1-[4-(1-naphthalenylsulfonyl)phenyl]hydrazine | 881210-46-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[4-(1-naphthalenylsulfonyl)phenyl]hydrazine
• 英文别名: [4-(Naphthalene-1-sulfonyl)phenyl]hydrazine；(4-naphthalen-1-ylsulfonylphenyl)hydrazine
• CAS: 881210-46-4
• 化学式: C₁₆H₁₄N₂O₂S
• 分子量: 298.365
• InChiKey: OATHUOCHZIIWNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-氯-2-戊酮 、 1-[4-(1-naphthalenylsulfonyl)phenyl]hydrazine 以 乙醇 、 水 为溶剂， 反应 96.0h， 以84%的产率得到2-methyl-5-(1-naphthalenylsulfonyl)-1H-indole-3-ethanamine monohydrochloride
  参考文献：
  名称：

  Isomerization-Free Sulfonylation and Its Application in the Synthesis of PHA-565272A

  摘要：

  FeCl3 catalyzed an isomerization-free Friedel-Crafts sulfonylation between 1-naphthalenesulfonyl chloride and halobenzenes. The coupled halide was then displaced using 35% hydrazine in DMSO to provide the Fischer indole precursor. Pure 5-chloro-2-pentanone was the key for a successful Grandberg modification of Fischer indole synthesis that effectively constructed both the indole core and side chain of the target molecule. The development of these methods enabled a rapid preparation of kilogram quantities of PHA-565272A.

  DOI：

  10.1021/op050208a
• 作为产物：
  描述：

  1-奈硫酚 在 盐酸 、 Oxone 、 5% rhodium-on-charcoal 、 氢气 、 potassium carbonate 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 生成 1-[4-(1-naphthalenylsulfonyl)phenyl]hydrazine
  参考文献：
  名称：

  Isomerization-Free Sulfonylation and Its Application in the Synthesis of PHA-565272A

  摘要：

  FeCl3 catalyzed an isomerization-free Friedel-Crafts sulfonylation between 1-naphthalenesulfonyl chloride and halobenzenes. The coupled halide was then displaced using 35% hydrazine in DMSO to provide the Fischer indole precursor. Pure 5-chloro-2-pentanone was the key for a successful Grandberg modification of Fischer indole synthesis that effectively constructed both the indole core and side chain of the target molecule. The development of these methods enabled a rapid preparation of kilogram quantities of PHA-565272A.

  DOI：

  10.1021/op050208a

文献信息

• Isomerization-Free Sulfonylation and Its Application in the Synthesis of PHA-565272A
  作者：Thomas J. Fleck、Jiong Jack Chen、Cuong V. Lu、Kari J. Hanson

  DOI：10.1021/op050208a

  日期：2006.3.1

  FeCl3 catalyzed an isomerization-free Friedel-Crafts sulfonylation between 1-naphthalenesulfonyl chloride and halobenzenes. The coupled halide was then displaced using 35% hydrazine in DMSO to provide the Fischer indole precursor. Pure 5-chloro-2-pentanone was the key for a successful Grandberg modification of Fischer indole synthesis that effectively constructed both the indole core and side chain of the target molecule. The development of these methods enabled a rapid preparation of kilogram quantities of PHA-565272A.