4-异丙基-5,6-二氢吡喃-2-酮 | 21722-33-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 4-异丙基-5,6-二氢吡喃-2-酮
• 英文名称: 4-isopropyl-5,6-dihydro-2H-pyran-2-one
• 英文别名: 4-isopropyl-5,6-dihydropyran-2-one；3-isopropyl-2-penten-5-olide；4-propan-2-yl-2,3-dihydropyran-6-one
• CAS: 21722-33-8
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: VSMZEMOUEOGREW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  4-异丙基-5,6-二氢吡喃-2-酮 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以47 mg的产率得到3-异丙基-5-戊内酯
  参考文献：
  名称：

  Synthesis of Alkyl-Substituted Six-Membered Lactones through Ring-Closing Metathesis of Homoallyl Acrylates. An Easy Route to Pyran-2-ones, Constituents of Tobacco Flavor

  摘要：

  The ring-closing metathesis (RCM) reactions of homoallylic acrylates bearing alkyl substituents on various positions of their skeleton afford the corresponding pentenolides in the presence of carbene ruthenium catalysts. For R-3 = R-4 = H, or R-3 = Me, R-4 = H, the reactions are catalyzed by complex [RuCl2(PCy3)(2)(CHPh)], while a second-generation Grubbs catalyst is required when R-3 = H and R-4 = Me, R-3 = R-4 = Me, or R-3 = i-Pr and R-4 = H. Alkyl substitution at the homoallylic carbon (R-1, R-2) increases the yield of the reaction when both the acrylic and/or homoallylic double bonds are methyl-substituted. The interaction of the catalyst with the substrate in the initiation stage involves the homoallylic double bond rather than the acrylic moiety, and the resulting alkylidene species from the first-generation Grubbs catalyst can be observed by H-1 and P-31 NMR. The racemic tobacco constituents 4-isopropyl-5,6-dihydropyran-2-one and 4-isopropyltetrahydropyran-2-one are prepared via a short reaction sequence, involving the RCM reaction as the key transformation.

  DOI：

  10.1021/jo070600h
• 作为产物：
  描述：

  3-亚甲基-4-甲基戊-1-醇 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 4-异丙基-5,6-二氢吡喃-2-酮
  参考文献：
  名称：

  Synthesis of Alkyl-Substituted Six-Membered Lactones through Ring-Closing Metathesis of Homoallyl Acrylates. An Easy Route to Pyran-2-ones, Constituents of Tobacco Flavor

  摘要：

  The ring-closing metathesis (RCM) reactions of homoallylic acrylates bearing alkyl substituents on various positions of their skeleton afford the corresponding pentenolides in the presence of carbene ruthenium catalysts. For R-3 = R-4 = H, or R-3 = Me, R-4 = H, the reactions are catalyzed by complex [RuCl2(PCy3)(2)(CHPh)], while a second-generation Grubbs catalyst is required when R-3 = H and R-4 = Me, R-3 = R-4 = Me, or R-3 = i-Pr and R-4 = H. Alkyl substitution at the homoallylic carbon (R-1, R-2) increases the yield of the reaction when both the acrylic and/or homoallylic double bonds are methyl-substituted. The interaction of the catalyst with the substrate in the initiation stage involves the homoallylic double bond rather than the acrylic moiety, and the resulting alkylidene species from the first-generation Grubbs catalyst can be observed by H-1 and P-31 NMR. The racemic tobacco constituents 4-isopropyl-5,6-dihydropyran-2-one and 4-isopropyltetrahydropyran-2-one are prepared via a short reaction sequence, involving the RCM reaction as the key transformation.

  DOI：

  10.1021/jo070600h

文献信息

• Synthesis of the Sex Pheromone of the Oleander Scale (<i>Aspidiotus nerii</i>)
  作者：Mary Montaño Castañeda、Javier Marzo Bargues、Jaime Primo、Ismael Navarro Fuertes

  DOI：10.1021/acs.joc.9b01001

  日期：2019.7.5

  A total synthesis of the oleander scale [Aspidiotus nerii (Bouche)] sex pheromone, the unique sesquiterpenoid containing a cyclobutane moiety of this class of compounds, has been developed. In order to implement this sex pheromone as a new environmentally friendly tool to manage this pest, a more cost-effective, multigram synthesis was required. This new synthetic route, having a Blaise reaction, iron-catalyzed

  已经开发出夹竹桃规模的[ Aspidiotus nerii（Bouche）]性信息素的全合成，该独特的倍半萜类化合物含有此类化合物的环丁烷部分。为了将这种性信息素作为一种新的环保工具来控制这种有害生物，需要一种更具成本效益的多谱图合成方法。这种新的合成途径具有Blaise反应，铁催化的碳-碳偶合和[2 + 2]光环加成反应作为关键步骤，可提供对4-烷基内酯的一般访问以及对目标性信息素的强大访问。 。从易于获得的化合物（如3-羟基丙腈，溴乙酸乙酯和2-乙酰基丁内酯）开始，合成序列提供了A. nerii 性信息素，中间纯化最少，九个线性步骤的总收率好。
• SUBSTITUTED VINYL AND ALKINYL CYCLOHEXENOLS AS ACTIVE AGENTS AGAINST ABIOTIC STRESS IN PLANTS
  申请人：Frackenpohl Jens

  公开号：US20140080704A1

  公开（公告）日：2014-03-20

  The invention relates to substituted vinyl- and alkynylcyclohexenols of the general formula (I) and salts thereof where the R 1 , R 2 , R 3 , R 4 , R 5 , [X—Y] and Q radicals are each as defined in the description, to processes for preparation thereof and to the use thereof for enhancing stress tolerance in plants with respect to abiotic stress, and/or for increasing plant yield.

