N-[4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl)phenyl]pivalamide | 177530-96-0

• 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-[4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl)phenyl]pivalamide
• 英文别名: N-[4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl)phenyl]-2,2-dimethylpropanamide
• CAS: 177530-96-0
• 化学式: C₁₈H₁₉ClF₃NO₂
• 分子量: 373.803
• InChiKey: OEPQYFZNULCLRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  环丙乙炔 、 N-[4-氯-2-(2,2,2-三氟乙酰基)苯基]-2,2-二甲基丙酰胺 在 chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I) 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 3.33h， 以84%的产率得到N-[4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl)phenyl]pivalamide
  参考文献：
  名称：

  铜（I）/ N-杂环卡宾（NHC）催化的末端炔烃向三氟甲基酮的加成反应，用于连续反应器中

  摘要：

  AbstractA copper(I)/N‐heterocyclic carbene complex‐catalyzed addition of terminal alkynes to trifluoromethyl ketones at low loading is described. The developed process functions well using a range of terminal alkynes but functions best when an aryl trifluoromethyl ketone is used. This substrate scope is well‐suited for the production of active pharmaceutical ingredients (APIs) such as efavirenz. In this vein, we demonstrate that the described method can be translated into a flow process laying the framework for a completely continuous synthesis of efavirenz in the future.magnified image

  DOI：

  10.1002/adsc.201300802

文献信息

• Autocatalytic Process for the Synthesis of Chiral Propargylic Alcohols
  申请人：Chinkov Nicka

  公开号：US20120029237A1

  公开（公告）日：2012-02-02

  An autocatalytic process for the synthesis of chiral propargylic alcohols.

  手性丙炔醇的自催化合成过程。
• Copper(I)/N‐Heterocyclic Carbene (NHC)‐Catalyzed Addition of Terminal Alkynes to Trifluoromethyl Ketones for Use in Continuous Reactors
  作者：Camille A. Correia、D. Tyler McQuade、Peter H. Seeberger

  DOI：10.1002/adsc.201300802

  日期：2013.12.16

  AbstractA copper(I)/N‐heterocyclic carbene complex‐catalyzed addition of terminal alkynes to trifluoromethyl ketones at low loading is described. The developed process functions well using a range of terminal alkynes but functions best when an aryl trifluoromethyl ketone is used. This substrate scope is well‐suited for the production of active pharmaceutical ingredients (APIs) such as efavirenz. In this vein, we demonstrate that the described method can be translated into a flow process laying the framework for a completely continuous synthesis of efavirenz in the future.magnified image