(S)-(-)-1-acetoxycyclobutabenzene | 139343-58-1

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: (S)-(-)-1-acetoxycyclobutabenzene
• 英文别名: [(7S)-7-bicyclo[4.2.0]octa-1,3,5-trienyl] acetate
• CAS: 139343-58-1
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: XWIPDNKTOPDTBQ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-acetoxybenzocyclobutene 生成 (R)-(+)-1-acetoxycyclobutabenzene 、 (S)-(-)-1-acetoxycyclobutabenzene
  参考文献：
  名称：

  Generation of and cycloaddition to an enantiomerically pure α-oxy-ortho-quinodimethane–tricarbonylchromium complex intermediate

  摘要：

  The reaction of BunLi with either syn- or anti-eta-6-(1-acetoxycyclobutabenzene)Cr(CO)3 generates under mild conditions the planar chiral ortho-quinodimethane complex intermediate 4 which reacts with dienophiles (methyl acrylate, acrylonitrile, dimethyl fumarate) highly stereoselectively from the face opposite the metal to give the anti-1-hydroxytetrahydronaphthalene-Cr(CO)3 complexes (X-ray structures of 5 and 6) and, after decomplexation, the 1-hydroxytetrahydronaphthalenes 7-14 (asymmetric synthesis of 7 and 8).

  DOI：

  10.1039/c39910001713

文献信息

• Chiral tricarbonyl(η6-cyclobutabenzene)chromium complexes. Diastereoselective synthesis and use in asymmetric cycloaddition reactions
  作者：E. Peter Kündig、James Leresche、Lionel Saudan、Gérald Bernardinelli

  DOI：10.1016/0040-4020(96)00257-8

  日期：1996.5

  The intermolecular Diels-Alder reaction of a nonracemic planar chiral (ortho-quinodimethane)Cr(CO)3 intermediate 6 with dienophiles gave, after decomplexation, chiral nonracemic tetralins 23–25. Access to 6 was obtained via enzyme catalyzed acetate hydrolysis of 1-acetoxycyclobutabenzene (13), derivatization of the highly enantioenriched 1-hydroxycyclobutabenzene (S-(+)-8) as the tetrahydropyranyl

  非外消旋的平面手性（邻-喹二甲烷）Cr（CO）3中间体6与亲二烯体的分子间Diels-Alder反应在分解后产生了手性的非外消旋四氢化萘23-25。通过酶催化的1-乙酰氧基环丁苯的乙酸水解（13），高度对映体富集的1-羟基环丁苯（S-（+）- 8）的四氢吡喃基醚20非对映选择性络合为Cr（CO）3的方法获得6的通道。 （1-羟基环丁苯）Cr（CO）的阴离子的水解和电荷加速开环3（（1S，6aR）-（-）- 4）。
• Generation of and cycloaddition to an enantiomerically pure α-oxy-ortho-quinodimethane–tricarbonylchromium complex intermediate
  作者：E. Peter Kündig、Gérald Bernardinelli、James Leresche

  DOI：10.1039/c39910001713

  日期：——

  The reaction of BunLi with either syn- or anti-eta-6-(1-acetoxycyclobutabenzene)Cr(CO)3 generates under mild conditions the planar chiral ortho-quinodimethane complex intermediate 4 which reacts with dienophiles (methyl acrylate, acrylonitrile, dimethyl fumarate) highly stereoselectively from the face opposite the metal to give the anti-1-hydroxytetrahydronaphthalene-Cr(CO)3 complexes (X-ray structures of 5 and 6) and, after decomplexation, the 1-hydroxytetrahydronaphthalenes 7-14 (asymmetric synthesis of 7 and 8).