4-((2-Chloromethyl)-phenyl)-4H-dinaphth<2,1-c:1',2'-e>azepine | 184096-74-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-((2-Chloromethyl)-phenyl)-4H-dinaphth<2,1-c:1',2'-e>azepine
• CAS: 184096-74-0
• 化学式: C₂₉H₂₂ClN
• 分子量: 419.953
• InChiKey: PGQRWVOWSPXYSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.92
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  二苯基氯化膦 、 4-((2-Chloromethyl)-phenyl)-4H-dinaphth<2,1-c:1',2'-e>azepine 在 lithium 作用下， 以 四氢呋喃 为溶剂， 以65%的产率得到4-((2-Diphenylphosphinomethyl)-phenyl)-4H-dinaphth<2,1-c:1',2'-e>azepine
  参考文献：
  名称：

  Synthesis of aminophosphines containing a chiral dinaphthoazepine entity and their use in asymmetric catalysis

  摘要：

  Three azaphospha ligands with a chiral dinaphthoazepine subunit were prepared and used in asymmetric carbon-carbon bond forming reactions. The nickel catalyzed Grignard cross coupling reaction of 1-phenylethyl magnesium chloride and vinyl bromide afforded the product in up to 47% ee. The palladium catalyzed allylic substitution of 1,3-substituted propenylacetates with dimethyl malonate and the coupling of allylacetate with methyl N-(diphenylmethylene)-glycinate resulted in asymmetric inductions of up to 97% ee and 51% ee, respectively.

  DOI：

  10.1007/bf00817258
• 作为产物：
  描述：

  [2-(3,5-Dihydro-4-aza-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-phenyl]-methanol; hydrochloride 在 氯化亚砜 作用下， 以 苯 为溶剂， 生成 4-((2-Chloromethyl)-phenyl)-4H-dinaphth<2,1-c:1',2'-e>azepine
  参考文献：
  名称：

  Synthesis of aminophosphines containing a chiral dinaphthoazepine entity and their use in asymmetric catalysis

  摘要：

  Three azaphospha ligands with a chiral dinaphthoazepine subunit were prepared and used in asymmetric carbon-carbon bond forming reactions. The nickel catalyzed Grignard cross coupling reaction of 1-phenylethyl magnesium chloride and vinyl bromide afforded the product in up to 47% ee. The palladium catalyzed allylic substitution of 1,3-substituted propenylacetates with dimethyl malonate and the coupling of allylacetate with methyl N-(diphenylmethylene)-glycinate resulted in asymmetric inductions of up to 97% ee and 51% ee, respectively.

  DOI：

  10.1007/bf00817258

文献信息

• New chiral aminophosphines and their use in asymmetric catalysis
  作者：Petra Wimmer、Michael Widhalm

  DOI：10.1016/0957-4166(95)00053-r

  日期：1995.3

  Chiral aminophosphines 4, 5 and 8 were synthesized from 1 in 34%, 57% and 42% overall yield, respectively. The new ligands were investigated with respect to their efficiency in the allylic alkylation of 1,3-diphenyl-1-acetoxy-2-propene with sodium malonate, the cross-coupling reaction of phenethylmagnesium chloride with vinyl bromide, and asymmetric hydrogenations of unsatured mono- and dicarbonic acids. The highest asymmetric inductions were observed with 4 (dimethyl 1,3-diphenyl-allyl-propandioate, 96% e.e.) and 5 (N-acetylphenylalanine, 77% e.e.; methylsuccinic acid, 56% e.e., 3-phenyl-1-butene 47% e.e.).