(5S,6R)-5,6-dimethyl-3-methyleneoxepan-2-one | 1041324-94-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (5S,6R)-5,6-dimethyl-3-methyleneoxepan-2-one
• 英文别名: (5S,6R)-5,6-dimethyl-3-methylideneoxepan-2-one
• CAS: 1041324-94-0
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: SZMFWHMNDDANTD-XPUUQOCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5S,6R)-5,6-dimethyl-3-methyleneoxepan-2-one 、 (2S,5R,6R,8R,10R)-2-(2-benzyloxy)ethyl-10-[(1S,2R,3R,5R,7S)-2-(tert-butyldimethylsilyl)oxy-[(1E)-3-(tert-butyldiphenylsilyl)oxymethylbuta-1,3-dienyl]-3-methyl-6,8-dioxabicyclo[3.2.1]octan-5-ylmethyl]-5-methyl-5-(triethylsilyl)oxy-1,7,9-trioxadispiro[5.1.5.2]pentadecane 以 对二甲苯 为溶剂， 反应 12.0h， 以35%的产率得到(1S,6R,10R,11S)-1-[(1S,2R,3R,5R,7S)-5-[(2S,5R,6R,8R,10R)-2-(2-benzyloxy)ethyl-5-methyl-5-(triethylsilyl)oxy-1,7,9-trioxadispiro[5.1.5.2]pentadecan-10-ylmethyl]-2-(tert-butyldimethylsilyl)oxy-3-methyl-6,8-dioxabicyclo[3.2.1]octan-7-yl]-3-(tert-butyldiphenylsilyl)oxymethyl-10,11-dimethyl-8-oxaspiro[5.6]dodec-2-en-7-one
  参考文献：
  名称：

  品纳毒素A的全合成。

  摘要：

  DOI：

  10.1002/anie.200802729
• 作为产物：
  描述：

  以 甲苯 为溶剂， 反应 3.0h， 以572 mg的产率得到(5S,6R)-5,6-dimethyl-3-methyleneoxepan-2-one
  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

• Total Synthesis of Pinnatoxin A
  作者：Seiichi Nakamura、Fumiaki Kikuchi、Shunichi Hashimoto

  DOI：10.1002/anie.200802729

  日期：2008.9.1
• 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.