ketopinic acid methyl ester | 125637-45-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ketopinic acid methyl ester
• 英文别名: (1S)-(+)-ketopinic acid methyl ester；methyl 7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylate；methyl (1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylate
• CAS: 125637-45-8
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: RVNZADBGUKKLTO-HQJQHLMTSA-N

物化性质

• 熔点：
  37-39 °C
• 沸点：
  256.3±23.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ketopinic acid methyl ester 以95%的产率得到(S)-(+)-酮基蒎酸
  参考文献：
  名称：

  Synthesis of (+)-(1S,4R)-1-(1-chlorovinyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one

  摘要：

  DOI：

  10.1007/s11178-005-0022-4
• 作为产物：
  描述：

  7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carbaldehyde 在 air 作用下， 生成 ketopinic acid methyl ester
  参考文献：
  名称：

  Asahina; Ishidate, Chemische Berichte, 1934, vol. 67, p. 1202,1204

  摘要：

  DOI：

文献信息

• Enantioselective addition of diethylzinc to aldehydes in the presence of chiral hydrazone and imine ligands
  作者：Takashi Mino、Atsushi Suzuki、Masakazu Yamashita、Shusaku Narita、Yoshiaki Shirae、Masami Sakamoto、Tsutomu Fujita

  DOI：10.1016/j.jorganchem.2006.07.006

  日期：2006.10

  Optically active hydrazone and imine were found to act as effective ligands for enantioselective addition of diethylzinc to aldehydes. This reaction provided optically active secondary alcohols with ee up to 71%.

  发现光学活性和亚胺可作为二乙基锌对醛对映选择性加成的有效配体。该反应提供了具有高达71％ee的旋光仲醇。
• Dichloromethane Activation. Direct Methylenation of Ketones and Aldehydes with CH₂Cl₂ Promoted by Mg/TiCl₄/THF
  作者：Tu-Hsin Yan、Chia-Chung Tsai、Ching-Ting Chien、Chia-Ching Cho、Pei-Chen Huang

  DOI：10.1021/ol0478887

  日期：2004.12.1

  [reaction: see text] This Mg-TiCl4-promoted CH2-transfer reaction of CH2Cl2 represents an extremely simple, practical, and efficient methylenation of a variety of ketones and aldehydes, especially in enolizable or sterically hindered ketones such as 2,2-dimethylcyclohexanone, camphor, and fenchone.

  [反应：查看文本]这种由Mg-TiCl4促进的CH2Cl2的CH2转移反应代表了各种酮和醛的极其简单，实用和有效的亚甲基化，特别是在可烯醇化或空间受阻的酮（如2,2-二甲基环己酮）中，樟脑和fenchone。
• Facile synthesis of isocampholenic acids by the rearrangement of camphor derivatives
  作者：Robyn Aryn Biggs、William W. Ogilvie

  DOI：10.1016/j.tet.2012.12.011

  日期：2013.2

  A variety of substituted isocampholenic acid derivatives were prepared by rearrangement of the camphor skeleton of a variety of tertiary alcohols derived from ketopinic acid. The reaction was highly reliable and retained the stereochemical information from the camphor scaffold. This rearrangement represents an efficient way to prepare synthetically useful isocampholenic acids. Mechanistic experiments

  通过重排衍生自酮多酸的各种叔醇的樟脑骨架，制备了各种取代的异樟脑酸衍生物。该反应是高度可靠的，并且保留了来自樟脑支架的立体化学信息。这种重排代表了制备合成上有用的异马来酸的有效方法。机理实验表明，该反应涉及短寿命的碳正离子化。
• [EN] PROCESS FOR THE PREPARATION OF HU-910 AND CRYSTALLINE STRUCTURE THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION DE HU-910 ET STRUCTURE CRISTALLINE ASSOCIÉE
  申请人：YISSUM RES DEV CO OF HEBREW UNIV JERUSALEM LTD

  公开号：WO2018087767A1

  公开（公告）日：2018-05-17

  The invention provides processes for the preparation of HU-910, which are scalable to industrial purposes, using safer reagents and having high yield and pure product and a crystalline structure of HU-910, which is a unique product thereof.

  这项发明提供了用于制备HU-910的工艺，这些工艺可扩展至工业用途，使用更安全的试剂，产率高，产品纯度高，并具有独特的结晶结构的HU-910。
• Chiral P,N-Ligands Based on Ketopinic Acid in the Asymmetric Heck Reaction
  作者：Scott R. Gilbertson、Zice Fu

  DOI：10.1021/ol006747b

  日期：2001.1.1

  [figure: see text] Novel chiral P,N-ligands were synthesized from (1S)-(+)-ketopinic acid using palladium-catalyzed coupling reaction of a vinyl triflate and either a diarylphosphine or a dialkylphosphine as the key step. Palladium complexes of these ligands are efficient catalysts for asymmetric Heck reaction between aryl or alkenyl triflates and cyclic alkenes. Products were obtained with good to

  [图：见正文]使用钯催化的三氟甲磺酸乙烯酯与二芳基膦或二烷基膦的偶联反应，由（1S）-（+）-酮酸合成了新型手性P，N-配体。这些配体的钯配合物是芳基或链烯基三氟甲磺酸酯与环状烯烃之间不对称Heck反应的有效催化剂。从1，2-二氢呋喃，环戊烯和4，7-二氢-1，3-二氧杂环丁烷的芳基化和烯基化获得具有良好至优异对映选择性的产物。