2-methyl-2-(3-butenyl)-1,3-cyclopentanedione | 166517-30-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-2-(3-butenyl)-1,3-cyclopentanedione
• 英文别名: 2-(but-3-enyl)-2-methylcyclopentane-1,3-dione；2-But-3-enyl-2-methylcyclopentane-1,3-dione
• CAS: 166517-30-2
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: VJEFJHGELOYWED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-2-(3-butenyl)-1,3-cyclopentanedione 在 三氟化硼乙醚 、 四丁基溴化铵 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到(3aα,5aβ,7aα)-3a-hydroxy-5-bromo-3a,4,5,6,7,7a-hexahydro-7a-methyl-1-indenone
  参考文献：
  名称：

  Additive and Medium Effects on Lewis Acid-Promoted Cationic .pi.-Cyclizations of Alkenyl- and Alkynylcyclopentane-1,3-diones

  摘要：

  The effects of nucleophilic additives, Lewis and Bronsted acids, and solvents on BF3.Et(2)O-promoted cationic pi-cyclizations of alkynyl- and alkenylcyclopentane-1,3-diones are reported. The rates and selectivities of alkynyl dione cyclizations were significantly effected by the addition of external nucleophiles or water, and the regioselectivity of cyclization was effected by the choice of reaction solvent. Cyclizations of alkenyl diones, which fail under standard non-nucleophilic conditions, were found to be successful in the presence of added nucleophiles or with Lewis acids other than BF3.Et(2)O. The usefulness of these cationic pi-cyclizations for producing bicyclic ring systems of various functionality was also explored.

  DOI：

  10.1021/jo00107a012
• 作为产物：
  描述：

  5-已烯-2-酮 在 三氟化硼乙醚 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 51.0h， 生成 2-methyl-2-(3-butenyl)-1,3-cyclopentanedione
  参考文献：
  名称：

  Elliott, Christine E.; Miller, David O.; Burnell, D. Jean, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, vol. 2, # 2, p. 217 - 226

  摘要：

  DOI：

文献信息

• Synthesis of a Bicyclo[2.2.1]heptane Skeleton with Two Oxy-Functionalized Bridgehead Carbons via the Diels–Alder Reaction
  作者：Kazutada Ikeuchi、Tomonari Sasage、Gen Yamada、Takahiro Suzuki、Keiji Tanino

  DOI：10.1021/acs.orglett.1c03451

  日期：2021.12.3

  We describe a synthetic method for a bicyclo[2.2.1]heptane skeleton with two oxy-functionalized bridgehead carbons. This method involves an intermolecular Diels–Alder reaction using 5,5-disubstituted 1,4-bis(silyloxy)-1,3-cyclopentadienes, the diene structure of which has never been synthesized. Furthermore, the intramolecular Diels–Alder reaction using a diene bearing a dienophile moiety at the C-5

  我们描述了一种具有两个氧官能化桥头碳的双环 [2.2.1] 庚烷骨架的合成方法。该方法涉及使用 5,5-二取代的 1,4-双（甲硅烷氧基）-1,3-环戊二烯的分子间 Diels-Alder 反应，其二烯结构从未被合成。此外，使用在 C-5 位带有亲二烯体部分的二烯的分子内 Diels-Alder 反应可以提供包含双环 [2.2.1] 庚烷骨架的三环碳骨架。新型双环[2.2.1]庚烷衍生物可用作有机合成化学的通用构件。
• CuH-Catalyzed Enantioselective Desymmetrization of Cyclic 1,3-Diketones
  作者：Vaibhav B. Patil、Sandip B. Jadhav、Jagadeesh Babu Nanubolu、Rambabu Chegondi

  DOI：10.1021/acs.orglett.2c03359

  日期：2022.11.11

  cyclopentane-1,3-diones to access cyclic 3-hydroxy ketones having an all-carbon quaternary center with high diastereoselectivity via hydrosilylation using PMHS as an inexpensive hydride source. This reaction displays high functional group tolerance including reducible alkyne, alkene, and ester groups with a broad substrate scope. The importance of chiral cyclic 3-hydroxy ketone building blocks was also demonstrated

  在此，我们报告了 CuH 催化的前手性环戊烷-1,3-二酮的不对称去对称化，使用 PMHS 作为廉价的氢化物源，通过氢化硅烷化反应获得具有全碳季中心和高非对映选择性的环状 3-羟基酮。该反应显示出高官能团耐受性，包括具有广泛底物范围的可还原炔烃、烯烃和酯基团。手性环状 3-羟基酮结构单元的重要性也通过 (-)-雌酮、毒柯烯烷 E 核心和稠合吲哚的合成得到证明。
• Elliott, Christine E.; Miller, David O.; Burnell, D. Jean, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, vol. 2, # 2, p. 217 - 226
  作者：Elliott, Christine E.、Miller, David O.、Burnell, D. Jean

  DOI：——

  日期：——
• Additive and Medium Effects on Lewis Acid-Promoted Cationic .pi.-Cyclizations of Alkenyl- and Alkynylcyclopentane-1,3-diones
  作者：Aaron Balog、Steven V. Geib、Dennis P. Curran

  DOI：10.1021/jo00107a012

  日期：1995.1

  The effects of nucleophilic additives, Lewis and Bronsted acids, and solvents on BF3.Et(2)O-promoted cationic pi-cyclizations of alkynyl- and alkenylcyclopentane-1,3-diones are reported. The rates and selectivities of alkynyl dione cyclizations were significantly effected by the addition of external nucleophiles or water, and the regioselectivity of cyclization was effected by the choice of reaction solvent. Cyclizations of alkenyl diones, which fail under standard non-nucleophilic conditions, were found to be successful in the presence of added nucleophiles or with Lewis acids other than BF3.Et(2)O. The usefulness of these cationic pi-cyclizations for producing bicyclic ring systems of various functionality was also explored.