[4R,3(2E)]-3-(4-benzyloxy-2-butenoyl)-4-phenyl-2-oxazolidinone | 1041325-04-5

• 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: [4R,3(2E)]-3-(4-benzyloxy-2-butenoyl)-4-phenyl-2-oxazolidinone
• 英文别名: (R)-3((E)-4-(benzyloxy)but-2-enoyl)-4-phenyloxazolidin-2-one；(4R)-4-phenyl-3-[(E)-4-phenylmethoxybut-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 1041325-04-5
• 化学式: C₂₀H₁₉NO₄
• 分子量: 337.375
• InChiKey: ZCOUQWNKXQOIKT-NUCSPZLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [4R,3(2E)]-3-(4-benzyloxy-2-butenoyl)-4-phenyl-2-oxazolidinone 、 甲基溴化镁 在 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 以72%的产率得到[4R,3(3R)]-3-(4-benzyloxy-3-methylbutanoyl)-4-phenyl-2-oxazolidinone
  参考文献：
  名称：

  Stereoselective synthesis of a C1–C6 fragment of pinnatoxin A via a 1,4-addition/alkylation sequence

  摘要：

  A C1-C6 fragment of pinnatoxin A, (5S,6R)-5,6-dimethyl-3-methyleneoxepan-2-one, which features a gamma,delta-trans-dimethyl-substituted alpha-methylene lactone, has been synthesized in an enantiomerically pure form from ethyl (E)-4-benzyloxy-2-butenoate through an auxiliary-based conjugate addition and alkylation reaction. The excellent diastereoselectivity (98:2) observed in the alkylation reaction is the result of stereocontrol from both the adjacent stereocenter and the chiral oxazolidinone. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.013
• 作为产物：
  描述：

  (R)-4-苯基-2-唑烷酮 、 (E)-4-(benzyloxy)but-2-enoic acid 在 三甲基乙酰氯 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 [4R,3(2E)]-3-(4-benzyloxy-2-butenoyl)-4-phenyl-2-oxazolidinone
  参考文献：
  名称：

  Stereoselective synthesis of a C1–C6 fragment of pinnatoxin A via a 1,4-addition/alkylation sequence

  摘要：

  A C1-C6 fragment of pinnatoxin A, (5S,6R)-5,6-dimethyl-3-methyleneoxepan-2-one, which features a gamma,delta-trans-dimethyl-substituted alpha-methylene lactone, has been synthesized in an enantiomerically pure form from ethyl (E)-4-benzyloxy-2-butenoate through an auxiliary-based conjugate addition and alkylation reaction. The excellent diastereoselectivity (98:2) observed in the alkylation reaction is the result of stereocontrol from both the adjacent stereocenter and the chiral oxazolidinone. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.013

文献信息

• Efficient asymmetric synthesis of the functionalized pyroglutamate core unit common to oxazolomycin and neooxazolomycin using Michael reaction of nucleophilic glycine Schiff base with α,β-disubstituted acrylate
  作者：Takeshi Yamada、Kazuhiko Sakaguchi、Tetsuro Shinada、Yasufumi Ohfune、Vadim A. Soloshonok

  DOI：10.1016/j.tetasy.2008.11.036

  日期：2008.12

  The functionalized pyroglutamate core unit, (2R,4R)-3, which could be converted into the beta-lactone/pyrrolidine or gamma-lactone/pyrrolidine ring system of oxazolomycin A 1 and neooxazolomycin 2, and which possesses an exomethylene group at C3 as a scaffold for the Construction of their C3 polyene segment, was synthesized by the Michael reaction of a glycine Schiff base 4 with the alpha,beta-disubstituted acrylate 8 as the key step. (C) 2008 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of a C1–C6 fragment of pinnatoxin A via a 1,4-addition/alkylation sequence
  作者：Seiichi Nakamura、Fumiaki Kikuchi、Shunichi Hashimoto

  DOI：10.1016/j.tetasy.2008.04.013

  日期：2008.5

  A C1-C6 fragment of pinnatoxin A, (5S,6R)-5,6-dimethyl-3-methyleneoxepan-2-one, which features a gamma,delta-trans-dimethyl-substituted alpha-methylene lactone, has been synthesized in an enantiomerically pure form from ethyl (E)-4-benzyloxy-2-butenoate through an auxiliary-based conjugate addition and alkylation reaction. The excellent diastereoselectivity (98:2) observed in the alkylation reaction is the result of stereocontrol from both the adjacent stereocenter and the chiral oxazolidinone. (C) 2008 Elsevier Ltd. All rights reserved.