2-(1,1,2,3,3-pentamethyl-2H-inden-5-yl)prop-2-enoic acid | 554402-82-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(1,1,2,3,3-pentamethyl-2H-inden-5-yl)prop-2-enoic acid
• CAS: 554402-82-3
• 化学式: C₁₇H₂₂O₂
• 分子量: 258.36
• InChiKey: KOLBDTLAUHXIEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1,1,2,3,3-pentamethyl-2H-inden-5-yl)prop-2-enoic acid 在 [RuCl2(benzene)]2 氢气 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三乙胺 、 sodium tetrahydroborate 、 碘 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (-)-(βS,2R)/(βS,2S)-β,1,1,2,3,3-hexamethylindan-5-ethanol 、 (+)-(βR,2R)/(βR,2S)-β,1,1,2,3,3,-hexamethylindan-5-ethanol
  参考文献：
  名称：

  Asymmetric catalysis in fragrance chemistry: a new synthesis of Galaxolide®

  摘要：

  A new synthesis of the olfactorally active stereoisomers of the musk odorant Galaxolide is reported. The key step is the ruthenium-catalysed asymmetric hydrogenation of an a-aryl acrylic acid: asymmetric inductions up to 89% have been achieved using a catalytic system prepared in situ by mixing [Ru(benzene)Cl-2](2) with (S)-BINAP. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00538-4
• 作为产物：
  描述：

  2-methyl-4-(1,1,2,3,3-pentamethyl-2H-inden-5-yl)but-3-yn-2-ol 在 palladium diacetate 氢氧化钾 、 PyPPh₂ 作用下， 以 四氢呋喃 、 水 、 异丙醇 为溶剂， 生成 2-(1,1,2,3,3-pentamethyl-2H-inden-5-yl)prop-2-enoic acid
  参考文献：
  名称：

  Asymmetric catalysis in fragrance chemistry: a new synthesis of Galaxolide®

  摘要：

  A new synthesis of the olfactorally active stereoisomers of the musk odorant Galaxolide is reported. The key step is the ruthenium-catalysed asymmetric hydrogenation of an a-aryl acrylic acid: asymmetric inductions up to 89% have been achieved using a catalytic system prepared in situ by mixing [Ru(benzene)Cl-2](2) with (S)-BINAP. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00538-4

文献信息

• Asymmetric catalysis in fragrance chemistry: a new synthesis of Galaxolide®
  作者：Alessandra Ciappa、Ugo Matteoli、Alberto Scrivanti

  DOI：10.1016/s0957-4166(02)00538-4

  日期：2002.10

  A new synthesis of the olfactorally active stereoisomers of the musk odorant Galaxolide is reported. The key step is the ruthenium-catalysed asymmetric hydrogenation of an a-aryl acrylic acid: asymmetric inductions up to 89% have been achieved using a catalytic system prepared in situ by mixing [Ru(benzene)Cl-2](2) with (S)-BINAP. (C) 2002 Elsevier Science Ltd. All rights reserved.