1-methoxy-5-phenyl-3-pentanol | 785803-80-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-methoxy-5-phenyl-3-pentanol
• 英文别名: 1-Methoxy-5-phenylpentan-3-ol
• CAS: 785803-80-7
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: KSURIDBUEXOPPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methoxy-5-phenyl-3-pentanol 在 甲酸 、 氯磺酰异氰酸酯 作用下， 以 2,4-滴二甲胺盐 、 乙腈 为溶剂， 以73%的产率得到1-methoxy-5-phenylpentan-3-yl sulfamate
  参考文献：
  名称：

  A mechanistic analysis of the Rh-catalyzed intramolecular C–H amination reaction

  摘要：

  A detailed mechanistic investigation of the intramolecular dirhodium tetracarboxylate-catalyzed sulfamate ester C-H amination reaction is presented. These studies provide support for the formation of a sulfamate-derived iminoiodinane, which reacts rapidly with the rhodium catalyst to generate a nitrenoid-type oxidant. Reactivity patterns, Hammett analysis, kinetic isotope measurement, and a cyclopropane clock experiment are indicative of a concerted, asynchronous transition structure in the product-determining C-H insertion event. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2008.11.073
• 作为产物：
  描述：

  1-tert-butyldimethylsilyloxy-2-(5-phenyl-1-hydroxy-3-pentyloxy)-1,2-diphenylethane 在 ammonium cerium(IV) nitrate 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 甲苯 、 乙腈 为溶剂， 反应 48.5h， 生成 1-methoxy-5-phenyl-3-pentanol
  参考文献：
  名称：

  Mild and Efficient Removal of Hydroxyethyl Unit from 2-Hydroxyethyl Ether Derivatives Leading to Alcohols

  摘要：

  CAN is a good reagent for the transformation of 2-hydroxyethyl ether units to alcohols. Significantly, many functional groups can tolerate the reaction conditions, although they do not survive under many previously reported removal conditions. The reaction mechanism is clarified.

  DOI：

  10.1021/ol051135i

文献信息

• Cerium ammonium nitrate (CAN) for mild and efficient reagent to remove hydroxyethyl units from 2-hydroxyethyl ethers and 2-hydroxyethyl amines
  作者：Hiromichi Fujioka、Hideki Hirose、Yusuke Ohba、Kenichi Murai、Kenji Nakahara、Yasuyuki Kita

  DOI：10.1016/j.tet.2006.11.004

  日期：2007.1

  Cerium ammonium nitrate (CAN) removed hydroxyethyl units from 2-hydroxyethyl ethers and 2-hydroxyethyl amines to produce alcohols and amines in good yields. Especially, removal of the 2-hydroxyethyl ethers from C-2-symmetric diols, chiral 2,3-butanediol and chiral hydrobenzoin, was very useful for asymmetric syntheses using C-2-symmetric diols. The reactions using dual abilities of CAN, i.e., the ability for removal of the 2-hydroxyethyl unit and the ability for acetal hydrolysis by a single electron transfer, were also achieved Successfully. The reaction conditions were very mild and efficient, and many functional groups, which can be affected under normal conditions, were unaffected during the reaction. (c) 2006 Published by Elsevier Ltd.
• Rh-Catalyzed Amination of Ethereal CαH Bonds: A Versatile Strategy for the Synthesis of Complex Amines
  作者：Kristin Williams Fiori、James J. Fleming、Justin Du Bois

  DOI：10.1002/anie.200460791

  日期：2004.8.20
• Mild and Efficient Removal of Hydroxyethyl Unit from 2-Hydroxyethyl Ether Derivatives Leading to Alcohols
  作者：Hiromichi Fujioka、Yusuke Ohba、Hideki Hirose、Kenichi Murai、Yasuyuki Kita

  DOI：10.1021/ol051135i

  日期：2005.7.1

  CAN is a good reagent for the transformation of 2-hydroxyethyl ether units to alcohols. Significantly, many functional groups can tolerate the reaction conditions, although they do not survive under many previously reported removal conditions. The reaction mechanism is clarified.
• A mechanistic analysis of the Rh-catalyzed intramolecular C–H amination reaction
  作者：Kristin Williams Fiori、Christine G. Espino、Benjamin H. Brodsky、J. Du Bois

  DOI：10.1016/j.tet.2008.11.073

  日期：2009.4

  A detailed mechanistic investigation of the intramolecular dirhodium tetracarboxylate-catalyzed sulfamate ester C-H amination reaction is presented. These studies provide support for the formation of a sulfamate-derived iminoiodinane, which reacts rapidly with the rhodium catalyst to generate a nitrenoid-type oxidant. Reactivity patterns, Hammett analysis, kinetic isotope measurement, and a cyclopropane clock experiment are indicative of a concerted, asynchronous transition structure in the product-determining C-H insertion event. (C) 2008 Published by Elsevier Ltd.