4-氯己酰氯 | 99585-00-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 中文名称: 4-氯己酰氯
• 英文名称: 4-chlorohexanoic chloride
• 英文别名: 4-chlorohexanoyl chloride；4-Chlor-hexanoylchlorid；4-Chlorohexanoyl Chloride
• CAS: 99585-00-9
• 化学式: C₆H₁₀Cl₂O
• 分子量: 169.051
• InChiKey: NLMAMSOFICKDPA-UHFFFAOYSA-N

物化性质

• 沸点：
  207.1±13.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-氯己酰氯 在 potassium tert-butylate 作用下， 以 正己醇 、 苯 为溶剂， 反应 31.0h， 生成 4-ethyl-11-(1H-indol-1-yl)-N,N-diphenylundecanamide
  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 、 zinc(II) chloride 作用下， 反应 24.0h， 生成 4-氯己酰氯
  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

文献信息

• A Convenient Synthesis of Hypotensive (±)-Oudenone
  作者：Takashi Sakai、Kohji Iwata、Masanori Utaka、Akira Takeda

  DOI：10.1246/bcsj.60.1161

  日期：1987.3

  (±)-Oudenone, 2-(tetrahydro-5-propyl-2-furylidene)-1,3-cyclopentanedione, was conveniently synthesized by BF3-catalyzed acylation of 1,3-cyclopentanedione with 4-chloroheptanoic anhydride and subsequent cyclization with triethylamine in a 36% overall yield.

  (±)-Oudenone, 2-(tetrahydro-5-propyl-2-furylidene)-1,3-cyclopentanedione，通过 BF3 催化 1,3-环戊二酮与 4-氯庚酸酐的酰化和随后与三乙胺的环化反应方便地合成总产率为 36%。
• Smit; den Hertog, Recueil des Travaux Chimiques des Pays-Bas, 1958, vol. 77, p. 73,74,77
  作者：Smit、den Hertog

  DOI：——

  日期：——
• Proceedings of the Chemical Society. April 1959
  作者：den Hertog、Smit

  DOI：10.1039/ps9590000109

  日期：——
• Potter, Alan; Tedder, John M., Journal of the Chemical Society. Perkin transactions II, 1982, p. 1689 - 1692
  作者：Potter, Alan、Tedder, John M.

  DOI：——

  日期：——
• Catalytic Asymmetric γ-Alkylation of Carbonyl Compounds via Stereoconvergent Suzuki Cross-Couplings
  作者：Susan L. Zultanski、Gregory C. Fu

  DOI：10.1021/ja2079515

  日期：2011.10.5

  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.