8-hydroxyoctyl benzoate | 162843-89-2

• 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: 8-hydroxyoctyl benzoate
• 英文别名: 1,8-Octanediol, 1-benzoate
• CAS: 162843-89-2
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: UMJKUPRCJPGQKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-hydroxyoctyl benzoate 在 草酰氯 、 盐酸二甲胺 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 benzoic acid 7-formyl-oct-7-enyl ester
  参考文献：
  名称：

  Evaluation of possible intramolecular [4+2] cycloaddition routes for assembling the central tetracyclic core of the potent marine antiinflammatory agent mangicol A

  摘要：

  A plan for enantioselective construction of the mangicol A framework by means of intramolecular Diels-Alder cycloaddition is outlined. First to be assembled is the enantiopure cyclopentenecarboxylic acid 16. Of the several approaches targeting the 1,3-diene component 56, only that involving palladium-catalyzed enyne cyclization proved successful. Following the coupling of 16 to 56, we were unable to bring about any detectable level of (4 pi+2 pi) cycloaddition. Activation of the diene by incorporation of an OSiEt3 substituent on a terminal sp(2)-hybridized center likewise proved unsuccessful. Further facilitation was sought in the form of cyclopentenonecarboxylate 66. However, thermal activation, Lewis acid catalysis, and high-pressure conditions proved ineffective and did not lead to C-C bond formation. These studies serve to underscore the extent to which steric complications can complicate matters and the extent to which they must be skirted to arrive at the title compound. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.096
• 作为产物：
  描述：

  benzoic acid 9-oxo-nonyl ester 在 acetylacetonatodicarbonylrhodium(l) 、 三氟甲磺酸 、 一氧化碳 、 N-(5-diphenylphosphanylpyrrole-2-carbonyl)guanidine 、 氢气 作用下， 以 二氯甲烷 为溶剂， 40.0 ℃ 、2.0 MPa 条件下， 反应 20.0h， 以99%的产率得到8-hydroxyoctyl benzoate
  参考文献：
  名称：

  醛加氢和串联加氢甲酰化-加氢的超分子催化剂

  摘要：

  超分子催化剂可以实现醛的化学选择性还原和末端烯烃的串联加氢甲酰化-氢化反应，这种超分子催化剂可以通过一种新颖的机理起作用，包括通过氢键和随后的金属-配体双功能加氢进行底物活化（参见方案）。

  DOI：

  10.1002/anie.200903620

文献信息

• Polystyrene-supported GaCl3: A new, highly efficient and recyclable heterogeneous Lewis acid catalyst for tetrahydropyranylation of alcohols and phenols
  作者：Ali Rahmatpour

  DOI：10.1016/j.poly.2012.06.063

  日期：2012.8

  highly chemoselective method for tetrahydropyranylation of alcohols and phenols with 3,4-dihydro-2H-pyran (DHP) in the presence of polystyrene-supported gallium trichloride (PS/GaCl3) as a highly active and reusable heterogeneous Lewis acid catalyst at room temperature is presented. In this catalytic system, primary, secondary and tertiary alcohols, as well as phenols, were converted to the corresponding

  在聚苯乙烯负载的三氯化镓（PS / GaCl 3）存在下，用3,4-二氢-2 H-吡喃（DHP）对醇和酚进行四氢吡喃基化的一种新的，简单且高度化学选择性的方法）是在室温下具有高活性和可重复使用的非均相路易斯酸催化剂。在该催化体系中，伯，仲和叔醇以及苯酚以短的反应时间和高收率转化为相应的四氢吡喃基（THP）醚。异质催化剂在吡喃基化反应中具有高可重复使用性和稳定性，并且被回收了数次，其活性损失可忽略不计且催化剂浸出可忽略不计，并且也不需要再生。该方法对对称二醇的单四氢吡喃基化反应也显示出良好的化学选择性。
• Acetonyltriphenylphosphonium Bromide (ATPB): A Versatile Reagent for the Acylation of Alcohols, Phenols, Thiols and Amines and for 1,1-Diacylation of Aldehydes under Solvent-Free Conditions
  作者：Abu T. Khan、Lokman H. Choudhury、Subrata Ghosh

