3-(cyclopent-2-entyl)pentane-2,4-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(cyclopent-2-entyl)pentane-2,4-dione
• 英文别名: 3-Cyclopent-2-en-1-ylpentane-2,4-dione
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: IZLMHGUULGXPDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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

• 作为产物：
  描述：

  环戊烯 、 乙酰丙酮 在 叔丁基过氧化氢 、 cobalt(II) chloride 、 copper(I) bromide 作用下， 以 癸烷 为溶剂， 以53%的产率得到3-(cyclopent-2-entyl)pentane-2,4-dione
  参考文献：
  名称：

  Catalytic Allylic Alkylation via the Cross-Dehydrogenative-Coupling Reaction between Allylic sp³ C−H and Methylenic sp³ C−H Bonds

  摘要：

  A catalytic allylic alkylation was developed via the cross-dehydrogenative-coupling reaction of allylic sp3 C-H and methylenic sp3 C-H catalyzed by copper bromide and cobalt chloride in the presence of an oxidizing reagent, t-BuOOH. This methodology provides a direct way to use allylic sp3 C-H bonds for forming C-C bonds.

  DOI：

  10.1021/ja056541b

文献信息

• PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE ALLYL COMPOUND
  申请人：Ootsuka Yoshikazu

  公开号：US20090182153A1

  公开（公告）日：2009-07-16

  To provide a novel process for producing an optically active allyl compound which is useful as an intermediate raw material for e.g. pharmaceutical products. A process for producing an optically active allyl compound of the formula (4): (wherein “*” represents an asymmetric carbon atom), which comprises reacting an allyloxy compound of the formula (1): (wherein R 1 is a C 1-6 alkyl group or a C 1-6 alkoxyl group, and each of R 2 , R 3 , R 4 , R 5 and R 6 independently is a C 1-6 alkyl group which may be linear, branched or cyclic, a hydrogen atom or a C 6-12 aromatic group, provided that R 2 and R 6 may be located in the same ring) with a hydrogenated compound of the formula (3): (wherein X is a carbon atom, an oxygen atom, a sulfur atom or a nitrogen atom, and each of R 8 , R 9 and R 10 independently is a C 1-24 alkyl group which may be linear, branched or cyclic, a C 1-24 alkylcarbonyl group which may be branched or cyclic, a C 1-24 alkoxycarbonyl group which may be branched or cyclic, a hydrogen atom, a halogen atom or a C 6-10 aromatic group, or two of R 8 , R 9 and R 10 may together form a ring containing one or two carbonyl groups), in the presence of a palladium compound and an optically active phosphine ligand of the formula (2): (wherein each of Ar 1 , Ar 2 , Ar 3 and Ar 4 independently is a C 6-10 aromatic group, and R 7 is a structure having at least one asymmetric center or axial chirality), wherein a tertiary amine of the formula (5): (wherein each of R 11 , R 12 and R 13 independently is a C 2-12 aliphatic group or a C 2-12 substituted aliphatic group, which may be linear, branched or cyclic, or a C 6-10 aromatic group or a C 6-10 substituted aromatic group) is present in the above reaction system.

  提供一种用于生产光学活性丙烯基化合物的新颖工艺，该化合物可用作制药产品的中间原料。生产光学活性丙烯基化合物的工艺如下：将式（1）的丙烯氧基化合物（其中R1是C1-6烷基或C1-6烷氧基，R2、R3、R4、R5和R6分别是C1-6烷基，可以是直链、支链或环状，氢原子或C6-12芳香基，但R2和R6可以位于同一环中）与式（3）的氢化合物反应（其中X是碳原子、氧原子、硫原子或氮原子，R8、R9和R10分别是C1-24烷基，可以是直链、支链或环状，C1-24烷基羰基，可以是支链或环状，C1-24烷氧羰基，可以是支链或环状，氢原子，卤原子或C6-10芳香基，或R8、R9和R10中的两个可以一起形成含有一个或两个羰基的环），在钯化合物和式（2）的光学活性膦配体的存在下进行，其中式（2）中的Ar1、Ar2、Ar3和Ar4分别是C6-10芳香基，R7是至少具有一个不对称中心或轴手性的结构，反应体系中还存在式（5）的三级胺（其中R11、R12和R13分别是C2-12脂肪基或C2-12取代脂肪基，可以是直链、支链或环状，或C6-10芳香基或C6-10取代芳香基）。
• Catalytic Allylic Alkylation via the Cross-Dehydrogenative-Coupling Reaction between Allylic sp³ C−H and Methylenic sp³ C−H Bonds
  作者：Zhiping Li、Chao-Jun Li

  DOI：10.1021/ja056541b

  日期：2006.1.1

  A catalytic allylic alkylation was developed via the cross-dehydrogenative-coupling reaction of allylic sp3 C-H and methylenic sp3 C-H catalyzed by copper bromide and cobalt chloride in the presence of an oxidizing reagent, t-BuOOH. This methodology provides a direct way to use allylic sp3 C-H bonds for forming C-C bonds.