N1,n3-双((r)-2-羟基-1-苯基乙基)-2,2-二甲基丙二酰胺 | 178958-49-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N1,n3-双((r)-2-羟基-1-苯基乙基)-2,2-二甲基丙二酰胺
• 英文名称: N¹,N³-bis((R)-2-hydroxy-1-phenylethyl)-2,2-dimethylmalonamide
• 英文别名: N1,N3-bis((R)-2-hydroxy-1-phenylethyl)-2,2-dimethylmalonamide；N,N'-bis[(1R)-2-hydroxy-1-phenylethyl]-2,2-dimethylpropanediamide
• CAS: 178958-49-1
• 化学式: C₂₁H₂₆N₂O₄
• 分子量: 370.448
• InChiKey: NTTZCNSPNMRTSV-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N1,n3-双((r)-2-羟基-1-苯基乙基)-2,2-二甲基丙二酰胺 在 polyethyleneglycol-linked N-(triethylammonium-sulfonyl)carbamate 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 3.0h， 以80%的产率得到(R,R)-2,2'-异亚丙基双(4-苯基-2-恶唑啉)
  参考文献：
  名称：

  PEG支撑的Burgess试剂用于吡咯合成的改进方案

  摘要：

  开发了与聚乙二醇连接的Burgess试剂，并将其用于β-羟基酰胺和硫代酰胺的环脱水。以高收率和优异的纯度获得了所需的恶唑啉和噻唑啉。聚合物键合试剂的主要优点是其易处理性提高，并且在不稳定的恶唑啉的合成中产率大大提高。

  DOI：

  10.1016/0040-4039(96)00918-5
• 作为产物：
  描述：

  D-苯甘氨醇 、 二甲基丙二酰二氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以75%的产率得到N1,n3-双((r)-2-羟基-1-苯基乙基)-2,2-二甲基丙二酰胺
  参考文献：
  名称：

  Hydrogen bonding topology influences gelating properties of malonamides

  摘要：

  介绍了双(苯基甘氨醇)丙二酰胺及其 Cα 单烷基和二烷基取代衍生物的制备、结构特征和氢键网络拓扑结构。从它们的胶凝特性角度描述了它们的氢键结构。并将丙二酰胺胶凝剂典型的氢键拓扑结构与经过充分研究的草酰胺胶凝剂的氢键拓扑结构进行了比较。

  DOI：

  10.1007/s11224-012-0102-3

文献信息

• An improved protocol for azole synthesis with PEG-supported Burgess reagent
  作者：Peter Wipf、Srikanth Venkatraman

  DOI：10.1016/0040-4039(96)00918-5

  日期：1996.7

  polyethyleneglycol-linked version of Burgess reagent was developed and applied toward the cyclodehydration of β-hydroxy amides and thioamides. The desired oxazolines and thiazolines were obtained in high yields and excellent purities. The major advantages of the polymer bound reagent are its improved ease of handling and greatly increased yields in the synthesis of labile oxazolines.

  开发了与聚乙二醇连接的Burgess试剂，并将其用于β-羟基酰胺和硫代酰胺的环脱水。以高收率和优异的纯度获得了所需的恶唑啉和噻唑啉。聚合物键合试剂的主要优点是其易处理性提高，并且在不稳定的恶唑啉的合成中产率大大提高。
• METHOD FOR PRODUCING OPTICALLY ACTIVE BISAMIDO ALCOHOL COMPOUND
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1698616A1

  公开（公告）日：2006-09-06

  It is provided that a method for producing an optically active bisamidoalcohol compound represented by the formula (3): wherein R1 represents a C1-6 alkyl group, an optionally substituted phenyl group, an optionally substituted aralkyl group or a hydrogen atom, or two R1s, which are bonded to the same carbon atom, are bonded to form a ring together with the carbon atom to which they are bonded, R2 represents a C1-6 alkyl group, an optionally substituted phenyl group, a 1-naphthyl group, a 2-naphthyl group or an optionally substituted aralkyl group, R3 and R4 are the same or different, and each represents a hydrogen atom or C1-3 alkyl group, m represents an integer of 0 to 2, and * represents an asymmetric center, which comprises reacting an optically active aminoalcohol compound represented by the formula (1): wherein R1, R2 and * are as defined above, with a diester compound represented by the formula (2): wherein R3, R4 and m are as defined above and R5 represents a C1-3 alkyl group, in the presence of a lithium compound.

  本发明提供了一种生产由式（3）代表的光学活性双氨基醇化合物的方法： 其中 R1 代表 C1-6 烷基、任选取代的苯基、任选取代的芳烷基或氢原子，或两个 R1 与同一碳原子键合，与其键合的碳原子一起形成环、 R2 代表 C1-6 烷基、任选取代的苯基、1-萘基、2-萘基或任选取代的芳基、 R3 和 R4 相同或不同，各自代表氢原子或 C1-3 烷基、 m 代表 0 至 2 的整数，以及 * 代表不对称中心，其中包括与由式（1）代表的光学活性氨基醇化合物反应： 其中 R1、R2 和 * 如上定义、 与式 (2) 所代表的二酯化合物反应： 其中 R3、R4 和 m 如上定义，R5 代表 C1-3 烷基、 在锂化合物存在下。
• Method for producing optically active bisamidoalcohol compound
  申请人：Itagaki Makoto

  公开号：US20070100163A1

  公开（公告）日：2007-05-03

  It is provided that a method for producing an optically active bisamidoalcohol compound represented by the formula (3): wherein R 1 represents a C1-6 alkyl group, an optionally substituted phenyl group, an optionally substituted aralkyl group or a hydrogen atom, or two R 1 s, which are bonded to the same carbon atom, are bonded to form a ring together with the carbon atom to which they are bonded, R 2 represents a C1-6 alkyl group, an optionally substituted phenyl group, a 1-naphthyl group, a 2-naphthyl group or an optionally substituted aralkyl group, R 3 and R 4 are the same or different, and each represents a hydrogen atom or C1-3 alkyl group, m represents an integer of 0 to 2, and * represents an asymmetric center, which comprises reacting an optically active aminoalcohol compound represented by the formula (1): wherein R 1 , R 2 and * are as defined above, with a diester compound represented by the formula (2): wherein R 3 , R 4 and m are as defined above and R 5 represents a C1-3 alkyl group, in the presence of a lithium compound.
• US7612236B2
  申请人：——

  公开号：US7612236B2

  公开（公告）日：2009-11-03
• Studies on a catalytic version of the Matteson asymmetric homologation reaction
  作者：Keith Smith、Basil A. Saleh、Mohammed B. Alshammari、Gamal A. El-Hiti、Mark C. Elliott

  DOI：10.1039/d1ob00604e

  日期：——

  Studies of a catalytic asymmetric version of the Matteson reaction between dichloromethylboronates and organolithium reagents have been undertaken. From several different chiral catalytic systems studied, only one based on a mannitol derivative has given substantial asymmetric induction close to that previously achieved with a bis(oxazoline) derivative and ytterbium triflate. More detailed study of

  已经对二氯甲基硼酸盐和有机锂试剂之间的马特森反应的催化不对称形式进行了研究。从研究的几种不同的手性催化系统中，只有一种基于甘露醇衍生物的不对称诱导接近于以前用双（恶唑啉）衍生物和三氟甲磺酸镱实现的不对称诱导。对后一种反应的更详细研究表明，新鲜的三氟甲磺酸镱实际上降低了不对称诱导的水平，而“老化的”三氟甲磺酸镱，或用水处理过的新鲜样品，带来了改进的诱导。讨论了这些发现的含义。