  DOI：10.1002/ejoc.200500066

  日期：2005.7

  A wide variety of alcohols, phenols, amines and thiols may easily be converted into the corresponding acetate derivatives by treatment with acetic anhydride (1.5–2.0 equivalents) in the presence of acetonyltriphenylphosphonium bromide (ATPB; 5 mol %) in good yields at room temperature. With the same precatalyst, both aliphatic and aromatic aldehydes can also be transformed into the corresponding gem-diacetates

  在室温下，在丙酮基三苯基溴化鏻（ATPB；5 mol%）存在下，通过用乙酸酐（1.5-2.0 当量）处理，可以很容易地将多种醇、酚、胺和硫醇转化为相应的乙酸衍生物. 使用相同的预催化剂，脂肪醛和芳香醛也可以在回流条件下转化为相应的双乙酸酯。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Protecting-group-free synthesis of hydroxyesters from amino alcohols
  作者：Guillaume Reynard、Eve-Marline Joseph-Valcin、Hélène Lebel

  DOI：10.1039/d0cc03242e

  日期：——

  The synthesis of hydroxyesters from carboxylic acids and unprotected amino alcohols in both continuous flow and batch processes is reported. The formation of a transient diazonium species with a dinitrite reagent is key in this transformation. The reaction conditions are compatible with a variety of functional groups.

  报道了在连续流动和间歇过程中由羧酸和未保护的氨基醇合成羟基酯的方法。用亚硝酸盐试剂形成瞬态重氮物质是该转化的关键。反应条件与各种官能团相容。
• Polystyrene-Gallium Trichloride Complex: A Mild, Highly Efficient, and Recyclable Polymeric Lewis Acid Catalyst for Chemoselective Silylation of Alcohols and Phenols with Hexamethyldisilazane
  作者：Ali Rahmatpour、Ali Vakili、Setare Azizian

  DOI：10.1002/hc.21109

  日期：2013.11

  (HMDS) for the efficient silylation of alcohols and phenols at room temperature. In this heterogeneous catalytic system, primary, secondary, and tertiary alcohols as well as phenols were converted to their corresponding trimethylsilyl ethers with short reaction times and high yields under mild reaction conditions. The heterogenized catalyst is of high reusability and stability in the silylation reactions

  聚苯乙烯负载的三氯化镓 (PS/GaCl3) 作为一种高活性且可重复使用的多相路易斯酸，可有效激活六甲基二硅氮烷 (HMDS)，从而在室温下有效地将醇和酚进行甲硅烷基化。在这种多相催化体系中，伯醇、仲醇和叔醇以及酚类在温和的反应条件下以短反应时间和高产率转化为相应的三甲基甲硅烷基醚。该多相催化剂在甲硅烷基化反应中具有较高的重复使用性和稳定性，可多次回收，其活性损失或催化剂浸出可忽略不计，且无需再生。值得注意的是，该方法可用于不同醇和酚的高产率化学选择性硅烷化。
• Elaboration of the ether cleaving ability and selectivity of the classical Pearlman's catalyst [Pd(OH)2/C]: concise synthesis of a precursor for a myo-inositol pyrophosphate
  作者：Alson Mart、Mysore S. Shashidhar

  DOI：10.1016/j.tet.2012.09.016

  日期：2012.11

  The cleavage of propargyl, allyl, benzyl, and PMB ethers by Pd(OH)2/C can be tuned in that order, by varying the reaction conditions. Other moieties such as C–C double bonds, esters, trityl ether, p-bromo and p-nitrobenzyl ethers are stable to these reaction conditions. Cleavage of allyl ethers can be made catalytic by using 1:1 mixture of Pd(OH)2/C and Pd/C. The synthetic potential of the selective

  可以通过改变反应条件来按顺序调节炔丙基，烯丙基，苄基和PMB醚被Pd（OH）2 / C的裂解。其他部分，如CC双键，酯，三苯甲基醚，对溴和对硝基苄基醚对这些反应条件稳定。可以通过使用Pd（OH）2 / C和Pd / C的1：1混合物催化裂解烯丙基醚。基本上在中性条件下，Pd（OH）2 / C的选择性醚裂解能力的合成潜力已通过有效合成用于制备肌醇焦磷酸盐衍生物的前体得到了证明。