N-(9-fluorenylidene) α-aminoacetonitrile | 1334168-04-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-(9-fluorenylidene) α-aminoacetonitrile
• 英文别名: 2-(9H-fluoren-9-ylideneamino)acetonitrile；2-(Fluoren-9-ylideneamino)acetonitrile
• CAS: 1334168-04-5
• 化学式: C₁₅H₁₀N₂
• 分子量: 218.258
• InChiKey: KTKPRWFNEWJTLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  36.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(9-fluorenylidene) α-aminoacetonitrile 、 N-(p-methoxybenzylidene)diphenylphosphinamide 在 四甲基胍 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.5h， 以85%的产率得到syn-3-diphenylphosphinylamino-2-(9H-fluoren-9-ylideneamino)-3-(p-methoxyphenyl)propanenitrile
  参考文献：
  名称：

  Catalytic Mannich-type reactions of α-aminoacetonitrile using fluorenylidene as a protecting and activating group

  摘要：

  Catalytic Mannich-type reactions of 9-fluorenylidene-protected alpha-aminoacetonitrile with imines were investigated. The desired reactions proceeded smoothly to afford the Mannich-type adducts in high yields with high diastereoselectivities in the presence of a catalytic amount of 1,1,3,3-tetramethylguanidine (TMG). A chiral guanidine catalyzed the reaction with good enantioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.044
• 作为产物：
  描述：

  9-芴酮 在 氨 、 四氯化钛 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 N-(9-fluorenylidene) α-aminoacetonitrile
  参考文献：
  名称：

  Catalytic Mannich-type reactions of α-aminoacetonitrile using fluorenylidene as a protecting and activating group

  摘要：

  Catalytic Mannich-type reactions of 9-fluorenylidene-protected alpha-aminoacetonitrile with imines were investigated. The desired reactions proceeded smoothly to afford the Mannich-type adducts in high yields with high diastereoselectivities in the presence of a catalytic amount of 1,1,3,3-tetramethylguanidine (TMG). A chiral guanidine catalyzed the reaction with good enantioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.044

文献信息

• Catalytic Asymmetric Mannich-Type Reaction of<i>N</i>-Alkylidene-α-Aminoacetonitrile with Ketimines
  作者：Shaoquan Lin、Yuji Kawato、Naoya Kumagai、Masakatsu Shibasaki

  DOI：10.1002/anie.201412377

  日期：2015.4.20

  cooperative catalyst allows for an efficient stereoselective coupling of N‐alkylidene‐α‐aminoacetonitrile and ketimines to access this class of compounds bearing consecutive tetra‐ and trisubstituted stereogenic centers. The strategic use of a soft Lewis basic thiophosphinoyl group for ketimines is the key to promoting the reaction, and aliphatic ketimines serve as suitable substrates with as little as

  旋光邻位二胺是有机合成中通用的手性结构单元。柔软的路易斯酸/硬布朗斯台德碱协同催化剂可实现N-亚烷基-α-氨基乙腈和酮亚胺的高效立体选择性偶联，以访问带有连续四和三取代立体中心的此类化合物。酮基酮战略性地使用柔软的路易斯碱性硫代膦酰基基团是促进反应的关键，脂族酮基酮可作为合适的底物，催化剂负载量低至3 mol％。