(R)-(+)-(E)-α-(1-chloropentylidene)-β-ethyl-N-benzyl-β-lactam | 850194-70-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-(+)-(E)-α-(1-chloropentylidene)-β-ethyl-N-benzyl-β-lactam
• 英文别名: (3E,4R)-1-benzyl-3-(1-chloropentylidene)-4-ethylazetidin-2-one
• CAS: 850194-70-6
• 化学式: C₁₇H₂₂ClNO
• 分子量: 291.821
• InChiKey: PAWCGIZPJRRMDA-DPEHCCBOSA-N

物化性质

• 沸点：
  435.8±44.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-(+)-(E)-α-(1-chloropentylidene)-β-ethyl-N-benzyl-β-lactam 、 4-甲苯硼酸 在 dichloropalladium;dicyclohexyl-[2-(2,6-dimethoxyphenyl)phenyl]phosphane potassium phosphate 作用下， 以 甲苯 为溶剂， 反应 0.25h， 以91%的产率得到(R)-(E)-α-(1-p-tolylpentylidene)-β-ethyl-N-benzyl-β-lactam
  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：

  (R)-4-nonyn-3-yl acetate 在 palladium dichloride 氢氧化钾 、 三乙胺 、 对苯醌 、 copper dichloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 40.0 ℃ 、2.07 MPa 条件下， 反应 12.0h， 生成 (R)-(+)-(E)-α-(1-chloropentylidene)-β-ethyl-N-benzyl-β-lactam
  参考文献：
  名称：

  PdCl₂-Catalyzed Efficient Transformation of Propargylic Amines to (E)-α-Chloroalkylidene-β-lactams

  摘要：

  The PdCl2-catalyzed cyclocarbonylation reaction of propargylic amines with CuCl2 and benzoquinone afforded (E)-alpha-chloroalkylidene-beta-lactams in moderate to good yields. The formation of the corresponding Z-isomers or five-membered products was not observed. The reaction of the readily available optically active propargylic amines provides a convenient synthesis of the corresponding (E)-alpha-chloroalkylidene-beta-lactams with high ee values. The structure and the stereochemistry of the products were established by the X-ray single-crystal diffraction study of (E)-6d and (E)-6e, which indicates that the stereoselectivity in this reaction is different from what was observed with propargylic alcohols. A rationale for this reaction was proposed.

  DOI：

  10.1021/jo0480996

文献信息

• PdCl₂-Catalyzed Efficient Transformation of Propargylic Amines to (<i>E</i>)-α-Chloroalkylidene-β-lactams
  作者：Shengming Ma、Bin Wu、Xuefeng Jiang

  DOI：10.1021/jo0480996

  日期：2005.4.1

  The PdCl2-catalyzed cyclocarbonylation reaction of propargylic amines with CuCl2 and benzoquinone afforded (E)-alpha-chloroalkylidene-beta-lactams in moderate to good yields. The formation of the corresponding Z-isomers or five-membered products was not observed. The reaction of the readily available optically active propargylic amines provides a convenient synthesis of the corresponding (E)-alpha-chloroalkylidene-beta-lactams with high ee values. The structure and the stereochemistry of the products were established by the X-ray single-crystal diffraction study of (E)-6d and (E)-6e, which indicates that the stereoselectivity in this reaction is different from what was observed with propargylic alcohols. A rationale for this reaction was proposed.
• 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。