2-环戊基丙醇 | 36794-65-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-环戊基丙醇
• 英文名称: 2-Cyclopentyl-propanol-(1)
• 英文别名: 2-Cyclopentylpropan-1-ol
• CAS: 36794-65-7
• 化学式: C₈H₁₆O
• 分子量: 128.214
• InChiKey: CAUGGFPRZKOLJT-UHFFFAOYSA-N

物化性质

• 沸点：
  65-67 °C(Press: 2.5 Torr)
• 密度：
  0.926±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  2-环戊基丙醇 在 sodium hydroxide 、 potassium permanganate 作用下， 生成 2-cyclopentylpropanoic acid
  参考文献：
  名称：

  联用环氧氯丙烷和环戊二烯基钠

  摘要：

  环氧氯丙烷与环戊二烯基萘在约90％的澳大利亚生产的产品中存在，但仍可与2-环戊二烯基-烯丙醇类化合物混合使用。

  DOI：

  10.1002/hlca.19620450435
• 作为产物：
  描述：

  2-环戊基丙酸甲酯 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 环己烯 为溶剂， 生成 2-环戊基丙醇
  参考文献：
  名称：

  由瞬态配体实现的脂肪醛的催化 C-H 芳基化

  摘要：

  脂肪醛的直接芳基化是通过 Pd 催化的 sp3 CH 键官能化在 3-氨基丙酸作为瞬时导向基团存在下建立的。该反应显示出优异的官能团兼容性和化学选择性，其中实现了对甲基的未活化 β-CH 键功能化的主要偏好。此外，未活化的二级 sp3 碳的 CH 键也可以被功能化。脂肪醛的极端流行和重要性将导致这种新方法在有机化学和医学科学中的广泛应用。

  DOI：

  10.1021/jacs.6b08478

文献信息

• [EN] PROCESS FOR THE PREPARATION OF A beta 3-AGONIST<br/>[FR] PROCEDE DE PREPARATION D'UN AGONISTE DE beta 3
  申请人：MERCK & CO., INC.

  公开号：WO1997034880A1

  公开（公告）日：1997-09-25

  (EN) 3-Cyclopentylpropylazide and $i(p)-chlorosulfonylphenyl-isocyanate undergo cycloaddition to form 1-cyclopropyl-4-($i(p)-chloro-sulfonylphenyl) tetrazone-5-one, a key intermediate in the synthesis of an important $g(b)3-agonist.(FR) 3-cyclopentylpropylazide et $i(p)-chlorosulfonylphényl-isocyanate subissent un apport cyclique, de sorte que du 1-cyclopropyle-4-($i(p)-chlorosulfonylphényle)tétrazone-5-one soit produit, intermédiaire indispensable dans la synthèse d'un agoniste important de $g(b)3.

  3-环戊基丙基叠氮化物和$p$-氯磺酰基苯基异氰酸酯发生环加成反应，形成1-环丙基-4-($p$-氯磺酰基苯基)四唑-5-酮，是合成重要的$g(b)3-激动剂的关键中间体。
• THE SYNTHESIS OF CERTAIN ACIDS DERIVED FROM CYCLOPENTANE
  作者：WERNER HERZ

  DOI：10.1021/jo01365a017

  日期：1955.8
• Rao, R. R.; Sarkar, Rina; Bhattacharya, Sukla, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 939 - 946
  作者：Rao, R. R.、Sarkar, Rina、Bhattacharya, Sukla、Mukherjee, M. N.

  DOI：——

  日期：——
• Total synthesis of spatane diterpenes: the tricyclic nucleus
  作者：Robert G. Salomon、Navzer D. Sachinvala、Subhas Roy、Basudeb Basu、Swadesh R. Raychaudhuri、Donald B. Miller、Ram B. Sharma

  DOI：10.1021/ja00008a043

  日期：1991.4

  A convergent, stereocontrolled construction of the cis,anti,cis-tricyclo[5.3.0.0(2,6)]decane nucleus of spatane diterpenes was achieved by 2-pi + 2-pi photocycloaddition of 2-cyclopenten-1-one, as an A-ring precursor, with a carbonyl-masked derivative of 6-methylbicyclo[2.2.1]hept-5-en-2-one as a temporarily bridged C-ring precursor. By design, the temporary bridge assures the correct stereochemical relationship between the B-ring stereocenters and the C-ring hydroxyl substituent that is present in latent form in the oxoethano bridge. Serendipitously, the bridge also fosters a favorable orientation of the photocycloaddition that contrasts with the nonselective 2-pi + 2-pi-photocycloadditions of unbridged 1-methylcyclopentenes with 2-cyclopenten-1-one. Wittig methylenation of the A-ring carbonyl in photoproduct 24 followed by hydrolysis to 25 and catalytic hydrogenation introduces a methyl group at position 1 with a 10:1 preference for the requisite stereochemistry in 26. Even higher stereoselectivity was achieved by SO2-promoted isomerization of the exocyclic C=C bond in 25 to an endocyclic disposition in 29 prior to catalytic hydrogenation. Johnson's sulfoximine method is especially effective for resolution of ketone 29. The oxoethano bridge in ketone 26n is oxidized rapidly but nonregioselectively by an H2SO4-catalyzed reaction with peracetic acid, producing a 57:43 mixture of 14 and 34. Regioselective generation of the desired lactone 14 could be accomplished by a much slower oxidation with peracetic acid and no added H2SO4. The necessary configuration at position 7 in 49 was generated stereoselectively by a novel homoallylic hydroxyl-directed, pseudointramolecular delivery of hydride to the methylenemalonic ester in the precursor 48. Conversion of the malonic ester moiety in 49 into an allylic alcohol was accomplished in 92% overall yield by monosaponification, decarboxylative condensation with formaldehyde and reduction of the resulting acrylic ester with i-Bu2AlH. Selective oxidation of the allylic hydroxyl followed by acetylation delivered acetate (+)-11a, which is identical with an oxidative degradation product from spatane diterpenes.
• SALOMON, ROBERT G.;SACHINVALA, NAVZER D.;ROY, SUBHAS;BASU, BASUDEB;RAYCHA+, J. AMER. CHEM. SOC., 113,(1991) N, C. 3085-3095
  作者：SALOMON, ROBERT G.、SACHINVALA, NAVZER D.、ROY, SUBHAS、BASU, BASUDEB、RAYCHA+

  DOI：——

  日期：——