N-Benzyl-N-<(trifluoromethyl)sulfonyl>-3-chloropropylamine | 182014-29-5

• 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: N-Benzyl-N-<(trifluoromethyl)sulfonyl>-3-chloropropylamine
• 英文别名: 3-(N-benzyl-N-(trifluoromethyl)sulfonamido)propyl chloride；N-benzyl-N-(3-chloropropyl)-1,1,1-trifluoromethanesulfonamide
• CAS: 182014-29-5
• 化学式: C₁₁H₁₃ClF₃NO₂S
• 分子量: 315.744
• InChiKey: UBMBYVFCAQTMNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-Benzyl-N-<(trifluoromethyl)sulfonyl>-3-chloropropylamine 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 48.0h， 生成 N-Benzyl-N-<(trifluoromethyl)sulfonyl>-3-iodopropylamine
  参考文献：
  名称：

  Catalytic Asymmetric Addition of Polyfunctional Dialkylzincs to .beta.-Stannylated and .beta.-Silylated Unsaturated Aldehydes

  摘要：

  The addition of functionalized dialkylzincs to readily available beta-stannylated or beta-silylated unsaturated aldehydes in the presence of a catalytic amount of (1R,2R)-1,2-bis(trifluorosulfonamido)cyclohexane (8 mol%) provides chiral allylic alcohols in good yields (60-90%) and excellent enantioselectivity (usually in the range of 85-95% ee). The synthetic utility of these allylic alcohols as chiral building blacks is demonstrated. The gamma-stannylated allylic alcohols were submitted to a Stille coupling leading to polyfunctional allylic alcohols and gamma-alkoxy enones. A treatment with CuCN in N-methylpyrrolidone at 130 degrees C provided chiral unsaturated gamma-hydroxy nitriles. Finally, the desilylation of the gamma-silylated alcohols gave chiral allylic alcohols having a terminal double bond. The catalytic asymmetric addition was found to show an important inverse temperature dependance. A mechanism for this addition is proposed.

  DOI：

  10.1021/jo00094a027
• 作为产物：
  描述：

  N-<(Trifluoromethyl)sulfonyl>-3-chloropropylamine 、 溴甲苯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 N-Benzyl-N-<(trifluoromethyl)sulfonyl>-3-chloropropylamine
  参考文献：
  名称：

  Catalytic Asymmetric Addition of Polyfunctional Dialkylzincs to .beta.-Stannylated and .beta.-Silylated Unsaturated Aldehydes

  摘要：

  The addition of functionalized dialkylzincs to readily available beta-stannylated or beta-silylated unsaturated aldehydes in the presence of a catalytic amount of (1R,2R)-1,2-bis(trifluorosulfonamido)cyclohexane (8 mol%) provides chiral allylic alcohols in good yields (60-90%) and excellent enantioselectivity (usually in the range of 85-95% ee). The synthetic utility of these allylic alcohols as chiral building blacks is demonstrated. The gamma-stannylated allylic alcohols were submitted to a Stille coupling leading to polyfunctional allylic alcohols and gamma-alkoxy enones. A treatment with CuCN in N-methylpyrrolidone at 130 degrees C provided chiral unsaturated gamma-hydroxy nitriles. Finally, the desilylation of the gamma-silylated alcohols gave chiral allylic alcohols having a terminal double bond. The catalytic asymmetric addition was found to show an important inverse temperature dependance. A mechanism for this addition is proposed.

  DOI：

  10.1021/jo00094a027

文献信息

• Nickel-Catalyzed Preparations of Functionalized Organozincs
  作者：Stephan Vettel、Andrea Vaupel、Paul Knochel

  DOI：10.1021/jo960808v

  日期：1996.1.1

  (X = Br, Cl) via a halogen-zinc exchange reaction. The treatment of terminal alkenes with diethylzinc (neat, 25-60 degrees C) in the presence of Ni(acac)(2) as a catalyst (1-5 mol %) and 1,5-cyclooctadiene (COD) affords the corresponding dialkylzincs via a hydrozincation reaction. Whereas the conversion for simple alkenes bearing a remote functionality reaches 40 to 63%, the hydrozincation of allylic

  在Ni（acac）（2）（5 mol％）存在下，伯烷基溴化物或氯化物与二乙基锌的反应通过卤素-锌交换反应提供了相应的烷基卤化锌（X = Br，Cl）。在Ni（acac）（2）作为催化剂（1-5 mol％）和1,5-环辛二烯（COD）的存在下用二乙基锌（纯净的25-60摄氏度）处理末端烯烃。得到相应的二烷基锌通过氢化锌反应。带有少量官能团的简单烯烃的转化率达到40％到63％，而烯丙基，均烯丙基醇和烯丙基胺的加氢锌反应非常有效（转化率为85-95％）。用CuCN.2LiCl进行金属转移后，所有获得的有机金属锌与各种亲电试剂（烯丙基卤，烯酮，酰氯，炔基卤，丙酸乙酯）反应。
• Ostwald Roswitha, Chavant Pierre-Yves, Stadtmueller Heinz, Knochel Paul, J. Org. Chem., 59 (1994) N 15, S 4143-4153
  作者：Ostwald Roswitha, Chavant Pierre-Yves, Stadtmueller Heinz, Knochel Paul

  DOI：——

  日期：——