢茚醇衍生的内酯。β-磺酰基丙烯酸酯苯基和 t-丁基硫代酯、β-氯乙烯基、β-磺酰基和 β-磺酰基乙烯基酮与上述烯醇发生反应，并与 2-甲基环己烯酮与甲基缩二脲共轭加成生成的烯醇发生反应，生成不饱和的 1,5-二羰基化合物。其中，β-氯乙烯酮的反应速度快，产率高。2-Methylcyclohexenone 由此转化为顺式二甲基辛酮；这一转化说明了 β-氯乙烯基甲基酮在罗宾逊环化反应中的有效性。此外，还记录了 2,6-二甲基环己酮的锂烯醇和钛烯醇与 β-取代烯酮的反应，从而得到相应的不饱和 1,5-二羰基化合物和其他产物。