  该发明涉及通式（I）中的取代乙烯基和炔基环己烯醇及其盐，其中R1、R2、R3、R4、R5、[X—Y]和Q基团如描述中所定义，以及其制备方法和用途，用于增强植物对非生物胁迫的抗逆性，和/或增加植物产量。
• SUBSTITUTED VINYL AND ALKYNYL CYANOCYCLOALKANOLS AND VINYL AND ALKYNYL CYANOHETEROCYCLOALKANOLS AS ACTIVE AGENTS AGAINST ABIOTIC PLANT STRESS
  申请人：BAYER CROPSCIENCE AKTIENGESELLSCHAFT

  公开号：US20170197910A1

  公开（公告）日：2017-07-13

  Substituted vinyl- and alkynylcyanocycloalkanols and vinyl- and alkynylcyanoheterocyclylalkanols of the general formula (I) or salts thereof where [X—Y], Q, R 1 , R 2 , A 1 , A 2 , V, W, m and n are each as defined in the description, processes for preparation thereof and the use thereof for enhancing stress tolerance in plants with respect to abiotic stress, and/or for increasing plant yield.

  通式（I）的取代乙烯基和炔基氰基环戊醇和乙烯基和炔基氰基杂环烷基醇或其盐，其中[X—Y]，Q，R1，R2，A1，A2，V，W，m和n均如描述中定义的那样，其制备方法以及用于增强植物对非生物胁迫的耐受性和/或增加植物产量的用途。
• Anticancer agents, perfumes or foods and drinks containing omega-hydroxyfatty acids
  申请人：——

  公开号：US20030055105A1

  公开（公告）日：2003-03-20

  The present invention relates to drugs and, particularly, to anticancer agents. More particularly, the present invention relates to an anticancer agents containing, as an active ingredient, at least one compound selected from the group consisting of &ohgr;-hydroxy fatty acids and salts or esters thereof, hydroxy oxo-fatty acids and salts or esters thereof, lactones, macrocyclic ketones, and macrocyclic diesters having specific chemical structures. With respect to the compounds described above used in the present invention, since the activities of killing cancer and inhibiting cancer metastasis are significantly high, the effects of preventing the recurrence of cancer and preventing cancer are exhibited, the cytotoxicity is significantly low, and a small dose is effective, it is possible to provide anticancer agents having significantly decreased side effects. Additionally, use in combination with known antitumor agents can further enhance the activity of inhibiting cancer metastasis. Among the anticancer agents of the present invention, &ohgr;-hydroxy fatty acids can be easily obtained in high purities by hydrolyzing lactones which are also the anticancer agents of the present invention.

  本发明涉及药物，特别是抗癌剂。更具体地说，本发明涉及一种抗癌剂，其含有至少一种从以下化合物组合中选择的活性成分，包括ω-羟基脂肪酸及其盐或酯、羟基酮脂肪酸及其盐或酯、内酯、大环酮和具有特定化学结构的大环二酯。对于本发明中所述的上述化合物，由于其杀灭癌细胞和抑制癌转移的活性显著高，具有预防癌症复发和预防癌症的效果，细胞毒性显著低，且小剂量就能发挥作用，因此能够提供具有显著降低副作用的抗癌剂。此外，与已知的抗肿瘤药物结合使用可以进一步增强抑制癌转移的活性。在本发明的抗癌剂中，ω-羟基脂肪酸可以通过水解也是本发明的抗癌剂的内酯轻松获得高纯度。
• Phenyl pyrrolidine ether tachykinin receptor antagonists
  申请人：DeVita J. Robert

  公开号：US20070043015A1

  公开（公告）日：2007-02-22

  The present invention is directed to certain phenyl pyrrolidine ether compounds which are useful as neurokinin-1 (NK-1) receptor antagonists, and inhibitors of tachykinin and in particular substance P. The invention is also concerned with pharmaceutical formulations comprising these compounds as active ingredients and the use of the compounds and their formulations in the treatment of certain disorders, including emesis, depression, and anxiety.

  本发明涉及某些苯基吡咯烷醚化合物，其作为神经激肽-1（NK-1）受体拮抗剂和快速激肽，特别是物质P的抑制剂具有用途。本发明还涉及包含这些化合物作为活性成分的制药配方以及这些化合物及其配方在治疗某些疾病，包括呕吐、抑郁和焦虑方面的应用。