12-hydroxydodecyl acetate | 72156-96-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 12-hydroxydodecyl acetate
• 英文别名: 12-acetoxy-1-dodecanol；12-Acetoxy-dodecanol
• CAS: 72156-96-8
• 化学式: C₁₄H₂₈O₃
• 分子量: 244.375
• InChiKey: QAWLJQBYEWEVOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  12-hydroxydodecyl acetate 在 phenyl-λ³-iodanediyl bis(3-chlorobenzoate) 、 碘 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以62%的产率得到2-(8'-acetoxyoctyl)tetrahydrofuran
  参考文献：
  名称：

  分子内碘催化 C(sp3)-H 氧化作为合成四氢呋喃的多功能工具

  摘要：

  脂肪族伯醇和仲醇的第一个碘催化环化反应通过分子内 C(sp 3 )-H 活化获得四氢呋喃。该反应在使用泛光灯或日光的温和反应下进行。

  DOI：

  10.1002/ejoc.202100652
• 作为产物：
  描述：

  12-((tetrahydrofuran-2-yl)oxy)dodecyl acetate 在 2,4,6-三甲基吡啶 、 三乙基硅基三氟甲磺酸酯 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以88%的产率得到12-hydroxydodecyl acetate
  参考文献：
  名称：

  Mild and Efficient Deprotection of Acetal-Type Protecting Groups of Hydroxyl Functions by Triethylsilyl Triflate — 2,4,6-Collidine Combination

  摘要：

  Deprotection of acetal-type protecting groups of hydroxyl functions has been studied in detail. The treatment of alcohol derivatives protected by acetal-type protecting groups with TESOTf-2,4,6-collidine followed by H(2)O-treatment produces the corresponding hydroxyl compounds in good yields. The characteristic features of the method are very mild and chemoselective, and acid-labile functional groups can tolerate these conditions.

  DOI：

  10.3987/com-08-s(f)88

文献信息

• 1,2-알칸디올의 제조 방법
  申请人：DAEDAL INDUSTRIAL CO., LTD. 대달산업주식회사(120150199426) Corp. No ▼ 195111-0016636BRN ▼608-81-94198

  公开号：KR102109133B1

  公开（公告）日：2020-05-11

  본원은, 1,2-알칸디올의 제조 방법에 관한 것이다.

  本发明涉及1,2-丙二醇的制造方法。
• Facile and highly selective monoacylation of symmetric diols adsorbed on silica gel with acetyl chloride
  作者：Haruo Ogawa、Misa Amano、Haruo Ogawa、Teiji Chihara

  DOI：10.1039/a707753j

  日期：——

  Monoacetylated alcohols of symmetric 1,n-diols are synthesized quantitatively by refluxing a suspension of the diols adsorbed on silica gel with acetylchloride.

  通过对称1,n-二醇吸附于硅胶上的悬浮液与乙酰氯回流反应，可以定量合成单乙酰化醇。
• Selective Monoacetylation of Symmetrical Diols and Selective Monode­acetylation of Symmetrical Diacetates Using HY-Zeolite as Reusable Heterogeneous Catalyst
  作者：Biswanath Das、K. V. Srinivas、I. Mahender

  DOI：10.1055/s-2003-42468

  日期：——

  HY-Zeolite has been found to be an efficient and reusable catalyst for selective monoacetylation of symmetrical diols and selective monodeacetylation of symmetrical diacetates to form the products in high yields.

  已发现 HY-沸石是一种有效且可重复使用的催化剂，可用于对称二醇的选择性单乙酰化和对称二乙酸酯的选择性单脱乙酰化，以高产率形成产物。
• Synthesis and SAR Studies of Neuritogenic Gentiside Derivatives
  作者：Guangfa Wang、Linglin Bian、Hui Zhang、Yanhui Wang、Lijuan Gao、Kaiyue Sun、Lan Xiang、Jianhua Qi

  DOI：10.1248/cpb.c15-00795

  日期：——

  designed and synthesised as a lead compound to treat Alzheimer's disease, based on structure-activity relationships of gentisides. In this paper, the alkyl chain and ester linkage group of ABG-001 were modified. Consequently, several series of novel gentiside derivatives were designed and synthesised, and their neuritogenic activity was evaluated in PC12 cells. Among all the tested compounds, S-dodecyl

  基于龙胆苷的结构-活性关系，设计并合成了2,3-二羟基苯甲酸十四烷基酯（ABG-001）作为治疗阿尔茨海默氏病的先导化合物。本文对ABG-001的烷基链和酯键进行了修饰。因此，设计和合成了一系列新的龙胆苷衍生物，并在PC12细胞中评估了它们的神经生成活性。在所有测试的化合物中，S-十二烷基2,3-二羟基苯甲硫醇酯（15d，命名为ABG-199）是最有效的。该化合物在0.1 microM时诱导明显的神经突长出，与最佳浓度40 ng / mL的神经生长因子和1 microM的ABG-001相当。
• Visible-Light-Driven Dehydrogenative Coupling of Primary Alcohols with Phenols Forming Aryl Carboxylates
  作者：Tairin Kawasaki、Tomohiro Tosaki、Naoki Ishida、Masahiro Murakami

  DOI：10.1021/acs.orglett.1c03017

  日期：2021.10.1

  obtaining aryl esters from aliphatic primary alcohols and phenols was developed. The reaction proceeds under the irradiation of visible light at ambient temperature, dispensing with any oxidant or hydrogen acceptor. Primary alcohols having a variety of functional groups are successfully esterified with phenols. The produced esters can be utilized as the precursor of various carbonyl compounds.

  开发了一种从脂肪族伯醇和酚类中获得芳基酯的制备方法。该反应在环境温度下在可见光照射下进行，无需任何氧化剂或氢受体。具有多种官能团的伯醇成功地与酚类酯化。生成的酯可用作各种羰基化合物的前体。