3a-O-benzyl 2-O,2-O',5-O-triethyl (3aS,5S,7aS)-6,7-dimethylidene-3,4,5,7a-tetrahydro-1H-indene-2,2,3a,5-tetracarboxylate | 1415145-48-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3a-O-benzyl 2-O,2-O',5-O-triethyl (3aS,5S,7aS)-6,7-dimethylidene-3,4,5,7a-tetrahydro-1H-indene-2,2,3a,5-tetracarboxylate
• CAS: 1415145-48-0
• 化学式: C₂₈H₃₄O₈
• 分子量: 498.573
• InChiKey: ZOXHKNFCFSOKOG-BERHBOFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  but-3,4-dienylmalonate 、 2-bromomethylacrylic acid benzyl ester 在 chlorobis(ethylene)rhodium(I) dimer 、 silver trifluoromethanesulfonate 、 sodium hydride 、 C.I.酸性棕21 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 2.17h， 生成 3a-O-benzyl 2-O,2-O',5-O-triethyl (3aS,5S,7aS)-6,7-dimethylidene-3,4,5,7a-tetrahydro-1H-indene-2,2,3a,5-tetracarboxylate 、
  参考文献：
  名称：

  Enantioselective Intermolecular [2 + 2 + 2] Cycloadditions of Ene–Allenes with Allenoates

  摘要：

  An enantioselective [2 + 2 + 2] cycloaddition of ene-allenes with allenoates is described, which transforms simple pi-components into stereochemically complex carbocycles in a single step. The rhodium(I)-catalyzed cycloaddition proceeds with good levels of enantioselectivity, and with high levels of regio-, chemo-, and diastereoselectivity. Our results are consistent with a mechanism involving an enantioselective intermolecular allene-allene oxidative coupling.

  DOI：

  10.1021/ol303024q

文献信息

• Enantioselective Intermolecular [2 + 2 + 2] Cycloadditions of Ene–Allenes with Allenoates
  作者：Andrew T. Brusoe、Rahul V. Edwankar、Erik J. Alexanian

  DOI：10.1021/ol303024q

  日期：2012.12.7

  An enantioselective [2 + 2 + 2] cycloaddition of ene-allenes with allenoates is described, which transforms simple pi-components into stereochemically complex carbocycles in a single step. The rhodium(I)-catalyzed cycloaddition proceeds with good levels of enantioselectivity, and with high levels of regio-, chemo-, and diastereoselectivity. Our results are consistent with a mechanism involving an enantioselective intermolecular allene-allene oxidative coupling.