3-hydroxymethylcyclohex-2-en-1-ol | 218129-85-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroxymethylcyclohex-2-en-1-ol
• 英文别名: 3-(Hydroxymethyl)cyclohex-2-en-1-ol
• CAS: 218129-85-2
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: QWKDJMHFHUKBIT-UHFFFAOYSA-N

物化性质

• 沸点：
  263.7±28.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxymethylcyclohex-2-en-1-ol 在 吡啶 、 4-二甲氨基吡啶 、 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 3-(Trityloxymethyl)cyclohex-2-en-1-one
  参考文献：
  名称：

  Studies on the substituted 3-aminopropan-1-ol motif of lycoctonine class norditerpenoid alkaloids: A novel route to 3-hydroxymethylcyclohex-2-enone

  摘要：

  Pursuing our interest in methyllycaconitine (MLA), we have designed a synthetic route to substituted ring-A of lycoctonine class norditerpenoid alkaloids. A novel synthesis of 3-hydroxymethylcyclohex-2-enone has been achieved starting from cyclohex-2-enone. Key reactions are: 1,2-addition of 1,3-dithiane followed by allylic rearrangement, 1,4-hydrocyanation, Wittig reaction and conversion into the substituted N-ethyl-3-aminopropan-1-ol motif of these neopentyl-like alcohols. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01857-7
• 作为产物：
  描述：

  3-((phenylthio)methyl)-2-cyclohexenone 在 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 间氯过氧苯甲酸 、 三氟乙酸酐 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 9.33h， 生成 3-hydroxymethylcyclohex-2-en-1-ol
  参考文献：
  名称：

  Different Reaction Modes for the Oxidative Dimerization of Epoxyquinols and Epoxyquinones. Importance of Intermolecular Hydrogen-Bonding

  摘要：

  An oxidative dimerization reaction, involving the three successive steps of oxidation, 6pi-electrocyclization, and Diels-Alder reaction, has been experimentally and theoretically investigated for the three 2-alkenyl-3-hydroxymethyl-2-cyclohexen-1-one derivatives epoxyquinol 3, epoxyquinone 6, and cyclohexenone 10. Of the sixteen possible modes of the oxidation/6pi-electrocylization/Diels-Alder reaction cascade for the epoxyquinone 6, and eight for the cyclohexenone 10, only the endo-anti(epoxide)-anti(Me)-hetero and endo-anti(Me)-hetero modes are, respectively, observed, while both endo-anti(epoxide)-anti(Me)-hetero and exo-anti(epoxide)-anti(Me)-homo reaction modes occur with the epoxyquinol 3. Intermolecular hydrogen-bonding is found to be the key cause of formation of both epoxyquinols A and B with 3, although epoxyquinone 6 and cyclohexenone 10 both gave selectively only the epoxyquinol A-type product. In the dimerization of epoxyquinol 3, two monomer 2H-pyrans 5 interact with each other to afford intermediate complex 28 or 29 stabilized by hydrogen-bonding, from which Diels-Alder reaction proceeds. Theoretical calculations have also revealed the differences in the reaction profiles of epoxyquinone 6 and cyclohexenone 10. Namely, the rate-determining step of the former is the Diels-Alder reaction, while that of the latter is the 6pi-electrocyclization.

  DOI：

  10.1021/jo0355303

文献信息

• SUBSTITUTED FLUOROETHYL UREAS AS ALPHA 2 ADRENERGIC AGENTS
  申请人：Chow Ken

  公开号：US20080255239A1

  公开（公告）日：2008-10-16

  Therapeutic compounds, and methods, compositions, and medicaments related thereto are disclosed herein.

  本文揭示了治疗化合物、方法、组合物和相关药物。
• US7598417B2
  申请人：——

  公开号：US7598417B2

  公开（公告）日：2009-10-06
• Different Reaction Modes for the Oxidative Dimerization of Epoxyquinols and Epoxyquinones. Importance of Intermolecular Hydrogen-Bonding
  作者：Mitsuru Shoji、Hiroki Imai、Isamu Shiina、Hideaki Kakeya、Hiroyuki Osada、Yujiro Hayashi

  DOI：10.1021/jo0355303

  日期：2004.3.1

  An oxidative dimerization reaction, involving the three successive steps of oxidation, 6pi-electrocyclization, and Diels-Alder reaction, has been experimentally and theoretically investigated for the three 2-alkenyl-3-hydroxymethyl-2-cyclohexen-1-one derivatives epoxyquinol 3, epoxyquinone 6, and cyclohexenone 10. Of the sixteen possible modes of the oxidation/6pi-electrocylization/Diels-Alder reaction cascade for the epoxyquinone 6, and eight for the cyclohexenone 10, only the endo-anti(epoxide)-anti(Me)-hetero and endo-anti(Me)-hetero modes are, respectively, observed, while both endo-anti(epoxide)-anti(Me)-hetero and exo-anti(epoxide)-anti(Me)-homo reaction modes occur with the epoxyquinol 3. Intermolecular hydrogen-bonding is found to be the key cause of formation of both epoxyquinols A and B with 3, although epoxyquinone 6 and cyclohexenone 10 both gave selectively only the epoxyquinol A-type product. In the dimerization of epoxyquinol 3, two monomer 2H-pyrans 5 interact with each other to afford intermediate complex 28 or 29 stabilized by hydrogen-bonding, from which Diels-Alder reaction proceeds. Theoretical calculations have also revealed the differences in the reaction profiles of epoxyquinone 6 and cyclohexenone 10. Namely, the rate-determining step of the former is the Diels-Alder reaction, while that of the latter is the 6pi-electrocyclization.
• Studies on the substituted 3-aminopropan-1-ol motif of lycoctonine class norditerpenoid alkaloids: A novel route to 3-hydroxymethylcyclohex-2-enone
  作者：Xavier Doisy、Ian S. Blagbrough、Noel F. Thomas、Barry V.L. Potter

  DOI：10.1016/s0040-4039(98)01857-7

  日期：1998.11

  Pursuing our interest in methyllycaconitine (MLA), we have designed a synthetic route to substituted ring-A of lycoctonine class norditerpenoid alkaloids. A novel synthesis of 3-hydroxymethylcyclohex-2-enone has been achieved starting from cyclohex-2-enone. Key reactions are: 1,2-addition of 1,3-dithiane followed by allylic rearrangement, 1,4-hydrocyanation, Wittig reaction and conversion into the substituted N-ethyl-3-aminopropan-1-ol motif of these neopentyl-like alcohols. (C) 1998 Elsevier Science Ltd. All rights reserved.