2-(hydroxymethyl)-bicyclo[2.2.1]hept-5-ene-2-ethanol | 160189-62-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(hydroxymethyl)-bicyclo[2.2.1]hept-5-ene-2-ethanol
• 英文别名: 2-[2-(Hydroxymethyl)-2-bicyclo[2.2.1]hept-5-enyl]ethanol
• CAS: 160189-62-8
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: VXLYAWXNRVVASY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  2-(hydroxymethyl)-bicyclo[2.2.1]hept-5-ene-2-ethanol 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 吡啶 、 sodium hydride 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 为溶剂， 反应 31.0h， 生成 methyl 6-acetoxy-2-(methoxycarbonyl)-4-methylenehexanoate
  参考文献：
  名称：

  Total Synthesis and Stereochemistry of Alternaric Acid

  摘要：

  Determination of the stereochemistry and the total synthesis of alternaric acid 1 has been achieved. The stereostructure of 1 has been elucidated by stereoselective synthesis of four diastereoisomers of the C(9)-C(14) fragment 6, which had been obtained as a degradation product during structural studies. Key reactions of the total synthesis of 1 include the Julia olefination of tertiary aldehyde 6 and phenylsulfone 7 and novel one-pot construction of 3-acyl-4-hydroxy-5,6-dihydro-2-pyrone via Fries-type rearrangement of the O-enol acyl group of beta-keto-delta-valerolactone toward the a-position of the delta-lactone. The absolute configuration of alternaric acid has been shown to be that illustrated in structure 1. The modified Fries-type rearrangement method has also been extended to the synthesis of some other compounds containing a tricarbonylmethane structure.

  DOI：

  10.1021/jo00096a016
• 作为产物：
  描述：

  衣康酸二甲酯 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 、 苯 为溶剂， 反应 6.5h， 生成 2-(hydroxymethyl)-bicyclo[2.2.1]hept-5-ene-2-ethanol
  参考文献：
  名称：

  Total Synthesis and Stereochemistry of Alternaric Acid

  摘要：

  Determination of the stereochemistry and the total synthesis of alternaric acid 1 has been achieved. The stereostructure of 1 has been elucidated by stereoselective synthesis of four diastereoisomers of the C(9)-C(14) fragment 6, which had been obtained as a degradation product during structural studies. Key reactions of the total synthesis of 1 include the Julia olefination of tertiary aldehyde 6 and phenylsulfone 7 and novel one-pot construction of 3-acyl-4-hydroxy-5,6-dihydro-2-pyrone via Fries-type rearrangement of the O-enol acyl group of beta-keto-delta-valerolactone toward the a-position of the delta-lactone. The absolute configuration of alternaric acid has been shown to be that illustrated in structure 1. The modified Fries-type rearrangement method has also been extended to the synthesis of some other compounds containing a tricarbonylmethane structure.

  DOI：

  10.1021/jo00096a016

文献信息

• Norbornane based cycloaliphatic compounds containing nitrile groups
  申请人：Allgeier Martin Alan

  公开号：US20050159614A1

  公开（公告）日：2005-07-21

  This invention relates to novel norborane nitrile derivatives, and corresponding methods for making the same using hydrocyanation reactions.

  这项发明涉及新颖的去甲杂环戊烷腈衍生物，以及利用氢氰化反应制备它们的相应方法。
• Novel tetrahydrofuran compounds having alicyclic structure
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：US20020183529A1

  公开（公告）日：2002-12-05

  Tetrahydrofuran compounds of formula (1) wherein the broken line represents a single bond, a divalent organic group, or a structure in which the alicyclic structure in the form of norbornene or tetracyclo[4.4.0.1 2,5 .1 7,10 ]dodecene and the tetrahydrofuran cyclic structure share one or two constituent carbon atoms, and k is 0 or 1 are novel and useful as monomers to form base resins for use in chemically amplified resist compositions adapted for micropatterning lithography. 1

  公式（1）中的四氢呋喃化合物，其中断裂的线表示单键，二价有机基团或环状结构，该环状结构以诺博尔烯或四环[4.4.0.12,5.17,10]十二烯的形式存在，并且四氢呋喃环状结构共享一个或两个构成碳原子，k为0或1，是一种新颖且有用的单体，用于形成基础树脂，用于化学增强型抗蚀剂组合物，适用于微细图案印刷。
• Heterotricyclic compounds, processes for their production and pharmaceutical compositions containing them
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0006283A1

  公开（公告）日：1980-01-09

  A compound of the formula: wherein A, is a single bond or a C1-C5 alkylene group bonding at the 2- or 3-position, A2 is a C1-C4 alkylene group, A3 is a single bond or a C1-C3 alkylene group, X-Y is -O-CH2- -O-CO- or -SOn-CH2- and B is a carboxy group, a C2-C5 alkoxycarbonyl group, a cyano group, a hydroxy group, a C2-C5 acyloxy group, a halogen group, a carbamoyl group of the formula: or an amino group of the formula: The compounds of the invention are useful as antiviral agents against, for example, influenza virus and herpes simplex virus.

  式中的化合物： 其中 A 是单键或键合在 2 位或 3 位的 C1-C5 亚烷基，A2 是 C1-C4 亚烷基，A3 是单键或 C1-C3 亚烷基，X-Y 是 -O-CH2- -O-CO- 或 -SOn-CH2- 和 B 是羧基、C2-C5 烷氧基羰基、氰基、羟基、C2-C5 乙酰氧基、卤素基、式中的氨基甲酰基： 或式中的氨基： 本发明的化合物可用作抗病毒剂，例如抗流感病毒和单纯疱疹病毒。
• Total synthesis of alternaric acid
  作者：Hiroyasu Tabuchi、Taisuke Hamamoto、Shokyo Miki、Tsuyoshi Tejima、Akitami Ichihara

  DOI：10.1016/s0040-4039(00)77605-2

  日期：1993.4

  A total synthesis of alternaric acid (1) has been achieved. Key reactions include the Julia olefination of tertiary aldehyde 4 and phenylsulfone 5, and novel one-pot construction of 3-acyl-4-hydroxy-5,6-dihydropyrone via Fries type rearrangement of O-enolacyl group of beta-keto-delta-valerolactone toward alpha-position of the delta-lactone. The absolute configuration of alternaric acid has been shown to be that illustrated in structure 1.
• NORBORNANE BASED CYCLOALIPHATIC COMPOUNDS CONTAINING NITRILE GROUPS
  申请人：INVISTA NORTH AMERICA S.A R.L.

  公开号：EP1706374A2

  公开（公告）日：2006-10-04