3-(3-Naphthalen-2-ylprop-2-enoyl)-1,3-oxazolidin-2-one | 1374559-40-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(3-Naphthalen-2-ylprop-2-enoyl)-1,3-oxazolidin-2-one
• CAS: 1374559-40-6
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: UHDCQWUIAZCTGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  3-(3-Naphthalen-2-ylprop-2-enoyl)-1,3-oxazolidin-2-one 、 Diphenylphosphine oxide 在 吡啶 、 2,6-bis[[(2S)-2-[hydroxy(dithiophen-2-yl)methyl]pyrrolidin-1-yl]methyl]-4-methylphenol 、 diethylzinc 作用下， 以 甲苯 为溶剂， 反应 0.75h， 以95%的产率得到3-[(3S)-3-diphenylphosphoryl-3-naphthalen-2-ylpropanoyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  高效的二芳基膦氧化物不对称迈克尔加成至α，β-不饱和N-酰化的恶唑烷-2-酮

  摘要：

  已开发出一种高效的二芳基氧化膦与α，β-不饱和N-酰化的恶唑烷酮的不对称迈克尔反应。在恶唑烷酮的广泛底物范围内，可获得出色的对映选择性（最高> 99％ee）和化学收率（最高99％）。发现恶唑烷酮的双齿性质对于高对映选择性是关键的。

  DOI：

  10.1002/asia.201200025
• 作为产物：
  描述：

  2-唑烷酮 、 3-(2-naphthyl)acrylic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-(3-Naphthalen-2-ylprop-2-enoyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Asymmetric β-Boration of α,β-Unsaturated N-Acyloxazolidinones by [2.2]Paracyclophane-Based Bifunctional Catalyst

  摘要：

  An efficient copper-catalyzed asymmetric conjugate boration has been achieved by exploiting a new planar and central chiral bicyclic triazolium ligand. This protocol was highly efficient and gave a variety of chiral secondary alkylboronates in 97-99% ee. A preliminary mechanistic study supports the bifunctional nature of the catalyst.

  DOI：

  10.1021/ol302839d

文献信息

• 3-BICYCLOARYL-2-AMINOMETHYL BICYCLOALKANES AS SEROTONINE REUPTAKE INHIBITORS
  申请人：ELI LILLY AND COMPANY LIMITED

  公开号：EP1171416A1

  公开（公告）日：2002-01-16
• US6384281B1
  申请人：——

  公开号：US6384281B1

  公开（公告）日：2002-05-07
• [EN] 3-BICYCLOARYL-2-AMINOMETHYL BICYCLOALKANES AS SEROTONINE REUPTAKE INHIBITORS<br/>[FR] 3-BICYCLOARYLE-2-AMINOMETHYLE BICYCLOALCANES EN TANT QU'INHIBITEURS DE RECAPTAGE DE LA SEROTONINE
  申请人：LILLY CO ELI

  公开号：WO2000061539A1

  公开（公告）日：2000-10-19

  A pharmaceutical compound of formula (I) in which R?1 and R2¿ are each hydrogen or C¿1-4? alkyl, or R?1 and R2¿ together with the nitrogen atom to which they are attached form an azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl or morpholino group, said group being optionally substituted with 1 to 3 C¿1-4? alkyl substituents, R?3¿ is a naphthyl, indolyl, benzothienyl, benzofuranyl, benzothiazolyl, quinolinyl or isoquinolinyl group, said group being optionally substituted, and n is 1 or 2; or a salt or ester thereof.
• Asymmetric β-Boration of α,β-Unsaturated <i>N</i>-Acyloxazolidinones by [2.2]Paracyclophane-Based Bifunctional Catalyst
  作者：Lei Zhao、Yudao Ma、Wenzeng Duan、Fuyan He、Jianqiang Chen、Chun Song

  DOI：10.1021/ol302839d

  日期：2012.11.16

  An efficient copper-catalyzed asymmetric conjugate boration has been achieved by exploiting a new planar and central chiral bicyclic triazolium ligand. This protocol was highly efficient and gave a variety of chiral secondary alkylboronates in 97-99% ee. A preliminary mechanistic study supports the bifunctional nature of the catalyst.
• Highly Efficient Asymmetric Michael Addition of Diaryl Phosphine Oxides to α,β-Unsaturated N-Acylated Oxazolidin-2-ones
  作者：Depeng Zhao、Linqing Wang、Dongxu Yang、Yixin Zhang、Rui Wang

  DOI：10.1002/asia.201200025

  日期：2012.5

  A highly efficient asymmetric Michael reaction of diaryl phosphine oxides with α,β‐unsaturated N‐acylated oxazolidinones has been developed. Excellent enantioselectivities (up to >99 % ee) and chemical yields (up to 99 %) were achieved with a broad substrate scope of the oxazolidinones. The bidentate property of oxazolidinones was found to be critical for high enantioselectivities.

  已开发出一种高效的二芳基氧化膦与α，β-不饱和N-酰化的恶唑烷酮的不对称迈克尔反应。在恶唑烷酮的广泛底物范围内，可获得出色的对映选择性（最高> 99％ee）和化学收率（最高99％）。发现恶唑烷酮的双齿性质对于高对映选择性是关键的。