2,5-二甲基-2,3-二氢吡喃-6-酮 | 85287-77-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 2,5-二甲基-2,3-二氢吡喃-6-酮
• 英文名称: 3,6-dimethyl-5,6-dihydro-2-pyrone
• 英文别名: 5,6-dihydro-3,6-dimethyl-2-pyrone；3,6-Dimethyl-5,6-dihydro-2H-pyran-2-one；2,5-dimethyl-2,3-dihydropyran-6-one
• CAS: 85287-77-0
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: NBXVVKIJAKTEET-UHFFFAOYSA-N

物化性质

• 沸点：
  75-90 °C(Press: 0.6 Torr)
• 密度：
  1.007±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-二甲基-2,3-二氢吡喃-6-酮 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 (R*S*)-5-hydroxy-2-methylhexanoic acid lactone 、 (2R,5R)-trans-2-Methyl-5-hexanolide
  参考文献：
  名称：

  三乙酸内酯的氢化。木蜂（Xylocopa hirsutissima）性信息素的新合成

  摘要：

  在各种催化条件下，三乙酸内酯（Ⅰ）已被氢化成不同氧化态的内酯（Ⅱ，Ⅲ和Ⅴ）。其中一个（II）的C-甲基化是方便制备木匠蜂性信息素的关键步骤。

  DOI：

  10.1016/s0040-4039(01)85553-2
• 作为产物：
  描述：

  6-甲基-3-亚甲基-5-苯基四氢吡喃-2-酮 在 second-generation metathesis catalyst titanium(IV) isopropylate 、 戊烯 作用下， 以 氘代甲苯 为溶剂， 反应 8.0h， 以100%的产率得到2,5-二甲基-2,3-二氢吡喃-6-酮
  参考文献：
  名称：

  Cross Metathesis of α-Methylene Lactones II:  γ- and δ-Lactones

  摘要：

  The cross metathesis reactivities of alpha-methylene-gamma-butyrolactone and an alpha-methylene-delta-lactone have been investigated. alpha-Methylene-gamma-butyrolactone undergoes rapid and efficient olefin isomerization in the presence of second-generation metathesis catalysts. However, cross metathesis can be achieved with the additive 2,6-dichlorobenzoquinone. In contrast, the alpha-methylene-delta-lactone neither isomerizes nor couples under similar conditions.

  DOI：

  10.1021/ol070574+

文献信息

• High diastereofacial selectivity in the reaction of silyl enol ethers with chlorosulfides
  作者：Javed Iqbal、Alka Shukla

  DOI：10.1016/s0040-4020(01)96197-6

  日期：1991.10

  The chlorosulfides 1 or 2 react with silyl enol ethers in presence of anhydrous zinc bromide to give mainly the corresponding syn products 4 or 6 respectively. The high syn selectivity of these reaction is explained by nucleophilic addition to a Chelated Chiral thioniun ion.

  氯硫化物1或2在无水溴化锌的存在下与甲硅烷基烯醇醚反应，分别主要得到相应的合成产物4或6。这些反应的高顺式选择性可以通过向螯合的手性巯基离子的亲核加成来解释。
• Oxime sulfonates and the use thereof as latent acids
  申请人：Yamato Hitoshi

  公开号：US20100167178A1

  公开（公告）日：2010-07-01

  Compounds of the formula (I), (II) or (III), wherein R 1 is for example C 1 -C 18 alkylsulfonyl, C 1 -C 10 haloalkylsulfonyl, camphorylsulfonyl, phenyl-C 1 -C 3 alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthrylsulfonyl, phenanthrylsulfonyl or heteroarylsulfonyl, R′ 1 is for example phenylenedisulfonyl, R 2 is for example CN, C 1 -C 10 haloalkyl or C 1 -C 10 haloalkyl which is substituted by (IV); Ar 1 is for example phenyl optionally substituted by a group of formula (IV); Ar′ 1 is for example phenylene which optionally is substituted by a group of formula (IV); A 1 , A 2 and A 3 independently of each other are for example hydrogen, halogen, CN, or C 1 -C 18 alkyl; D 2 is for example a direct bond, O, (CO)O, (CO)S, SO 2 , OSO 2 or C 1 -C 18 alkylene; or A 3 and D 2 together form C 3 -C 30 cycloalkenyl; or A 2 and D 2 together with the carbon of the ethylenically unsaturated double bond to which they are attached form C 3 -C 30 cycloalkyl; D 3 and D 4 for example independently of each other are a direct bond, O, S, C 1 -C 18 alkylene or C 3 -C 30 cycloalkylene provided that at least one of the radicals R 2 , Ar 1 or Ar′ 1 comprises a group of the formula (IV); are suitable as photolatent acid donors and for the preparation of corresponding polymers to be employed in chemically amplified photoresists.

