[4R,3(2R,3R)]-3-(4-benzyloxy-2,3-dimethylbutanoyl)-4-phenyl-2-oxazolidinone | 1041325-09-0

• 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(2R,3R)]-3-(4-benzyloxy-2,3-dimethylbutanoyl)-4-phenyl-2-oxazolidinone
• 英文别名: (4R)-3-[(2R,3R)-2,3-dimethyl-4-phenylmethoxybutanoyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 1041325-09-0
• 化学式: C₂₂H₂₅NO₄
• 分子量: 367.445
• InChiKey: OBXGJBDBMQWNKF-QKLQHJQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 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(2R,3R)]-3-(4-benzyloxy-2,3-dimethylbutanoyl)-4-phenyl-2-oxazolidinone 在 锂硼氢 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.5h， 以73%的产率得到(2R,3R)-4-benzyloxy-2,3-dimethyl-1-butanol
  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：

  [4R,3(3R)]-3-(4-benzyloxy-3-methylbutanoyl)-4-phenyl-2-oxazolidinone 、 碘甲烷 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 以83%的产率得到[4R,3(2R,3R)]-3-(4-benzyloxy-2,3-dimethylbutanoyl)-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

• 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.