丙酮-d6氰醇-d1 | 645411-28-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 丙酮-d6氰醇-d1
• 英文名称: 2-(hydroxy-d1)-2-(methyl-d3)-propanenitrile-3,3,3-d3
• 英文别名: acetone cyanohydrin-d7；acetone cyanohydrin；acetone-d6 cyanohydrin-d1；Acetoncyanhydrin-d(7)；3,3,3-Trideuterio-2-deuteriooxy-2-(trideuteriomethyl)propanenitrile
• CAS: 645411-28-5
• 化学式: C₄H₇NO
• 分子量: 92.0501
• InChiKey: MWFMGBPGAXYFAR-NWOXSKRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丙酮-d6氰醇-d1 在 硫酸 、 phosphorus pentoxide 、 对苯二酚 、 水 作用下， 反应 3.75h， 以21.5%的产率得到甲基丙烯酸-d5
  参考文献：
  名称：

  Partial Deuterium Labeling of Dimethacrylate Monomers

  摘要：

  Methacrylic acid-d(5) was prepared in a yield of 30% with 98.6% deuterium incorporation using a two step synthesis. A solution of acetone-d(6) and KCN in D2O was treated with glacial acetic acid to give the cyanohydrin of acetone-d(6). The latter compound was then dehydrated in anhydrous sulfuric acid at 120 degrees C and subsequently hydrolysed in water at 90 degrees C to form methacrylic acid-d(5). Hydrolysis of commercial nonaethyleneglycol dimethacrylate gave a mixture of ethylene glycols. These glycols were combined with methacrylic acid-d(5) in the presence of p-TsOH in benzene to form nonaethyleneglycol dimethacrylate-d(10) with similar to 21% deuterium incorporation. Deuterated bisGMA was also prepared from methacrylic acid-d(5) and diglycidyl ether of bisphenol-A.

  DOI：

  10.1007/s00706-005-0453-1
• 作为产物：
  描述：

  氘代丙酮 、 氰化钾 在 溶剂黄146 作用下， 以 重水 为溶剂， 反应 1.0h， 生成 丙酮-d6氰醇-d1
  参考文献：
  名称：

  Partial Deuterium Labeling of Dimethacrylate Monomers

  摘要：

  Methacrylic acid-d(5) was prepared in a yield of 30% with 98.6% deuterium incorporation using a two step synthesis. A solution of acetone-d(6) and KCN in D2O was treated with glacial acetic acid to give the cyanohydrin of acetone-d(6). The latter compound was then dehydrated in anhydrous sulfuric acid at 120 degrees C and subsequently hydrolysed in water at 90 degrees C to form methacrylic acid-d(5). Hydrolysis of commercial nonaethyleneglycol dimethacrylate gave a mixture of ethylene glycols. These glycols were combined with methacrylic acid-d(5) in the presence of p-TsOH in benzene to form nonaethyleneglycol dimethacrylate-d(10) with similar to 21% deuterium incorporation. Deuterated bisGMA was also prepared from methacrylic acid-d(5) and diglycidyl ether of bisphenol-A.

  DOI：

  10.1007/s00706-005-0453-1

文献信息

• Nickel-Catalyzed Isomerization/Allylic Cyanation of Alkenyl Alcohols
  作者：Ying Ding、Jinguo Long、Feilong Sun、Xianjie Fang

  DOI：10.1021/acs.orglett.1c02143

  日期：2021.8.6

  Herein reported is a nickel-catalyzed isomerization/allylic cyanation of alkenyl alcohols, which complements current methods for the allylic substitution reactions. The specific diphosphite ligand and methanol as the solvent are crucial for the success for this transformation. A gram-scale regioconvergent experiment and formal synthesis of quebrachamine demonstrate the high potential of this methodology

  本文报道了烯醇的镍催化异构化/烯丙基氰化，它补充了当前用于烯丙基取代反应的方法。特定的二亚磷酸酯配体和作为溶剂的甲醇对于这种转化的成功至关重要。克级区域会聚实验和 quebrachamine 的正式合成证明了这种方法的巨大潜力。
• Nickel-Catalyzed Asymmetric Hydrocyanation of Allenes
  作者：Jinguo Long、Jihui Gao、Xianjie Fang

  DOI：10.1021/acs.orglett.9b03938

  日期：2020.1.17

  The first catalytic enantioselective hydrocyanation of allenes catalyzed by a (R,R)-Ph-BPE-Ni(0) complex catalyst has been accomplished. Numerous optically active allylic nitriles were obtained in good yield with excellent enantioselectivities (up to 98% ee).

