1-propylcyclohex-2-en-1-ol | 115834-54-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-propylcyclohex-2-en-1-ol
• 英文别名: 1-propylcyclohex-2-enol；1-n-propylcyclohex-2-enol
• CAS: 115834-54-3
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: SGKABVNEOFLQPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-propylcyclohex-2-en-1-ol 在 laccase from Trametes versicolor 、 氧气 、 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate 作用下， 以 二甲基亚砜 为溶剂， 30.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以97%的产率得到3-丙基环己-2-烯-1-酮
  参考文献：
  名称：

  叔丁醇的化学酶促氧化重排：合成应用并将其集成到级联过程中。

  摘要：

  化学-酶促催化体系，由包括波比茨的盐和漆酶的变色栓菌，允许在水性介质中的氧气气氛下将环内烯丙基叔醇[1,3]-氧化重排成相应的烯酮。在大多数情况下，产率是定量的，特别是对于在侧链上没有吸电子基团（EWG）的环戊2烯1醇或环己2烯1醇底物。相反，通过使用固定的漆酶制剂，在乙腈中进行在侧链带有EWG的大环烯醇或叔醇的转座。脱氢Jasmone®，脱氢Hedione®，脱氢麝香酮和其它香味前体直接与此方法制得，而合成路线的开发是为了容易地转化环戊烯酮衍生物进反式Magnolione®和脱氢Magnolione® 。还测试了环外烯丙基醇的重排，并观察到动态动力学拆分：合成了具有（E）-构型和高非对映异构体过量的α，β-不饱和酮。最后，将2,2,6,6-四甲基-1-哌啶四氟硼酸（TEMPO + BF 4 -）/漆酶催化的氧化重排与烯还原酶/醇脱氢酶级联过程结合在一起，进行一锅三步合成在两种情况下均具有

  DOI：

  10.1002/adsc.201800299
• 作为产物：
  描述：

  2-环己烯-1-酮 、 propyllithium 在 lithium bromide 、 氯化铵 作用下， 以 2-甲基四氢呋喃 、 乙醚 、 水 为溶剂， 反应 2.0h， 以95%的产率得到1-propylcyclohex-2-en-1-ol
  参考文献：
  名称：

  Highly regioselective control of 1,2-addition of organolithiums to α,β-unsaturated compounds promoted by lithium bromide in 2-methyltetrahydrofuran: a facile and eco-friendly access to allylic alcohols and amines

  摘要：

  Very high regioselective 1,2-addition of organolithiums to alpha,beta-unsaturated carbonyl-like compounds (ketones, aldehydes, and imines) in the presence of LiBr was achieved by carrying out reactions in the sustainable solvent 2-methyltetrahydrofuran. Excellent yields (in isolated product) of allylic alcohols and allylic amines were recovered under a simple experimental procedure at 0 degrees C. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.067

文献信息

• The preparation of lithium organocuprates from various Cu(I) salts
  作者：Steven H. Bertz、Charles P. Gibson、Gary Dabbagh

  DOI：10.1016/s0040-4039(00)96477-3

  日期：1987.1

  Various Cu(I) salts have been tested as precursors for organocuprates in side-by-side comparisons under controlled conditions. CuCN and CuBr·SMe2 appear to be superior to CuI, CuBr, and CuCl. CuSCN and CuOTf are also good precursors in some circumstances.

  在受控条件下进行并排比较时，已测试了各种Cu（I）盐作为有机铜酸盐的前体。CuCN和CuBr·SMe 2似乎优于CuI，CuBr和CuCl。在某些情况下，CuSCN和CuOTf也是良好的前体。
• BERTZ, STEVEN H.;GIBSON, CHARLES P.;DABBAGH, GARY, TETRAHEDRON LETT., 28,(1987) N 37, 4251-4254
  作者：BERTZ, STEVEN H.、GIBSON, CHARLES P.、DABBAGH, GARY

  DOI：——

  日期：——
• (2-HYDROXY)ETHYL-THIOUREAS USEFUL AS MODULATORS OF ALPHA2B ADRENERGIC RECEPTORS
  申请人：Allergan, Inc.

  公开号：EP1381593A2

  公开（公告）日：2004-01-21
• [EN] (2-HYDROXY)ETHYL-THIOUREAS USEFUL AS MODULATORS OF ALPHA2B ADRENERGIC RECEPTORS<br/>[FR] (2-HYDROXY)ETHYLTHIOUREAS UTILES EN TANT QUE MODULATEURS DES RECEPTEURS ADRENERGIQUES ALPHA2B
  申请人：ALLERGAN INC

  公开号：WO2002068384A2

  公开（公告）日：2002-09-06

  Compounds of formula (i) and of formula (ii), wherein the symbols have the meaning disclosed in the claims, specifically or selectively modulate α2A adrenergic receptors and as such are useful for alleviating chronic pain and allodynia and have no or only minimal cardiovascular and/or sedatory activity. The invention also relates to a method of activating α2B or α2C adrenergic receptors in a mammal by administering a compound that has α2Bor α2C adrenergic receptor activity and has no significant α2A agonist activity.
• Highly regioselective control of 1,2-addition of organolithiums to α,β-unsaturated compounds promoted by lithium bromide in 2-methyltetrahydrofuran: a facile and eco-friendly access to allylic alcohols and amines
  作者：Vittorio Pace、Laura Castoldi、Pilar Hoyos、José Vicente Sinisterra、Massimo Pregnolato、José Ma Sánchez-Montero

  DOI：10.1016/j.tet.2011.01.067

  日期：2011.4

  Very high regioselective 1,2-addition of organolithiums to alpha,beta-unsaturated carbonyl-like compounds (ketones, aldehydes, and imines) in the presence of LiBr was achieved by carrying out reactions in the sustainable solvent 2-methyltetrahydrofuran. Excellent yields (in isolated product) of allylic alcohols and allylic amines were recovered under a simple experimental procedure at 0 degrees C. (C) 2011 Elsevier Ltd. All rights reserved.