(S)-4-(hydroxydiphenylmethyl)oxazolidin-2-one | 173604-32-5

• 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: (S)-4-(hydroxydiphenylmethyl)oxazolidin-2-one
• 英文别名: (S)-4-(hydroxydiphenylmethyl)-2-oxazolidinone；(4S)-4-[hydroxy(diphenyl)methyl]-1,3-oxazolidin-2-one
• CAS: 173604-32-5
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: QANSIXKBTFNELP-AWEZNQCLSA-N

物化性质

• 沸点：
  544.4±19.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-(hydroxydiphenylmethyl)oxazolidin-2-one 在 sodium 作用下， 以 氨 为溶剂， 反应 0.25h， 以79%的产率得到(R)-(+)-4-(二苯基甲基)-2-恶唑烷酮
  参考文献：
  名称：

  Synthesis of N-BOC-D-diphenylalanine from L-serine methyl ester hydrochloride

  摘要：

  A convenient six step synthesis of N-BOC-D-diphenylalanine from L-serine methyl ester hydrochloride is described. The preparation of a novel chiral auxiliary, an oxazolidinone derived from D-diphenylalaninol, is also described.

  DOI：

  10.1016/0040-4039(95)01983-o
• 作为产物：
  描述：

  溴苯 、 (S)-4-methoxycarbonyl-oxazolidin-2-one 在 magnesium 作用下， 以 乙醚 为溶剂， 以64%的产率得到(S)-4-(hydroxydiphenylmethyl)oxazolidin-2-one
  参考文献：
  名称：

  A Ferrocenyl-DHIPOH/Cu(OAc)₂ Complex for Diastereo- and Enantioselective Catalysis of the 1,4-Addition of Glycine Derivatives to Alkylidene Malonates

  摘要：

  A planar chiral ferrocene derivative Fc-DHIPOH served as an excellent N,O- chiral ligand for asymmetric copper catalyzed 1,4-addition of glycine derivatives to alkylidene malonates. The corresponding 1,4-adducts were obtained in high yields with excellent enantioselectivities up to 95% ee.

  DOI：

  10.1021/ol202466v

文献信息

• Chiral N,O-Ligand/[Cu(OAc)₂]-Catalyzed Asymmetric Construction of 4-Aminopyrrolidine Derivatives by 1,3-Dipolar Cycloaddition of Azomethine Ylides with α-Phthalimidoacrylates
  作者：Zheng Wang、Xingxin Yu、Bo-Xue Tian、Daniel T. Payne、Wu-Lin Yang、Yang-Zi Liu、John S. Fossey、Wei-Ping Deng

  DOI：10.1002/chem.201500966

  日期：2015.7.13

  2‐a]pyridine motifs have been evaluated in the asymmetric 1,3‐dipolar cycloaddition of azomethine ylides to α‐phthalimidoacrylates. Reactions catalyzed by copper in combination with ligand 7‐Cl‐DHIPOH provided the highest level of stereoselectivity for the 1,3‐dipolar cycloaddition reaction. The reaction tolerates both β‐substituted and β‐unsubstituted α‐phthalimidoacrylate as dipolarophiles, affording the

  已经开发了一种访问有用的4-氨基吡咯烷-2,4-二羧酸酯衍生物的协议。在偶氮甲亚胺向α-邻苯二甲酰亚胺基丙烯酸酯的不对称1,3-偶极环加成反应中，已经评估了衍生自2,3-二氢咪唑并[1,2-a]吡啶基团的各种手性N，O-配体。铜与配体7-Cl-DHIPOH结合催化​​的反应为1,3-偶极环加成反应提供了最高水平的立体选择性。该反应可耐受β-取代的和β-未取代的α-邻苯二甲酰亚胺基丙烯酸酯作为双极性亲和剂，提供相应的具有非对映异构（> 98：2 dr）和对映选择性（高达97％ee）的季铵化4-氨基吡咯烷环加成物 。可以通过简单的NaBH 4去除邻苯二甲酰亚胺基保护基减少。使用DFT方法进行的理论计算表明，这种环加成反应可能会通过逐步机理进行，并且立体化学在理论上也得到了合理化。
• US5623087A
  申请人：——

  公开号：US5623087A

  公开（公告）日：1997-04-22
• US5939554A
  申请人：——

  公开号：US5939554A

  公开（公告）日：1999-08-17
• A Ferrocenyl-DHIPOH/Cu(OAc)₂ Complex for Diastereo- and Enantioselective Catalysis of the 1,4-Addition of Glycine Derivatives to Alkylidene Malonates
  作者：Yu-Hua Shi、Zheng Wang、Bin Hu、Ming Wang、John S. Fossey、Wei-Ping Deng

  DOI：10.1021/ol202466v

  日期：2011.11.18

  A planar chiral ferrocene derivative Fc-DHIPOH served as an excellent N,O- chiral ligand for asymmetric copper catalyzed 1,4-addition of glycine derivatives to alkylidene malonates. The corresponding 1,4-adducts were obtained in high yields with excellent enantioselectivities up to 95% ee.
• Synthesis of N-BOC-D-diphenylalanine from L-serine methyl ester hydrochloride
  作者：Mukund P. Sibi,·、Prasad K. Deshpande、Anthony J. La Loggia、James W. Christensen

  DOI：10.1016/0040-4039(95)01983-o

  日期：1995.12

  A convenient six step synthesis of N-BOC-D-diphenylalanine from L-serine methyl ester hydrochloride is described. The preparation of a novel chiral auxiliary, an oxazolidinone derived from D-diphenylalaninol, is also described.