内-2-氯-1,3,3-三甲基二环[2.2.1]庚烷 | 847994-82-5

• 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
• 中文名称: 内-2-氯-1,3,3-三甲基二环[2.2.1]庚烷
• 英文名称: endo-2-chloro-1,3,3-trimethylbicyclo[2.2.1]heptane
• 英文别名: (1R)-2-endo-chlorofenchane；α-fenchyl chloride；sek.-endo-Fenchylchlorid；(1R,2R,4S)-2-chloro-1,3,3-trimethylbicyclo[2.2.1]heptane
• CAS: 847994-82-5
• 化学式: C₁₀H₁₇Cl
• 分子量: 172.698
• InChiKey: ZQEQZOIJQSGLNX-OYNCUSHFSA-N

物化性质

• 沸点：
  200.1±9.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  内-2-氯-1,3,3-三甲基二环[2.2.1]庚烷 、 三苯基氯化锡 在 magnesium 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 β-fenchyltriphenyltin 、 β-fenchyltriphenyltin 、 三苯基氢氧化锡
  参考文献：
  名称：

  Thermal epimerization of diastereomeric Grignard reagents

  摘要：

  热超二聚化是将非对映的硼基和芬基格氏试剂的内外向比分别从 67 : 33 改为 96 : 4 和从 20 : 80 改为 80 : 20 的关键。

  DOI：

  10.1039/b819178f
• 作为产物：
  描述：

  beta-pinene 在 盐酸 作用下， 以 正戊烷 为溶剂， 反应 6.0h， 以13%的产率得到isobornyl chloride
  参考文献：
  名称：

  Thermal epimerization of diastereomeric Grignard reagents

  摘要：

  热超二聚化是将非对映的硼基和芬基格氏试剂的内外向比分别从 67 : 33 改为 96 : 4 和从 20 : 80 改为 80 : 20 的关键。

  DOI：

  10.1039/b819178f

文献信息

• Radical Deoxychlorination of Cesium Oxalates for the Synthesis of Alkyl Chlorides
  作者：Justin Y. Su、Denise C. Grünenfelder、Kohei Takeuchi、Sarah E. Reisman

  DOI：10.1021/acs.orglett.8b02045

  日期：2018.8.17

  A radical deoxychlorination of cesium oxalates has been developed for the preparation of hindered secondary and tertiary alkyl chlorides. The reaction tolerates a number of functional groups, including ketones, alcohols, and amides, and provides complementary reactivity to standard deoxychlorination reactions proceeding by heterolytic mechanisms. Preliminary studies demonstrate that the developed conditions

  草酸铯的自由基脱氧氯化已被开发用于制备受阻的仲和叔烷基氯。该反应可耐受许多官能团，包括酮，醇和酰胺，并为通过杂化机理进行的标准脱氧氯化反应提供互补的反应性。初步研究表明，开发的条件也可用于脱氧溴化和脱氧氟化反应。
• A Remarkably Efficient Markovnikov Hydrochlorination of Olefins and Transformation of Nitriles into Imidates by Use of AcCl and an Alcohol
  作者：Veejendra�K. Yadav、K.�Ganesh Babu

  DOI：10.1002/ejoc.200400591

  日期：2005.1

  mixing AcCl with EtOH brings about Markovnikov hydrochlorination of olefins in excellent yields. The products are isolated in states of high purity simply by removal of the volatile components under reduced pressure. Further, nitriles are transformed into imidate hydrochlorides on similar treatment with AcCl and an alcohol. This procedure for nitrile-imidate transformation is much more efficient than

  通过将 AcCl 与 EtOH 混合产生的 HCl 以极好的收率进行烯烃的马尔科夫尼科夫氢氯化反应。只需在减压下除去挥发性成分，就可以分离出高纯度的产品。此外，腈在用 AcCl 和醇进行类似处理后转化为亚胺酸盐盐酸盐。这种腈-亚胺酸酯转化过程比以前使用的过程更有效，其中包括将 HCl 气体连续通入腈在溶剂（如 Et 2 O 或苯和醇）中的溶液中，直到吸收了等量。
• Toxaphene chemistry: Separation and characterisation of selected enantiomers of the Polychloropinene mixtures
  作者：Alexey Trukhin、Fedor Kruchkov、Lars Kr. Hansen、Roland Kallenborn、Anastasia Kiprianova、Vladimir Nikiforov

  DOI：10.1016/j.chemosphere.2006.05.082

  日期：2007.4

  The primary goal for the study presented here was the preparation and characterisation of enantiomeric pure chlorobornane standards (Toxaphene (R)). In this context, we partially modeled the procedure for Polychloropinene production in the former USSR. The initial reaction was ionic addition of hydrogen chloride to (1S)-alpha-pinene resulting predominantly in (1S)-2-endo-chlorobornane. Further photochlorination gave mixtures of chlorinated terpenes with different average content of Cl per molecule. The resulting mixtures were separated on a silica-gel column and a number of known hepta to decachlorobornanes were identified in fractions with the help of NMR and GC (using electron capture and mass spectrometric detection) - but in very unusual ratios as compared to the technical Toxaphene (R) mixture formerly produced by Hercules (USA). Also several previously unknown congeners were isolated or detected. Three of the isolated congeners were obtained in crystalline state and X-ray crystallography showed their enantionteric purity. (c) 2006 Elsevier Ltd. All rights reserved.
• Thermal epimerization of diastereomeric Grignard reagents
  作者：Jens Beckmann、Alexandra Schütrumpf

  DOI：10.1039/b819178f

  日期：——

  Thermal epimerization is the key to changing the endo-to-exo ratio of the diastereomeric bornyl and fenchyl Grignard reagents from 67 : 33 to 96 : 4 and from 20 : 80 to 80 : 20, respectively.

  热超二聚化是将非对映的硼基和芬基格氏试剂的内外向比分别从 67 : 33 改为 96 : 4 和从 20 : 80 改为 80 : 20 的关键。