  由（R，R）-Ph-BPE-Ni（0）络合物催化剂催化的丙二烯的第一催化对映选择性氢氰化反应已经完成。以良好的收率和优异的对映选择性（高达98％ee）获得了许多旋光性烯丙基腈。
• Enantioselective Nickel‐Catalyzed Migratory Hydrocyanation of Nonconjugated Dienes
  作者：Rongrong Yu、Shanmugam Rajasekar、Xianjie Fang

  DOI：10.1002/anie.202008854

  日期：2020.11.23

  Metal‐catalyzed chain‐walking reactions have recently emerged as a powerful strategy to functionalize remote positions in organic molecules. However, a chain‐walking protocol for nonconjugated dienes remains scarcely reported, and developments are currently ongoing. In this Communication, a nickel‐catalyzed asymmetric hydrocyanation of nonconjugated dienes involving a chain‐walking process is demonstrated

  金属催化的链走反应最近成为一种功能强大的策略，可以使有机分子中的远端位置功能化。然而，很少有关于非共轭二烯的链走协议的报道，并且目前正在进行开发。在本交流中，展示了涉及链行走过程的非共轭二烯的镍催化不对称氢氰化。该反应显示出极好的区域选择性和化学选择性，并且可以耐受多种底物，从而以高收率和对映选择性提供产物。氘标记实验支持链步过程，该过程涉及迭代的β-H消除和重新插入过程。克级合成，区域收敛实验，
• Regio-, Chemo-, and Enantioselective Ni-Catalyzed Hydrocyanation of 1,3-Dienes
  作者：Rongrong Yu、Yidan Xing、Xianjie Fang

  DOI：10.1021/acs.orglett.0c04133

  日期：2021.2.5

  A regio-, chemo-, and enantioselective nickel-catalyzed hydrocyanation of 1,3-dienes is reported. The key to the success of this asymmetric transformation is the use of a specific multichiral diphosphite ligand. In addition to aryl-substituted 1,3-dienes, highly challenging aliphatic 1,3-diene substrates can also be preferentially converted to the corresponding 1,2-adducts in decent yields with the

  据报道1，3-二烯的区域，化学和对映选择性镍催化的氢氰化作用。这种不对称转化成功的关键是使用特定的多手性二亚磷酸酯配体。除了芳基取代的1，3-二烯以外，高挑战性的脂肪族1，3-二烯底物还可以优先地转化为具有迄今为止最高对映选择性的得体的产率的相应1，2-加合物。
• Living polymerization of methacrylic esters with aluminium porphyrin initiators. Axial ligand exchange activities of alkyl- and enolate-aluminium porphyrins in relation to the polymerization Mechanism
  作者：Takuzo Aida、Hiroshi Sugimoto、Masakatsu Kuroki、Shohei Inoue

  DOI：10.1002/poc.610080408

  日期：1995.4

  Polymerization of methacrylic esters such as benzyl methacrylate using as initiator an-equimolar mixture of methylaluminium 5,10,15,20-tetraphenylporphine [(TPP)AlMe] and 2,7,12,17-tetramethyl-3,8,13,18-tetramethylporphine [(EtioP)AlMe] proceeded from both initiators, affording a unimodal polymer of narrow molecular weight distribution, although the reactivities of (TPP)AlMe and (EtioP)AlMe are very

  使用甲基铝5,10,15,20-四苯基卟啉[（TPP）AlMe]和2,7,12,17-四甲基-3,8,13,18的等摩尔混合物作为引发剂，聚合甲基丙烯酸酯（例如甲基丙烯酸苄酯）尽管从（TPP）AlMe和（EtioP）AlMe的反应性上有很大差异，但从这两种引发剂中衍生出了-四甲基卟啉[（EtioP）AlMe]，得到了分子量分布较窄的单峰聚合物。1 H NMR研究在不存在和存在甲基丙烯酸甲酯（MMA或MMA- d 8），表明两个铝卟啉分子参与了一种非环状过渡态聚合机理，其中无论何时生长的物种总是交换其烯醇盐配体。