2-(trichloromethyl)-2,3-dihydro-1H-inden-2-ol | 1361392-62-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(trichloromethyl)-2,3-dihydro-1H-inden-2-ol
• 英文别名: 2-(Trichloromethyl)-1,3-dihydroinden-2-ol
• CAS: 1361392-62-2
• 化学式: C₁₀H₉Cl₃O
• 分子量: 251.54
• InChiKey: VXTNBQHAROVSQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-茚酮 在 四丁基氟化铵 、 溶剂黄146 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 为溶剂， 反应 0.67h， 生成 2-(trichloromethyl)-2,3-dihydro-1H-inden-2-ol
  参考文献：
  名称：

  One-Pot in Situ Formation and Reaction of Trimethyl(trichloromethyl)silane: Application to the Synthesis of 2,2,2-Trichloromethylcarbinols

  摘要：

  2,2,2-Trichloromethylcarbinols are 1 are valuable synthetic intermediates with a multitude of uses. A scalable procedure for the synthesis of TMS-protected-2,2,2-trichloromethylcarbinols and 2,2,2-trichloromethylcarbinols 1 was developed that employs the in situ generation and reaction of trimethyl(trichloromethyl)silane (CCl3-TMS). The procedure avoids the exposure of the carbonyl compounds to the strongly basic conditions typically used for this transformation and also avoids isolation of the difficult-to-handle CCl3-TMS. This procedure was applied to diastereoselective trichloromethyl additions to 2-substituted 4-piperidinones and to reactions with a variety of structurally diverse aldehydes and ketones.

  DOI：

  10.1021/jo3001063

文献信息

• An improved preparation and a new application of trichloromethylcarbinols from enolizable ketones
  作者：Jing Li、Brenden Derstine、Takahiro Itoh、Jaume Balsells

  DOI：10.1016/j.tetlet.2014.03.118

  日期：2014.5

  We report an improved method for the preparation of trichloromethylcarbinols from enolizable ketones. Trichloromethylcarbinols were obtained in good to excellent yields by using of a combination of CHCl3, n-BuLi, and chlorotitanium (IV) triisopropoxide. Hydrolysis of the trichloromethylcarbinol to an alpha,beta-unsaturated ester was also explored. (C) 2014 Elsevier Ltd. All rights reserved.