N-acetyl-N-methylglycine 2-(di-o-tolylphosphino)phenol ester | 254441-33-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-acetyl-N-methylglycine 2-(di-o-tolylphosphino)phenol ester
• 英文别名: [2-Bis(2-methylphenyl)phosphanylphenyl] 2-[acetyl(methyl)amino]acetate
• CAS: 254441-33-3
• 化学式: C₂₅H₂₆NO₃P
• 分子量: 419.46
• InChiKey: UPUCNTQWSKVWFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  di-μ-chloro-bis[bis(cyclo-octene)rhodium] 、 N-acetyl-N-methylglycine 2-(di-o-tolylphosphino)phenol ester 以 氘代苯 为溶剂， 生成
  参考文献：
  名称：

  Controlled oxidative addition of amino acid esters to Rh(I)

  摘要：

  The new sterically demanding phosphine 2-(di-o-tolylphosphino)phenol was prepared and used to create a series of esters with N-acylated amino acids. The phosphine-containing esters react within 30-60 min at room temperature with [(mu-Cl)Rh(cyclooctene)(2)](2) to give products of oxidative addition of the ester carbonyl-oxygen bond to the Rh center. The N-acyl carbonyl oxygen is bound to the Rh in these initial adducts, but is displaced upon addition of PMe3. Remarkably, both initial products and their PMe3 adducts are formed as single five-coordinate diastereomers in essentially quantitative yields. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(99)00311-3
• 作为产物：
  描述：

  1-(甲氧基甲氧基)苯 在 盐酸 、 4-二甲氨基吡啶 、 叔丁基锂 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 N-acetyl-N-methylglycine 2-(di-o-tolylphosphino)phenol ester
  参考文献：
  名称：

  Controlled oxidative addition of amino acid esters to Rh(I)

  摘要：

  The new sterically demanding phosphine 2-(di-o-tolylphosphino)phenol was prepared and used to create a series of esters with N-acylated amino acids. The phosphine-containing esters react within 30-60 min at room temperature with [(mu-Cl)Rh(cyclooctene)(2)](2) to give products of oxidative addition of the ester carbonyl-oxygen bond to the Rh center. The N-acyl carbonyl oxygen is bound to the Rh in these initial adducts, but is displaced upon addition of PMe3. Remarkably, both initial products and their PMe3 adducts are formed as single five-coordinate diastereomers in essentially quantitative yields. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(99)00311-3

文献信息

• Oxidative addition of the C–O bond of amino acid esters to Rh(I) forming chelating acyl complexes
  作者：Douglas B Grotjahn、Camil Joubran

  DOI：10.1016/j.ica.2004.05.028

  日期：2004.7

  Esters of N-acylated amino acids and the sterically demanding phosphine 2-(di-ortho-tolylphosphino)phenol react within 1 h at room temperature with the Rh(I) centers of [Cl(μ-Cl)Rh(cyclooctene)2]2 to give products of oxidative addition of the ester carbonyl–O bond. The N-acyl carbonyl oxygen is bound to the Rh in these initial adducts, but is displaced upon addition of PMe3, PhPMe2, NH2NMe2, or the

  N酰化氨基酸的酯和空间需求的膦2-（二-邻甲苯基膦基）苯酚在室温下1小时内与[Cl（μ-Cl）Rh（环辛烯）2]的Rh（I）中心反应。 2得到酯羰基-O键的氧化加成产物。在这些初始加合物中，N-酰基羰基氧与Rh结合，但是在添加PMe3，PhPMe2，NH2NMe2或蛋氨酸衍生物的硫醚官能团后被取代。值得注意的是，来自非手性氨基酸的初始产物及其配体加合物均以基本上定量的产率形成为单个五配位非对映异构体。然而，脯氨酸和苯丙氨酸的手性氨基酸衍生物对Rh立体化学的不对称诱导作用是适度的。最后，