5-chloro-N,N-diphenylhexanamide | 1334228-80-6

• 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: 5-chloro-N,N-diphenylhexanamide
• CAS: 1334228-80-6
• 化学式: C₁₈H₂₀ClNO
• 分子量: 301.816
• InChiKey: NWBHFVFJNCUVHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  5-chloro-N,N-diphenylhexanamide 、 (9-BBN)(CH2)3(p-anisyl) 在 potassium tert-butylate 、 NiBr2*diglyme 、 (1R,2R)-(+)-N,N-二甲基-1,2-二苯基-1,2-二乙胺 作用下， 以 正己醇 、 乙醚 、 正己烷 为溶剂， 反应 25.0h， 生成 (R)-8-(4-methoxyphenyl)-5-methyl-N,N-diphenyloctanamide 、 (S)-8-(4-methoxyphenyl)-5-methyl-N,N-diphenyloctanamide
  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：

  丁位己内酯 在 氯化亚砜 、 zinc(II) chloride 作用下， 以 苯 为溶剂， 反应 30.0h， 生成 5-chloro-N,N-diphenylhexanamide
  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