4-chloro-N-methoxy-N-methylhexanamide | 1334228-81-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-chloro-N-methoxy-N-methylhexanamide
• CAS: 1334228-81-7
• 化学式: C₈H₁₆ClNO₂
• 分子量: 193.674
• InChiKey: HUGHLYQPNDZYHF-UHFFFAOYSA-N

物化性质

• 沸点：
  233.2±42.0 °C(Predicted)
• 密度：
  1.057±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-chloro-N-methoxy-N-methylhexanamide 、 9-(3-phenylpropyl)-9-borabicyclo[3.3.1]nonane 在 potassium tert-butylate 、 NiBr2*diglyme 、 (R)-8-(4-methoxyphenyl)-5-methyl-N,N-diphenyloctanamide 、 (1R,2R)-N,N'-二甲基-1,2-二苯基-1,2-乙二胺 作用下， 以 正己醇 、 乙醚 、 正己烷 为溶剂， 反应 25.0h， 生成 4-ethyl-N-methoxy-N-methyl-7-phenylheptanamide 、 4-ethyl-N-methoxy-N-methyl-7-phenylheptanamide
  参考文献：
  名称：

  Catalytic Asymmetric γ-Alkylation of Carbonyl Compounds via Stereoconvergent Suzuki Cross-Couplings

  摘要：

  With the aid of a chiral nickel catalyst, enantioselective gamma- (and delta-) alkylations of carbonyl compounds can be achieved through the coupling of gamma-haloamides with alkylboranes. In addition to primary alkyl nucleophiles, for the first time for an asymmetric cross-coupling of an unactivated alkyl electrophile, an arylmetal, a boronate ester, and a secondary (cyclopropyl) alkylmetal compound are shown to couple with significant enantioselectivity. A mechanistic study indicates that cleavage of the carbon-halogen bond of the electrophile is irreversible under the conditions for asymmetric carbon-carbon bond formation.

  DOI：

  10.1021/ja2079515
• 作为产物：
  描述：

  γ-己内酯 在 氯化亚砜 、 potassium carbonate 、 zinc(II) chloride 作用下， 以 乙醚 、 水 为溶剂， 反应 24.58h， 生成 4-chloro-N-methoxy-N-methylhexanamide
  参考文献：
  名称：

  Catalytic Asymmetric γ-Alkylation of Carbonyl Compounds via Stereoconvergent Suzuki Cross-Couplings

  摘要：

  With the aid of a chiral nickel catalyst, enantioselective gamma- (and delta-) alkylations of carbonyl compounds can be achieved through the coupling of gamma-haloamides with alkylboranes. In addition to primary alkyl nucleophiles, for the first time for an asymmetric cross-coupling of an unactivated alkyl electrophile, an arylmetal, a boronate ester, and a secondary (cyclopropyl) alkylmetal compound are shown to couple with significant enantioselectivity. A mechanistic study indicates that cleavage of the carbon-halogen bond of the electrophile is irreversible under the conditions for asymmetric carbon-carbon bond formation.

  DOI：

  10.1021/ja2079515