(Z)-α-(1-chloropentylidene)-β-methyl-β-lactone | 627526-65-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (Z)-α-(1-chloropentylidene)-β-methyl-β-lactone
• 英文别名: (3Z)-3-(1-chloropentylidene)-4-methyloxetan-2-one
• CAS: 627526-65-2
• 化学式: C₉H₁₃ClO₂
• 分子量: 188.654
• InChiKey: VVKXCTZLTMMKQX-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  3.4-(亚甲基二氧基)苯硼酸 、 (Z)-α-(1-chloropentylidene)-β-methyl-β-lactone 在 dichloropalladium;dicyclohexyl-[2-(2,6-dimethoxyphenyl)phenyl]phosphane potassium phosphate 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以92%的产率得到(Z)-α-[1-(benzo[1.3]dioxol-5-yl)pentylidene]-β-methyl-β-lactone
  参考文献：
  名称：

  α-氯亚烷基-β-内酯和β-内酰胺与有机硼酸的高效铃木偶联反应

  摘要：

  报道了通过铃木交叉偶联反应活化（Z）-α-氯亚烷基-β-内酯和（E）-α-氯亚烷基-β-内酰胺的CCl键。烷基，杂芳族，取代的苯基和烯基硼酸可以在短时间内以优异的产率与各种α-氯亚烷基-β-内酯和β-内酰胺偶联。光学活性底物的交叉偶联反应导致光学活性化合物没有相应手性中心的外消旋化。

  DOI：

  10.1002/adsc.200600234
• 作为产物：
  描述：

  3-辛炔-2-醇 、 一氧化碳 在 palladium dichloride copper dichloride 作用下， 以 四氢呋喃 为溶剂， 30.0 ℃ 、2.03 MPa 条件下， 反应 4.0h， 以64%的产率得到(Z)-α-(1-chloropentylidene)-β-methyl-β-lactone
  参考文献：
  名称：

  Mild and Efficient Synthesis of (Z)-α-Chloroalkylidene-β-lactones via the PdCl₂-Catalyzed Cyclocarbonylation of 2-Alkynols

  摘要：

  A mild and efficient methodology involving PdCl2-catalyzed cyclocarbonylation of 2-alkynols with CuCl2 for the synthesis of (Z)-alpha-chloroalkylidene-beta-lactones was developed. Using the readily available optically active propargylic alcohols allows convenient synthesis of the corresponding (Z)-alpha-chloroalkylidene-beta-lactones with high ee values. cis-Chloropalladation was observed as the major pathway, which is unique as compared to the reported data.

  DOI：

  10.1021/ol0357245

文献信息

• Pd-catalyzed Suzuki coupling reaction of chloroalkylidene-β-lactones with LB-Phos as the ligand
  作者：Pengbin Li、Bo Lü、Chunling Fu、Shengming Ma

  DOI：10.1039/c2ob26365c

  日期：——

  In this paper, LB-Phos·HBF4 salt has been applied for the Pd-catalysed Suzuki coupling reactions of optically active (Z)-α-choroalkylidene-β-lactones. Aryl, vinyl, alkyl and heteroaromatic boronic acids may be coupled with optically active β-lactones affording corresponding optically active products highly selectively and efficiently.

  本文将LB-Phos·HBF 4盐用于Pd催化的旋光（Z）-α-氯亚烷基-β-内酯的Suzuki偶联反应。芳基，乙烯基，烷基和杂芳族硼酸可以与旋光性β-内酯偶联，从而高度选择性和有效地提供相应的旋光性产物。
• Studies on Pd(II)-Catalyzed Synthesis of (<i>Z</i>)-α-Haloalkylidene-β-lactones from Cyclocarbonylation of 2-Alkynols and the Subsequent Coupling Reactions
  作者：Shengming Ma、Bin Wu、Xuefeng Jiang、Shimin Zhao

  DOI：10.1021/jo0480038

  日期：2005.4.1

  A good regio- and stereoselectivity was observed for the PdCl2-catalyzed cyclocarbonylation of 2-alkynols with CuCl2 affording (Z)-alpha-chloroalkylidene-beta-lactons. The highly optically active (Z)-alpha-chloroalkylidene-beta-lactones could be easily prepared from the readily available optically active propargylic alcohols. The Pd(II)-catalyzed cyclocarbonylation of 2-alkynols with CuBr2 was also studied. Although the yields of (Z)-alpha-bromoalkylidene-beta-lactones were low, due to the relatively higher activity of the C-Br bond, the coupling reactions of (Z)-alpha-bromoalkylidene-beta-lactones were quite smooth to afford the corresponding products in high yields. A rationale for this reaction is discussed.
• Highly Efficient Suzuki Coupling Reaction of α-Chloroalkylidene-β-lactones and β-Lactams with Organoboronic Acids
  作者：Shengming Ma、Xuefeng Jiang、Xin Cheng、Hairong Hou

  DOI：10.1002/adsc.200600234

  日期：2006.10

  -β-lactones and (E)-α-chloroalkylidene-β-lactams via the Suzuki cross-coupling reaction is reported in this paper. Alkyl, heteroaromatic, substituted phenyl- and alkenylboronic acids can be coupled with a wide variety of α-chloroalkylidene-β-lactones and β-lactams in excellent yields within a short period of time. The cross-coupling reaction of optically active substrates leads to the optically active

  报道了通过铃木交叉偶联反应活化（Z）-α-氯亚烷基-β-内酯和（E）-α-氯亚烷基-β-内酰胺的CCl键。烷基，杂芳族，取代的苯基和烯基硼酸可以在短时间内以优异的产率与各种α-氯亚烷基-β-内酯和β-内酰胺偶联。光学活性底物的交叉偶联反应导致光学活性化合物没有相应手性中心的外消旋化。
• Mild and Efficient Synthesis of (<i>Z</i>)-α-Chloroalkylidene-β-lactones via the PdCl₂-Catalyzed Cyclocarbonylation of 2-Alkynols
  作者：Shengming Ma、Bin Wu、Shimin Zhao

  DOI：10.1021/ol0357245

  日期：2003.11.1

  A mild and efficient methodology involving PdCl2-catalyzed cyclocarbonylation of 2-alkynols with CuCl2 for the synthesis of (Z)-alpha-chloroalkylidene-beta-lactones was developed. Using the readily available optically active propargylic alcohols allows convenient synthesis of the corresponding (Z)-alpha-chloroalkylidene-beta-lactones with high ee values. cis-Chloropalladation was observed as the major pathway, which is unique as compared to the reported data.