cis-6-hydroxybicyclo<4.4.0>decan-2-one | 3468-73-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-6-hydroxybicyclo<4.4.0>decan-2-one
• 英文别名: 4a-hydroxy-octahydro-naphthalen-1-one；(4aS,8aR)-4a-hydroxy-2,3,4,5,6,7,8,8a-octahydronaphthalen-1-one
• CAS: 3468-73-3；77951-54-3；91057-04-4
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: ACPBKLXVRRPRFF-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  cis-6-hydroxybicyclo<4.4.0>decan-2-one 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 以92%的产率得到3,4,5,6,7,8-hexahydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Kopecky, Karl R.; Lockwood, Peter A.; Gomez, Rodrigo Rico, Canadian Journal of Chemistry, 1981, vol. 59, p. 851 - 858

  摘要：

  DOI：
• 作为产物：
  描述：

  1(7)-二环(5.3.0)癸烷 在 铂 氢气 、 臭氧 作用下， 生成 cis-6-hydroxybicyclo<4.4.0>decan-2-one
  参考文献：
  名称：

  Kopecky, Karl R.; Lockwood, Peter A.; Gomez, Rodrigo Rico, Canadian Journal of Chemistry, 1981, vol. 59, p. 851 - 858

  摘要：

  DOI：

文献信息

• Cerium(IV)-Catalyzed Deprotection of Acetals and Ketals under Mildly Basic Conditions
  作者：István E. Markó、Ali Ates、Arnaud Gautier、Bernard Leroy、Jean-Marc Plancher、Yannick Quesnel、Jean-Christophe Vanherck

  DOI：10.1002/(sici)1521-3773(19991102)38:21<3207::aid-anie3207>3.0.co;2-i

  日期：1999.11.2

  Smooth and quantitative deprotection of a wide range of acetals and ketals [Eq. (a); R, R(1)=alkyl, aryl, H] under neutral to mildly basic conditions was achieved with catalytic quantities of cerium ammonium nitrate (CAN). The reaction conditions are compatible with a variety of sensitive functional groups, and aldehydes can be liberated from acetals without being oxidized to the corresponding carboxylic

  各种缩醛和缩酮的平滑定量脱保护[Eq。（一种）; R，R（1）=烷基，芳基，H]在中性至弱碱性条件下用催化量的硝酸铈铵（CAN）实现。反应条件与各种敏感的官能团相容，并且醛可以从缩醛中释放出来而不会被氧化为相应的羧酸。
• Mild and chemoselective catalytic deprotection of ketals and acetals using cerium(IV) ammonium nitrate
  作者：Ali Ates、Arnaud Gautier、Bernard Leroy、Jean-Marc Plancher、Yannick Quesnel、Jean-Christophe Vanherck、István E Markó

  DOI：10.1016/j.tet.2003.03.002

  日期：2003.11

  Cerium(IV) ammonium nitrate (CAN) is a powerful, though mild, reagent for the efficient and selective removal of a range of ketals and acetals. This novel deprotection method requires only catalytic amounts of CAN and tolerates a variety of functional and protecting groups. Mechanistic insights suggest that the Ce(IV) salts act as unique Lewis acids and not as redox active species.

  硝酸铈（IV）铵（CAN）是一种功能强大的试剂，尽管温和，但可以有效，选择性地去除一系列缩酮和乙缩醛。这种新颖的脱保护方法仅需要催化量的CAN，并能耐受各种功能和保护基团。机械学的见解表明，Ce（IV）盐起独特的路易斯酸的作用，而不是氧化还原活性物质。
• Remarkably efficient deprotection of cyclic acetals and ketals
  作者：Ali Ates、Arnaud Gautier、Bernard Leroy、Jean-Marc Plancher、Yannick Quesnel、István E Markó

  DOI：10.1016/s0040-4039(99)00013-1

  日期：1999.2

  A simple and mild procedure for the efficient deprotection of cyclic acetals and ketals, using cerium ammonium nitrate (CAN) is reported. The method tolerates a range of functional and protecting groups and is suitable for acid-labile substrates.

  据报道，使用硝酸铈铵（CAN）可以简单，温和地有效去除环缩醛和缩酮。该方法可耐受一定范围的官能团和保护基，适用于酸不稳定的底物。
• Efficient access to functionalised medium-ring systems by radical fragmentation/radical addition to α-iodoketones
  作者：Corinne De Dobbeleer、Ali Ates、Jean-Christophe Vanherk、István E. Markó

  DOI：10.1016/j.tetlet.2005.03.200

  日期：2005.5

  Functionalised medium-ring systems of various sizes can be efficiently prepared by a novel approach that embodies a radical-induced fragmentation of bicyclic P-hydroxy ketones, followed by a second radical-coupling reaction. The unexpected reactivity of ot-keto radicals is also discussed. (c) 2005 Elsevier Ltd. All rights reserved.