  化合物的公式为（I），（II）或（III），其中R1例如为C1-C18烷基磺酰基，C1-C10卤代烷基磺酰基，樟脑磺酰基，苯基-C1-C3烷基磺酰基，苯基磺酰基，萘基磺酰基，蒽基磺酰基，菲磺酰基或杂环芳基磺酰基，R'1例如为苯基二磺酰基，R2例如为CN，C1-C10卤代烷基或被（IV）取代的C1-C10卤代烷基；Ar1例如为苯基，可选地被公式（IV）的基团取代；Ar'1例如为苯基，可选地被公式（IV）的基团取代；A1，A2和A3独立地例如为氢，卤素，CN或C1-C18烷基；D2例如为直接键，O，（CO）O，（CO）S，SO2，OSO2或C1-C18烷基；或A3和D2一起形成C3-C30环烯基；或A2和D2与它们所附着的乙烯基双键的碳一起形成C3-C30环烷基；D3和D4例如独立地为直接键，O，S，C1-C18烷基或C3-C30环烷基，至少其中之一的基团R2，Ar1或Ar'1包含公式（IV）的基团，适用作光激发酸给体，并用于制备相应的聚合物，以用于化学增强型光刻胶。
• [EN] SULFONIUM DERIVATIVES AND THE USE THEREOF AS LATENT ACIDS<br/>[FR] DÉRIVÉS DE SULFONIUM ET LEUR UTILISATION COMME ACIDES LATENTS
  申请人：BASF SE

  公开号：WO2009150074A1

  公开（公告）日：2009-12-17

  Compounds of the formula (I), wherein R1, R2 and R3 for example are hydrogen, halogen, CN, C1-C18alkyl, C1-C10 haloalkyl, (CO)R8, (CO)OR4, or (CO)NR5R6; Y is O, S or CO; D2, D3 and D4 for example are a direct bond, O, S, NR7, CO, O(CO), (CO)O, S(CO), (CO)S, NR7(CO), (CO)NR7, SO, SO2, or OSO2, C1-C18alkylene, C3-C30cycloalkylene, C2-C12alkenylene, C4-C30cycloalkenylene, Ar1; Ar1, Ar2 and Ar3 are for example phenylene, R4, R5, R6, R7 and R8 are for example hydrogen, C3-C30cycloalkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl, phenyl-C1C3-alkyl; X- is Formulae (IA), (IB) or (IC); R10 is for example C1-C18alkyl, C1-C10haloalkyl, camphoryl, phenyl-C1-C3alkyl, C3-C30cycloalkyl; and R11, R12, R13, R14 and R15 are for example C1-C10haloalkyl; are useful as polymerizable photolatent acids.

  公式（I）的化合物，其中R1，R2和R3例如是氢，卤素，CN，C1-C18烷基，C1-C10卤代烷基，（CO）R8，（CO）OR4或（CO）NR5R6; Y是O，S或CO; D2，D3和D4例如是直接键，O，S，NR7，CO，O（CO），（CO）O，S（CO），（CO）S，NR7（CO），（CO）NR7，SO，SO2或OSO2，C1-C18烷基，C3-C30环烷基，C2-C12烯基，C4-C30环烯基，Ar1; Ar1，Ar2和Ar3例如是苯基，R4，R5，R6，R7和R8例如是氢，C3-C30环烷基，C1-C18烷基，C1-C10卤代烷基，C2-C12烯基，C4-C30环烯基，苯基-C1C3-烷基; X-是公式（IA），（IB）或（IC）; R10例如是C1-C18烷基，C1-C10卤代烷基，桉叶基，苯基-C1-C3烷基，C3-C30环烷基; R11，R12，R13，R14和R15例如是C1-C10卤代烷基; 作为可聚合光致酸的有用化合物。
• Ruthenium Carbene Complexes with <i>N</i>,<i>N</i>‘-Bis(mesityl)imidazol-2-ylidene Ligands:  RCM Catalysts of Extended Scope
  作者：Alois Fürstner、Oliver R. Thiel、Lutz Ackermann、Hans-Jörg Schanz、Steven P. Nolan

  DOI：10.1021/jo9918504

  日期：2000.4.1

  The ruthenium carbene complexes 3a,b bearing imidazol-2-ylidene ligands constitute excellent precatalysts for ring-closing metathesis (RCM) reactions allowing the formation of tri- and tetrasubstituted cycloalkenes. They also apply to annulations that are beyond the scope of the standard Grubbs carbene 1 as well as to ring-closing reactions of acrylic acid derivatives even if the resulting alpha,beta-unsaturated lactones (or lactams) are tri- or tetrasubstituted. The reactivity of 3a was found to be highly dependent on the reaction medium: particularly high reaction rates are observed in toluene, although this solvent also leads to an increased tendency of the catalyst to isomerize the double bonds of the substrates.
• O-silylated enolate phenylthialkylation: A synthesis of α,β-unsaturated 5- and 6-membered lactones.
  作者：Hassan A. Khan、Ian Paterson

  DOI：10.1016/s0040-4039(00)85578-1

  日期：1982.1