5-(2-propenyloxy)pentanol | 139551-67-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(2-propenyloxy)pentanol
• 英文别名: 5-O-allyl-1-pentanol；5-allyloxypentanol；allyloxy-5-pentanol；1-Pentanol, 5-(2-propenyloxy)-；5-prop-2-enoxypentan-1-ol
• CAS: 139551-67-0
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: POHJXBUHHVFIEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(2-propenyloxy)pentanol 在 Jones reagent 作用下， 以 丙酮 为溶剂， 生成 5-(allyloxy)pentanoic acid
  参考文献：
  名称：

  Efficient Medium Ring Size Bromolactonization Using a Sulfur-Based Zwitterionic Organocatalyst

  摘要：

  Catalytic bromolactonization of long-chain olefinic acids resulting in the efficient synthesis of medium-sized lactones is reported using a zwitterionic catalyst and stoichiometric N-bromosuccinimide halogen source. The reaction was found to be more efficient at 0 degrees C than at room temperature, which could be attributed to the temperature dependence of the zwitterionic catalyst.

  DOI：

  10.1021/ja307210n
• 作为产物：
  描述：

  5-O-allyl-1-pentanal 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 二异丁基氢化铝 作用下， 反应 0.5h， 以90%的产率得到5-(2-propenyloxy)pentanol
  参考文献：
  名称：

  Yang, Seung Gak; Park, Min Young; Kim, Yong Hae, Synlett, 2002, # 3, p. 492 - 494

  摘要：

  DOI：

文献信息

• Synthesis of novel mimetics of the sialyl Lewis X determinant
  作者：Alexander Toepfer、Gerhard Kretzschmar、Eckart Bartnik

  DOI：10.1016/0040-4039(95)02002-7

  日期：1995.12

  Mimctics of the sialyl Lewis-X determinant in which at least one sugar domain is simulated by a di-, tri- or tetraalcohol unit have been synthesized. The inhibitory potency of these compounds for E- and P-selectin mediated cell adhesion has been evaluated in cell culture assays. The receptor binding affinity of the best of these mimetics was slightly higher than that of the natural oligosaccharide

  已经合成了唾液酸化的Lewis-X决定簇的模拟物，其中至少一个糖结构域由二，三或四醇单元模拟。这些化合物对E和P选择素介导的细胞粘附的抑制能力已在细胞培养测定中进行了评估。这些最佳模拟物的受体结合亲和力略高于天然寡糖配体唾液酸路易斯X的受体结合亲和力。
• The prenyl group: a versatile hydroxy protecting group, removable chemoselectively under mild conditions
  作者：Jean-Michel Vatèle

  DOI：10.1016/s0040-4020(02)00539-2

  日期：2002.7

  6-dicyanoquinone (DDQ) in dichloromethane–water (9:1) are mild and efficient methods to cleave prenyl ethers. These reaction conditions are compatible with the presence of other protecting groups such as acetals, acetates, allyl, benzyl and TBDPS groups. Exposure of aryl prenyl ethers to iodine led to the formation of 3-iodo-2,2-dimethylchroman derivatives in acceptable yields via a tandem Friedel–Crafts/iodocyclization

  二氯甲烷中的碘（在对酸敏感的底物存在3Å分子筛的情况下）和二氯甲烷-水（9：1）中的2,3-二氯-5,6-二氰基醌（DDQ）是裂解异戊二烯的温和有效方法醚。这些反应条件与其他保护基如缩醛，乙酸酯，烯丙基，苄基和TBDPS基团的存在相容。芳基异戊烯基醚暴露于碘导致通过串联的Friedel-Crafts /碘环化反应以可接受的收率形成3-碘-2,2-二甲基苯并二氢吡喃衍生物。两种碘化二甲基苯并二氢吡喃衍生物的简单一步转化就可以合成其中的天然黄酮类化合物：抗氧化剂花椒酚。
• An Efficient and Chemoselective Cleavage of Prenyl Ethers with DDQ
  作者：Jean-Michel Vatèle

  DOI：10.1055/s-2002-20480

  日期：——

  temperature with DDQ in dichloromethane-water (9:1). The reaction conditions are compatible with the presence of other ethereal functionalities such as acetonides, allyl, benzyl, TBS, TBDPS groups. We have also shown that deprotection of prenyl ethers using a catalytic amount of DDQ in the presence of 3 equivalents of Mn(OAc) 3 is a good alternative for the use of a stoichiometric amount of DDQ, albeit the

  在室温下，用二氯甲烷-水 (9:1) 中的 DDQ 可以轻松去除羟基官能团的异戊二烯基 (Pre) 保护基团。反应条件与其他醚官能团的存在相容，例如丙酮化物、烯丙基、苄基、TBS、TBDPS 基团。我们还表明，在 3 当量 Mn(OAc) 3 存在下使用催化量的 DDQ 对异戊二烯醚进行脱保护是使用化学计量量的 DDQ 的良好替代方案，尽管反应时间更长。
• Iodine in Dichloromethane - A Simple Method for Selective Cleavage of Prenyl Ethers
  作者：Jean-Michel Vatèle

  DOI：10.1055/s-2001-18765

  日期：——

  Treatment of prenyl (Pre) ethers of simple alcohols, carbohydrates, steroids, with I2 in CH2Cl2 in the presence of 3Å molecular sieves, constitutes an effective method for their deprotection. This method tolerates other etheral functionalities such as acetals, allyl, t-butyldiphenylsilyl or benzyl groups as well as base labile groups such as acetates. This method applied to a prenyl aryl ether gave rise to a 2,2-dimethylchroman derivative in an acceptable yield.

  用I2在CH2Cl2中，结合3Å分子筛处理简单醇、碳水化合物和类固醇的prenyl (Pre) 醚，构成了一种有效的去保护方法。该方法能够耐受其他醚功能团，如缩醛、烯丙基、叔丁基二苯基硅烷或苄基基团，以及一些基团如乙酸酯等不稳定基团。将该方法应用于prenyl芳基醚，得到了具有可接受产率的2,2-二甲基色烯衍生物。
• Mild deprotection of PMB ethers using tert-butyl bromide
  作者：Nicolas Rival、Arantxa Albornoz Grados、Lucie Schiavo、Françoise Colobert、Gilles Hanquet

  DOI：10.1016/j.tetlet.2015.10.067

  日期：2015.12

  A convenient and high yielding method for the cleavage and scavenging of p-methoxybenzyl protecting group of several alcohols using tert-butyl bromide in refluxing acetonitrile is described. Under these mild conditions other protecting groups such as acid sensitive allyl, benzyl, and Me3CPh2Si ethers, or isopropylidene acetals were unchanged. Interestingly, a selective alkoxy-PMB cleavage was observed

  描述了一种方便且高产率的方法，该方法使用叔丁基溴化物在回流的乙腈中裂解和清除几种醇的对甲氧基苄基保护基。在这些温和的条件下，其他保护基（例如酸敏感的烯丙基，苄基和Me 3 CPh 2 Si醚或亚丙基缩醛）保持不变。有趣的是，在PMB苯氧基醚存在下观察到选择性烷氧基-PMB裂解。